Men’s Style: A Guide to Men’s Fall Shoes

It’s time for fall gentlemen! Fall is one of my favorite seasons because the earthy colors and layers come out to play, making it extra easy to be stylish. It’s also a great time to dust off your shoe collection and discover new ways to wear them.

I know shoe styles can feel limiting for men, but it’s all about going for colors, textures and prints to really step up your game. Gone are the days where you have your one go-to pair of shoes, now it’s time to have different shoes for your different moods (and outfits!).

Here are my favorite to have in your fall arsenal.



You already know I’m a huge fan of boots, I mean… look at this Ultimate Guide – now that’s passion! Every one of my clients has a couple pairs of nice boots for fall, winter and bring, which come in handy for day to day and dressing up. Let’s make sure you have the right pairs for hitting the sidewalks this fall. If you are need of a new pair, I want you to think outside of the box. The key is to switch it up and go for a new material like suede or introduce a style. Here are a couple of styles of boots i’m loving…

Suede Chelsea Boots

Suede shoes for fall are an excellent choice. You can dress suede up or down and it looks great. The softness of suede goes very well with the season.

STEVE MADDEN Highline Chelsea Boot, Main, color, TAUPE SUEDE

Photo Credit: Nordstrom


Outfit Example:


Photo Credit: Pinterest



Photo Credit: DailyMail

Tip: When wearing slim jeans, let your jeans naturally gather at the top of your boots for a rugged and casual look.

ASOS Chelsea Boots in Gray Suede

Photo Credit: ASOS

If you wear wider leg jeans, you can play around with exposing some of your boot for a rugged and casual style like this…

Black jeans combo with Galeao handmade boots. Iconic silhouette for men outfits

Photo Credit: Pinterest

If you want a more clean look, try cuffing your jeans or chinos like this…

Deer Stags Shoes | Mens(8.5) Deer Stags Tribeca Chelsea Boots | Color: Brown/Tan | Size: 8.5

Photo Credit: Pinterest

Dress pants should always fall straight over your shoes (I.e. no cuffing).

Photo Credit: CarminaShoeMaker

If you want more tips on how to wear Chelsea boots, check out this board.


Brown Leather Work Boot

If you like more of a classic smart casual look, a work boot does the trick because it’s elevated, but not overly dressy.

ALDEN Work Boot, Main, color, BROWN

Photo Credit: Nordstrom

Outfit Example:

Photo Credit: Pinterest

Tip: Cuff your jeans at the top of your work boots for an extra stylish look.

Wish to look tough and gentlemanly at the same time? Best of both worlds! Here is how!

Photo Credit: Pinterest

Chukka Sneaker Boot

If you want to try something completely different, check out these chukka sneaker boots. They are great for the casual guy who want to look effortlessly stylish and keep up his casual vibe.

SANTONI Leland Chukka Boot, Main, color, BROWN SUEDE

Photo Credit: Nordstrom

Outfit Example:


Photo Credit: Pinterest


Tip: Rolled chinos look great with a sneaker chukka

Photo Credit: Nisolo


Really really want to step it up? Check these out…

Saint Boot in Camo side view

Jack Boot in Walnut side view

Photo Credit: Taft

Tip: Printed boots look great with classic blue jeans and a neutral henley or sweater. You want to keep the rest of your outfit pretty minimal, so the attention can go to the boots.

Customer Photo

Photo Credit: Taft

If you want more ideas on how to wear boots, check out this board.


If you’re sick of the same ol’ sneakers, shake it up! Have you thought about sneakers with a bit of flair? By adding some fun prints and accents to your shoes, you can have stand out style without trying too hard. Bonus: if your style is minimalist or very neutral, these will really help you step up your game because they look great with neutral colors. If your style isn’t minimalist, doesn’t matter, these will turn heads and get you some compliments.





Photo Credit: Taft Shoes

Tip: When wearing printed shoes, try to stay in a similar color family of the shoes. For example, the red shoe looks great with an earthy brown or green pant because of the tan in the shoe. You can also pick a color from the shoe and wear it in your shirt if you want to add more color.

model walking in sneaker in red paisley

model in the klay sneaker

Photo Credit: Taft


Brown Leather Sneakers

Sneakers with a bit of flair not your thing? No problem. You might be a classic guy! For the classic guys out there, try adding a nice pair of brown leather sneakers to the mix. Brown leather sneakers add to your look and won’t make you look dressed down. Have you considered a hightop sneaker? Hightop sneakers are great if you are looking for something different. High tops come in handy when the weather cools down too!

Photo Credit: Grenson

Photo Credit: Ace Marks


Think of high top leather sneakers as a more casual boot option. These work great in cold weather and transitional seasons.


Photo Credit: Magnanni


Outfit Example:

Brown sneakers are a great choice!

Photo Credit: I Am Galla

Tip: Brown shoes add a nice pop of color to any outfit. This is especially true if you have a lot of dark or neutral colors in your wardrobe.

Photo Credit: Nisolo

If you want more ideas on how to wear sleek leather sneakers, check out this board.


There’s nothing like soft and rich fabrics as the leaves start falling.  Soft suede gives a feeling of warmth and lightness that should be coveted this season. Whether it’s bluchers, derbies, loafers or even sneakers, add in a pair of suede shoes to keep up with the autumn vibes. Make sure to protect your suede shoes with an all-weather protector and DO NOT wear suede in the rain (the protector will help if the rain catches you by surprise).

Feathercraft Grand Blucher Oxford

Photo Credit: Cole Haan

I’m really digging this suede wingtip sneaker because it’s so unique and eye-catching. You can wear this with rolled jeans and chinos for a unique look.

Screen Shot 2020-08-31 at 7.52.15 PM

Photo Credit: Saks Fifth Ave

Try switching up the color of your shoes and add in colors like blues and greens.

Screen Shot 2020-08-31 at 8.05.52 PM.png

Photo Credit: Sperry

Outfit Example:



Tip: While the weather is still warm, cuff your pants and throw on no show socks with your suede shoes for a stylish end of summer look.

Alright guys, I hope this article has inspired you to step up your shoe game this fall. It’s nice to have a couple of shoes in your rotation so you’re not wearing the same thing over and over again – not only will your shoes age faster, but you’re missing out on life! Also, remember to protect your shoes with a good spray to increase their lifespan. Just like our skin, real leather needs moisture, so apply a conditioner to leather shoes often. My favorite protecting spray is Jason Markk and their cleaner is great too. Here’s a good leather conditioner if you need one.

Feel free to like, comment or share this article if you found it helpful! Make sure you subscribe via email so I can keep you posted when new articles come out.

Catch you in the next one!


Men’s Style: The Ultimate Guide To Boots

From Chukka to Chelsea, boots have become a staple piece in the modern man’s wardrobe. Whether you like to dress up or down, there is a boot out there for every occasion. Wearing a pair of boots with even the simplest outfit can elevate your style.

Photo Credit: Pinterest, Magic Fox, Pinterest

Feel free to read it in order or check out the table of contents to jump to sections.

Too Long; Didn’t Read

What Are Boots

From ankle to sole, there are many parts that help make up a boot’s form. Understanding boot construction is the best place to start since i’ll be using these terms throughout the guide.

Boot Collar: helps minimize irritation of the Achilles tendon and lower calf (depending on the height of the boot).

Hook Fastening: hooks you can put the laces into to further secure the boot.

Upper: literally the upper part of the boot. If you see a label that says “leather upper”, that’s the only part of the shoe that is leather.

Eyelets: the holes that the laces go through.

Stitch Down Construction: where the outsole and boot are sewn together. Stitch down indicates a good quality boot.

Tread: the bottom of the boot, which provides grip.

Insole: refers to the inside sole of the shoe – a good shoe will have a comfortable insole, while cheaper ones might not. However, you can always put your own insole into a boot.

Outsole: outside sole of shoe.

Tongue: the piece of fabric under the laces


Styles of Boots

Boots come in three styles: casual, smart and dressy. Casual boots are meant to be worn when you do not have to dress up at all (i.e. weekend). Smart refers to the Smart-Casual style, meaning these boots can be worn to work, on a date, or anywhere you want to make a good first impression. Dressy boots can be worn to more formal occasions or even with a suit, but are not limited to formal only outfits. I’ll point out these looks in the photos, so you can understand them better.

Casual Styles

Casual boot styles can be worn day to day and don’t offer a formal look to your outfits.

Work Boots

When you think of a work boot in the traditional sense, a steel toe boot might come to mind. However, the modern work boot is a day to day shoe that is perfect for the guy who likes to keep things on the casual side. Work boots are defined by their casual and bulkier style, especially in the toe area which can be reminiscent of the steel toe look. Some popular companies that specialize in work boots are Red Wings, Timberlands and Doc Martin’s, each having their own distinct style of a heavy duty work boot.

Doc Marten Boot

Red Wing Style Boot

Photo Credit: Nordstrom, Nordstrom

Timberland Boot

Classic Suede Work Boot

Photo Credit: Timberland, Nordstrom

Cap Toe Classic Work Boot

You can wear it hiking

Photo Credit: Pinterest, Pinterest

Looks great with casual clothing

Timberland work boot outfit

Photo Credit: Pinterest, Pinterest

Work boots look the best with casual clothing such as jeans and washed chinos. Avoid work boots for any dressy occasions or environments you need to look professional in.

Combat Boots

Classic Combat Boot

Photo Credit: Nordstrom

Rugged style boot

Clean and classic style boot

Photo Credit: Fashion Runway, Bedstu

Dressed up combat boot

Dressed down combat boot

Photo Credit: Pinterest, Thousand Yard Style

Note: If you go for a really minimal black combat boot, you can wear it formally

Combat boots are a style of boot that have more of a military look to them, hence the name. They are defined by their higher length and laces that go up to the very top. Combat boots come in rugged and sleek styles, which are perfect for the guy who wants a little edge in his looks. If the thought of repeatedly undoing and doing laces is already driving you crazy, opt for boots with a zipper on the inner side of the boot.

Hiking Boots

Day to day hiking boot

Photo Credit: Nordstrom

Although the first thought that comes to mind when you hear hiking boots is REI, or any other outdoor gear store, rest be assured there are hiking boot styles that work for day to day. Hiking boots can be defined by their soles because they have visible treads, thick laces, and hook like eyelets. Hiking boots work best with casual wear and are perfect for the guy who likes to dress for nature.

Photo Credit: Fashion Beans, Pinterest

Photo Credit: Bruno Cucinelli

Before you think Hiking boots are only for the very casual, they come in dressy version as well.

Dressed up hiking boot: great for winter

Photo Credit: GQ

If you have a very casual and outdoorsy style, modern hiking boots can be the ones for you. Keep in mind, they do fall in the casual category and should not be worn to any professional or formal occasion.

Smart Casual Styles

Smart Casual styles let you dress up or down your outfits depending on what look you are going for. Jeans make these boots look more casual, while chinos can add a dressier touch.

Apron or Moc Toe Boots

Moc Toe (or Moccasin Toe) boots, also called Apron toe boots, resemble a moccasin shoe with its square shaped toe cap. These boots can range from a casual style, usually with a white rubber outsole, to a smarter style with a wooden outsole. This style of boot looks best with jeans and chinos.

mens apron toe boots brown leather

Wooden outsole = dressed up boot

Photo Credit: McCaren and Sons

Photo Credit: Pinterest, Pinterest

Wooden Outsole = Dressy

Rubber outsole = casual

Photo Credit: J. Crew, Pinterest

Chukka or Desert Boots

The Chukka boot is the perfect starting point for someone wanting to get into the world of boots. They can easily be dressed up or down and go with everything from t-shirt and jeans to business attire. Chukkas are defined by a low eyelet count and ankle length. You might have heard the term “Desert Boot”, which is basically a Chukka, but with a rubber sole. Chukkas are good for dressing up, while a desert boot is good to keep things casual.

Classic Chukka Boot

Photo Credit: DSW

Desert Boot = rubber outsole

Chukka Boot = wooden outsole

Photo Credit: Idle Man, Pinterest

Photo Credit: Pinterest, Ashley Weston

Photo Credit: Pinterest, Pinterest

Chukka boots come in suede fabrics, which are great for a middle point between a leather chukka boot and a desert boot.

Dressy Styles

A classic dress boot can range from being very dressy to somewhat dressy depending on a couple of factors such as the finish, simplicity, and toe style. The more simple a boot, the dressier and more formal it looks. For example, going for a grainy leather finish can make the boot look slightly less formal, while going for a shiny leather finish makes it dressier. Also, a simple outsole can make it look more formal, while going for a contrast outsole (i.e. wood) can make it slightly less formal.

Plain Toe Boots

A plain toe boot doesn’t have a design at the front top of the boot.

Plain Toe = Nothing on the front toe

Plain toe dress boot with contrast sole

Photo Credit: Nordstrom, Allen Edmonds

Photo Credit: Thursday Boot, Pinterest

A simple boot makes it dressier

Photo Credit: Pinterest, Pinterest

Cap Toe Boots

Cap toe boots are defined by a line going across the front top of the boot. The cap toe can be a simple line or have a more decorative one known as “brogue”.

Cap Toe = Line across the front top

Photo Credit: J. Crew, Johnston & Murphy

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest, Pinterest

Brogue Boots

If you like a little more going on in your shoe, a Brogue boot is a great choice. These boots are defined by their decorative perforations such as a wingtip, medallion or cap toe design at the front top of the boot. These boots fall on the dressier side of things and are perfect for suits or simply dressing up your jeans and button down outfit.

Cap Toe: There is a decorative line across the front top of the boot.

Brogue Cap Toe

Photo Credit: Nordstrom

Wing Tip: There is a wing like design on the front top of the boot.

Wing Tip

Photo Credit: Nordstrom

Medallion: There is a design at the top front of the boot. In the example below, you can see two toe styles can be combined, in this case cap toe and medallion.

Medallion + Cap Toe

Photo Credit: Nordstrom

Combination: Two or all three designs can be mixed together into one boot.

Medallion + Wing Tip

Photo Credit: DSW

Brogue boots look great with cuffed jeans

Photo Credit: ASOS, Pinterest

Chinos and brogue boots

This cuff is slightly high, could be lower

Photo Credit: Pinterest, Pinterest

Don’t know where to start? The “safest” place to start is with a plain toe boot because it can be dressed up or down without thinking too much about how the design works with the rest of your outfit. However, if you plan on having a couple of pairs of boots, it’s fun to experiment with different designs. Think of the design as the “bespoke” aspect of your outfit. Refer to the images above on how to best wear a wingtip boot.

Balmoral Boots

If you want a boot for suits and dressy occasions, a Balmoral boot is an excellent choice. The boot is defined by lacing up high at the ankle, hook closure and distinct stitching or contrast fabric between the upper and lower boot. Balmoral boots usually come with a cap toe or wing-tip design.

Balmoral boots have a distinct line that separates the upper

Photo Credit: Bodileys

Photo Credit: Pinterest, GQ

Photo Credit: Pinterest, Splash News

Chelsea Boots

Chelsea boots have a clean and simple toe, which allows them to easily be dressed up or worn with a “smart” look. The shiny leather boot versions do fall on the dressier side of things, but the suede version can be worn with something as simple as a t-shirt and jeans. Chelsea boots are defined by stretchy fabric on either side of the boot, which makes them easy to put on and take off.

Photo Credit: Nordstrom

Photo Credit: Pinterest, Fashion Gens

Photo Credit: Pinterest, Pinterest

Jodphur Boots

Jodhpur boots are a great choice for guys who like a clean boot, but also enjoy a Western vibe. Jodhpur boots are defined by their buckle that hits at the ankle.

Photo Credit: Heddels

Photo Credit: J. Fitzpatrick Footwear, @irvinrandle

Photo Credit: Pinterest, Pinterest

Monk Strap Boots

If you love the look of Monk Strap shoes, well guess what? They come in a boot version too! Monk Straps are defined by their double buckle and can come in everything from plain toe to brogue styles.

Photo Credit: Amazon

Photo Credit: Pinterest, Santoni

Photo Credit: Pinterest, Pinterest

Zipper Boots

If you hate the thought of constantly undoing and doing laces, a zipper boot might be the perfect match for you. Most of the boots I described above do come in zipper versions.

If your boots are lace up, the zipper will be hidden in the inside of the shoe. You do not have to untie your laces if you have a zipper.

Photo Credit: Frye

If you are going the zipper route, opt for a sleek pair of zipper boots rather than a bulkier one. The example below on the left shows a square and bulky style I recommend staying away because they look very old school. However, the example on the right is a better choice because it’s slimmer, has a nice wood accent, and the round-ish toe style is way more modern than a square toe.

Old School and dated

Sleek and modern

Photo Credit: Zappos, Johnstron & Murphy

What Style of Boot Should You Go For?

Alright, now that you know all the styles of boots, which one should you go for? Start by asking yourself if you prefer to dress casual, smart or dressy.


If your overall style preference is casual, it’s best to go for a work boot style shoe. Work boots keep up with your t-shirt and jeans look, but can also go with a button down for those days you want to look smart-casual.

Photo Credit: Pinterest, Pinterest

Smart Casual

If you want a boot that can work for dressy and casual occasions, Chukka boots are you go-to. You can wear them with a t-shirt and jeans or with something business casual.

Photo Credit: Cobble & Hyde, Pinterest


If you prefer an upscale look and find yourself dressing up more often than not, a Chelsea boot is a great starting point since they pair really well with dress pants and even dress up jeans. If the no-lace look isn’t your thing, go for plain toe dress boot with laces.

Photo Credit: @AlexanderLiang, Pinterest

If you like having a bit of flare in your style, go for a boot with a wing tip design. Wing-tip boots can work well with everything from a t-shirt and jeans to suits.

Photo Credit: Norris Dantaford

How To Wear Them

Boots are easy to pair with jeans, chinos and dress pants. If you want to elevate your look, there are small things you can do like cuffing your jeans that can help achieve that.

Jeans and Chinos

Pairing jeans and chinos with boots is an easy look, especially for first time boot wearers. Let’s go over a couple of tweaks you can make to appear more stylish.

Rolling and Cuffing with Boots

There are a couple ways to wear rolled pants with boots and it depends on your boot style. If you boots hit at the ankle, you can roll your pants up to the top of the boot.

Photo Credit: Pinterest, Pinterest

Photo Credit: Swagger New York, Pinterest

If your boot has a slim opening and goes above your ankle, you can roll your chinos to the middle or the top of your boot.

Photo Credit: Pinterest, Pinterest

You can also roll and tuck the front part of your chinos under the boot tongue.

Just front tucked, works with slim pants

Photo Credit: Pinterest

Over Your Boots

If your boots are slim at the ankle, you can wear your pants over your boots for a clean and classic look.

Photo Credit: Pinterest, Pinterest

The Half Tuck

If your boots have a tongue that sticks out (like in a desert boots), you can tuck the pants into the tongue and have the rest of the chino naturally fall to the sides and back.

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest

The Full Tuck

You can tuck all of the bottom of your pants into your boots. Slim pants work better for this look. You can either fold the pant out and then tuck it in like the example on the left. You can also tuck them into your socks and let them naturally fall out as you walk like the example on the right.

Photo Credit: Pinterest, I Am Galla

Photo Credit: Pinterest, Pinterest

Dress Pants

When it comes to dress pants and suits, always wear your pants over your boots. Opt for dressier boots to keep up with the look. Your best options are: Balmoral, Brogue Boots, Plain Toe, Cap Toe, Jodphur Boots, Zipper Boots or Monk Strap Boots.

Photo Credit: Pinterest, D’Marge

Photo Credit: Pinterest

What to Wear With Boots

What to wear with your boots can be broken down by Casual, Smart, and Dressy. You can mix and match the tops, bottoms, and shoes to make something casual look more dressy and vice versa.

A couple of notes:

  • (1) Avoid boots in the casual or smart category with formal suits
  • (2) All boots can go with jeans, but stick to dressy boots for dress pants and chinos
  • Casual: Jeans or Shorts
  • Smart: Chinos
  • Dressy: Dress Pants or Slacks
  • Casual: T-shirt, Henley
  • Smart: Button Down Shirt, Polo
  • Dressy: Dress Shirt
  • Casual: Sweatshirts, Hoodies
  • Smart: Cardigan, Sweaters
  • Dressy: Blazer
  • Casual: Denim Jacket, Bomber Jacket, Parka
  • Smart: Suede Jacket, Leather Jacket, Harrington Jacket, Quilted Jacket
  • Dressy: Peacoat, Over coat

Example Outfits

Photo Credit: Pinterest

Style: Casual
Items: Boots; T-Shirt (Casual); Jean Jacket (Casual); Shorts (Casual)
Stylist Note: When it comes to wearing boots with shorts, it’s best to stick to a desert boot because of its low cut and casual style. Your socks should not show.

Photo Credit: Pinterest

Style: Casual
Items: Boots; T-Shirt (Casual); Jacket (Casual); Jeans (Casual)
Stylist Note: Boots can make even the simplest jeans and t-shirt outfit look stylish. Pair the look with a jacket, in this case a denim jacket, for the perfect layer. The contrasting colors on the boots look great.

Photo Credit: Sobatak

Style: Casual
Items: Boots; Button Down (Smart); Jacket (Casual); Jeans (Casual)
Stylist Note: A work boot with a button down and jeans can keep things on the casual side. Timberlands can still be considered stylish guys!

Photo Credit: Pinterest

Style: Rugged
Items: Boots; Sweater (Casual); Jacket (Casual); Jeans (Casual)
Stylist Note: Boots pair really well with leather jackets and help keep up the rugged look.

Photo Credit: Pinterest

Style: Smart Casual
Items: Boots; Sweater (Smart); Chinos (Smart);
Stylist Note: Chukka boots are a great alternative to dress shoes when you want to look business casual for work.

Photo Credit: Pinterest

Style: Smart Casual
Items: Boots; Button Down (Smart); Chinos (Smart);
Stylist Note: The suede desert boot adds the perfect casual touch to this look, but can easily be taken up to dressy-smart by wearing a leather boot.

Photo Credit: Pinterest

Style: Smart with hint of Bespoke
Items: Boots; Button Down (Smart); Vest (Dressy); Sweater (Smart); Jeans (Casual)
Stylist Note: If you like that classic bespoke style, boots are the perfect footwear to achieve that look.

Photo Credit: Pinterest

Style: Dressy
Items: Boots; Dress Shirt (Dressy); Blazer (Dressy); Jeans (Casual)
Stylist Note: Pairing your jeans and blazer with a sleek pair of Chelsea boots keeps up with the dressy side of things.

Photo Credit: Pinterest

Style: Business
Items: Boots; Dress Shirt (Dressy); Jacket (Casual); Slacks (Dressy); Tie (Dressy)
Stylist Note: Plain toe dress boots work well with slacks and a dress shirt. You can also pair this look with a brogue dress boot.Photo Credit:Pinterest

Photo Credit: GQ

Style: Dressy Casual
Items: Boots; T-Shirt (Casual); Suit (Dressy)
Stylist Note: Suits and boots go really well together and add a non-traditional element to the look. If you need to be formal, go for a plain toe or brogue boot. This look can easily be worn with a dress shirt and tie and still look amazing.

Photo Credit: Soletopia

Style: Dressy
Items: Boots; Dress Shirt (Dressy); Suit (Dressy)
Stylist Note: Wearing Chelsea boots with a suit keeps up with the formal look and is always a safe option if you are unsure what boots to pair with a suit.

Overall Fit

First and foremost, boots should be comfortable. The beauty of going for a good leather boot is it will stretch with your foot as you wear them.


Make sure there is no rubbing at the back of your ankle or leg. Eventually it will break the skin and you will bleed, which is no fun. Sometimes boots can do this at the beginning as this is the “breaking in” period. A temporary solution is to buy a cushioned band-aid and stick it in the irritating area.

Insole & Toe Cap

Photo Credit: Super Feet

Your foot should fit comfortably in the insole. It should not be able to move back and forth. However, make sure your toe isn’t up against the front of the shoe, there should be a little room. Do not buy boots that are too large because your foot and boot’s flex point should line up. The flex point is the curve in the middle of your foot at the bottom. If they do not line up, you can cause harm to your foot.

Make sure your toe isn’t hitting the top of the boot. That means the shoe is too small for you and you need to move up a size. You should have wiggle room. If you have wide feet, opt for a “W” size boot.

What a Cobbler Can Fix

Just like there is a tailor for your clothes, there’s a cobbler for your shoes. Here are some things they can fix for you:

  • Shoes too tight: A cobbler can stretch out your shoes. They have a machine at their workshop that can target a specific area to stretch. This includes a pinching toe, tight heel or tight calf.
  • Replace Sole: Whether you’re in need of a brand new sole or don’t like the one your current boot comes with, a cobbler can resole your boots. If you love your boots and they are a bit slippery at the bottom, a cobbler can put in a no-skid sole for you. Your soles must be resoleable, so it’s best to ask if they are when you buy your boots.
  • Uncomfortable Insole: a cobbler can add padding to your insole.
  • Smelly boots? Don’t need to toss them. A cobbler can professionally clean your boots inside and out. You can also get a spray for the inside of your boots, there are some good ones out there
  • Waterproof your boots: Alright, if you’ve ever lived in a rainy or snowy area, you know the feeling of wet socks. Well, a cobbler can protect your shoes from the elements!

What You Can Fix

There are certain things you can do at home to protect or refresh your boots.

  • Protect your boots with a leather and suede protector. The spray creates a protective barrier that will stop scratches or stains to sink into your boots. You can also buy waterproofing spray, but don’t expect it to get you through a torrential downpour for 5 hours.
  • Boots smell? Get a deodorizing spray to keep them lasting longer.
  • Add in your own insoles if the inside of your boot isn’t comfortable.
  • Stretch your boots with a leather stretching spray.

What to Look for in a Boot

When it comes to boots, there are a couple of things you should look for if you are “investing” in them. Details like types of leather and stitch down construction can help your boots last longer and make sure you get more bang for your buck. If you are not looking to “invest” in a pair of boots, look for comfort and style.

Types of Leather

Knowing what a “good” vs “bad” leather is will help you spend wiser. Keep in mind, i’m not telling you to spend a ridiculous amounts on boots, but what I am telling you is to make sure you’re not overpaying for something that isn’t as good.

Full Grain

Image result for full grain leather
Photo Credit: Signature Leather

Full grain leather is the best in class. If you see this on the boot, it’s a great sign. Not only is it the strongest and most durable leather, it ages well and resists moisture.

Top Grain

Top grain leather is a step below full grain leather. It’s not as durable because the top layer of the leather has been sanded down to make it look more uniform. However, it’s not a bad choice compared to some other leathers out there.

Bonded Leather

It’s exactly what it sounds like, leather scraps that are bonded together to create a sheet of leather. Although it’s technically real leather, it’s not as durable as full grain or top grain. Don’t spend a lot on these.

Genuine Leather

This term sounds amazing, but sorry guys, it doesn’t mean what you think it does. Genuine leather is made from the bottom cut, but doesn’t have any grain and is heavily processed. So yes it is leather, but it’s not good leather. You might be better off buying faux leather. Don’t spend a lot on these.

Corrected Grain Leather

Image result for full grain leather examples
Photo Credit: Ozapato

This leather can look fancy, but it’s actually low quality leather that has been printed with fake grain to make it look luxurious and real. Don’t spend a lot on these.


If you see a really cheap pair of “leather” boots, double check the label, they might be polyester. Polyester can look like real leather, but it’s a synthetic material. Make sure you don’t spend a lot on these.

Leather VS Suede


Suede and Leather are generally the same material, which is cow hide. However, Suede is the inside of the hide whereas leather is the outside of the hide. Suede can also come from sheep and pigs.

Image result for full grain leather
Photo Credit: Jackson Wayne Leather Goods

Dressy Factor

Suede and Leather are generally the same material, which is cow hide. However, Suede is the inside of the hide whereas leather is the outside of the hide. Suede can also come from sheep and pigs.



Photo Credit: Gant, Taft

Suede Dressed Up

Leather Dressed Up

Photo Credit: Pinterest, GQ

Note: An easy rule of thumb to remember is: if you are trying to be formal, go for a darker boot. Dark does not mean only go for black, but going for a dark brown, dark burgundy etc.

What’s Better?

If you’re looking for durability, you probably shouldn’t go for suede because it is more fragile and will get damaged when it comes in contact with water. However, if you are going for pure aesthetics, suede is pretty good looking! Suede might not be your day to day shoe, but it can definitely be a nice boot to have in your wardrobe.

Stitch Down Construction

Photo Credit: Truman Boot Company

See the white stitching? That’s stitch down construction. If your boot has this, excellent! It’s a marker of a good pair of boots. This stitching connects the upper boot to the sole of the boot. What’s neat about this style of stitching is it allows you to resole your boots if you need to, making them last for years on end. Other words used for stitching: Norwegian Welt or Goodyear. The alternative to stitching is a glued down sole, which as you can imagine, will eventually detach from the boot.


Photo Credit: Real Men Real Style

If you live in a place where there are cold and wet winters, having good treads on your boots is going to save you a lot of slips. You can always get a cobbler to add treads if your current pair doesn’t have them.


For your first pair of boots, go for either black or brown since they are a staple color to have. Black and brown boots are very neutral and go with everything.

Classic Colors

When buying your first pair of boots, go for classic colors like brown, black or grey.



I can safely say brown leather boots go with almost every outfit under the sun. Think of brown boots as a pop of color in your outfit. For example, if you’re wearing all dark colors (i.e. black t-shirt and dark blue jeans) a brown boot is great for breaking up the darkness and bring your outfit to life.

  • Brown boots work really well with neutral, earthy, bold and bright colors
  • Medium brown boots are an excellent choice
  • Brown boots work for formal occasions as long as the boot is dressy

Photo Credit: Pinterest, @krueger_patrick

Photo Credit: Pinterest, The Fine Young Gentleman

Photo Credit: Pinterest, Rowanrow

Photo Credit: Pinterest, He Spoke Style


Suede brown boots can be a little tricker to pair, but the key is to stick to neutral and earthy shades in the rest of your outfit.

  • When wearing light brown suede boots, it’s pleasing to the eye if there is another piece in your outfit that is light as well (i.e. shirt, pants etc).
  • Medium to dark brown suede boots go really well with earthy or deep colors
  • If you like bright pants for Spring, light to medium suede boots work great

Example of light boot with light shirt

Medium brown boots work well with earthy colors

Photo Credit: Royal Fashionist, @chrissleman

Photo Credit: Pinterest, Styleoholic

Photo Credit: Pinterest, Pinterest


Just like brown, black boots go with almost every outfit under the sun. If you’re not sure where to start, black is a great option.

  • Black boots are great for more formal outfits like suits
  • Black boots with broguing or a wooden heel is a great option to add flare
  • Brown boots work better with lighter colored bottom (i.e. light blue), black might be too harsh with a soft color
  • Black boots are great for guys who like a bit of a “motorcycle” edge in their looks
  • Black suede boots are a great option if shiny black seems too formal for you

Photo Credit: Idle Man, Idle Man

Photo Credit: Pinterest, @magicfox

Photo Credit: @magicfox, Pinterest

Photo Credit: Pinterest, Pinterest


After you have your black or brown pair of boots, grey is a great color to add into your rotation. In terms of pant colors, grey boots work with other neutral colors like blue, white and black, and pair really well with earthy colors like burgundy and green.

  • The easiest way to wear grey boots is by having a 2 neutral colors and one pop color (i.e. white t-shirt, blue jeans and green jacket). Don’t go past 3 different colors in your clothes
  • You can also wear all one color (i.e. all black or all blue) and have the grey boot be the pop of color
  • Don’t wear the same shade of grey in your pants and shoes
  • You can wear opposite shades like dark grey pants and light grey boots
  • You can wear a grey top (i.e. sweater or coat) and grey boots of the same color and it will look fine since the two items are away from each other

Photo Credit: Pinterest, @magicfox

Photo Credit: On Point Fresh, Style Mann

Photo Credit: Hello His, Pinterest

Other Colors

After you’ve covered your basic colors, you can have a little fun and experiment with secondary colors that can take your look to the next level.


Although they are more rare, green boots are a unique color to add into your rotation. The key is to let the green boot be the statement piece in your outfit and you can do this by wearing dark or neutral colors with the boots.

  • Blue, black, beige and white bottoms pair the best with green boots
  • When wearing green boots, it’s best to pair them with earthy or neutral colors
  • Green suede boots are an excellent fashion forward choice

Photo Credit: Pinterest, Alden

Photo Credit: Pinterest, Pinterest


If you really want to stand out of the crowd, white boots can be a fashion forward statement. Only word of warning: good luck keeping them clean!

  • The best way to wear white boots is with neutral colors like blue, black, white and grey
  • Cream boots can be a good alternative if white seems too bold

Photo Credit: Pause Magazine, Timberland

Photo Credit: Pinterest


Burgundy boots can go two ways: classic or fashion forward. A leather burgundy boot is the classic choice because it can be worn exactly as a medium brown boot would. However, a brighter burgundy boot is great for making a fashion statement.

  • Burgundy goes really well with other earthy colors
  • Can treat a burgundy dress boot like a brown dress boot
  • Perfect way to add a splash of color to your boots without going overboard

Photo Credit: Pinterest, J. Crew

Photo Credit: Fabripagllari, J. Crew

Photo Credit: Pinterest, Thousand Yard Style


If red isn’t your thing, maybe blue is! Blue boots can be a fun color to add to your collection. Navy boots can be as subtle as black, but lighter blue boots can be your statement piece.

  • The best way to wear blue boots is with blue, black, beige or green bottoms and a neutral top
  • If you like blue, but don’t want the whole boot to be blue, go for a blue accent in the heel
  • A darker blue will be easier to pair than a lighter blue

Photo Credit: Pinterest, Pinterest

Photo Credit: Pinterest, Pinterest

Photo Credit: Look Book


Taking care of your boots will help them last longer, especially if you are going for full grain leather or suede. I know sprays and lotions seem like a marketing ploy to up-sell you, but some of them really work.

Overall Protection

The first thing to do is spray your boots with a Leather and Suede Protector.A protector will prevent scuffs, stains from setting in, and any water damage. You only need to spray your boots once a month. A universal protector will do the trick.

If you are “investing” in your boots and going for real Leather or Suede, follow the rest of the instructions below:

Leather Care

  • Just like our skin, leather needs moisture, so apply a good leather conditioning cream to the boot from time to time.
  • A damp wet cloth can help clean leather.
  • If your leather gets wet, let it dry naturally.
  • Get your boots shined from time to time.

Suede Care

  • You can brush your suede before and after applying the protector spray.
  • Small scuffs to your suede can be erased with a rubber eraser or a toothbrush.
  • If the stain is liquid, try using cornmeal or talcum powder on the spot. If it’s dry, try white vinegar (vinegar works great for salt stains as well).
  • Get a good suede brush to rejuvenate the fabric! Holding it above steam and then brushing can help the driest of suede come back to life.

Note: Keep in mind, water and suede don’t mix, so avoid wearing them in the rain or putting water directly on them when cleaning.

Shopping Notes


Your boots are made for walking, make sure you can walk hours on end in them. An excellent insole will help with this. Add your own insole if you like the boot overall, but wish the insole was a bit more cushioned.

Boots You Can Resole

If you are “investing” in your boots, make sure boots are resoleable. If 5 years down the line the only thing that’s messed up is the sole, you can make them anew!

Know What You Are Getting

You don’t need to buy the most expensive boots, but just make sure you’re not being ripped off.

Take Care of Them

Take care of your boots. Get good cleaners and protectors and apply them every one or two a months depending on how much you wear them.

Avoid Flashy Brands and Go for Quality Brands

Go for a brand that has a good reputation. There are new and old brands that make excellent shoes. Beware of flashy brands that will charge you for the label rather than quality.

Real Leather Stretches

Real leather stretches slightly as your wear it, so don’t buy your shoes too big. If you are getting a brand new pair of boots, chances are 0 to a few people have tried them on before, so expect them to be a bit snug at first. If you already bought boots and they stetched out on you, add in an insole to make them tighter.

Look at Customer Reviews for Sizing and Fit

If you’re shopping online, pay attention to customer reviews and how sizing worked for them (i.e. runs large or runs small) and order accordingly. Sometimes the description says true to size, which is not always the case. The example below shows the store’s fit note and the customer’s fit note, which are the opposite.

Says “True to Size”
Customer Reviews Say They Fit Big


What’s better round or square toe?

When it comes to dress boots, a slight round toe is the better and more modern option. Square toe can be hard to pull off because it looks too trendy and odd with jeans. Moccasin boots are the only exception because that’s how they are meant to be.

Photo Credit: Amazon, Johnston & Murphy

Can men pull off rain boots?

There are 2 ways to approach rain friendly boots: you can go for low cut rubber boots or find a pair of leather boots that are waterproof. I recommend going for the latter because you can wear them day to day and on rainy days. Rubber boots, on the other hand, can get hot and heavy, making you want to switch out of them once you get indoors. While shopping online, use the keyword “waterproof” and the style of boot you like (i.e. waterproof chukka) and you will find some nice options. Spray your waterproof boots with a protector to make them last longer.

Waterproof Chukkas

Rubber Boots

Photo Credit: Zappos, Zappos

Waterproof Apron Toe Boots

Photo Credit: Timberland

Can’t I just spray my regular boots with waterproof spray to make them waterproof?

Waterproofing sprays are made more for protecting the skin of your boot, rather than sealing the seams to prevent water from seeping in. If you are caught in light rain, it could work. However, if you get caught in a downpour and have a mile to walk, you’ll probably have wet feet by the end.

What should I look for in a boot?

  • Start with comfort. Boots should be comfortable, so you can wear them for hours. The footbed should fit your foot well. You can always put in your own insole if you’re getting a great deal on an excellent pair of boots, but the bed is a little off.
  • Next, quality. Fabric and stitch down construction are the other key factors that will determine whether you have a good boot or not. You don’t need to spend hundreds on a full grain leather boot if you don’t want to, but make sure you’re not paying a high price for bad leather.
  • Spending $200 to $300 on a good boot that will last you for years is worth the investment versus spending $80 on boots and having to replace them often. Also, who wants uncomfortable cheap boot that you have no desire to put on. Now that’s really wasting money.
  • If shopping online, find a place that has free shipping and free returns, so you can order 2-5 of your favorite pairs and have a try on session at home.

Can I wear boots with shorts?

Generally, I would say avoid wearing boots and shorts. However, there is one exception and that is a desert boot or suede chukka boot because they don’t go up the ankle as much. It’s best to wear low cut socks to keep up with the “summery” look.

Desert and Chukka boots with shorts

Photo Credit: Pinterest, Pinterest

If you don’t want to look like a mailman and also get a very bad tan line, avoid the following:

Avoid any high boots or socks with shorts

Photo Credit: Pinterest

You made it to the end of the guide. You’re a boot expert now! If you have any questions, don’t hesitate to reach out. Happy Boot Shopping!

Men’s Style: Why You Should Have Dressy Sneakers

Nothing kills an outfit like the wrong shoes. I see it all the time, guys wearing running shoes with a giant athletic logo splashed across the side with their day to day outfits. Guys, please don’t do this. Save your running shoes for the gym, there’s a much better looking and equally comfortable solution that should have your attention instead: The Dressy Sneaker. You’ve probably seen me mention “dressy” sneakers as a wardrobe must and they are! In this post, I’m going to dive a little deeper to explain exactly what is a “dressy” sneaker and how and when you should wear them.

Don’t let the word “dressy” throw you off, it’s just a way to describe a sneaker not meant for the gym or other athletic activities. Instead, dressy sneakers are great for day to day wear like hanging around town, coffee shops, brunch, bars, casual dates, picnics, running errands, day parties, casual work environments, traveling etc. Alright, let’s dive in to the wonderful world of dressy sneakers!

What Are Dressy Sneakers?

When the word sneaker comes to mind, it’s easy to think of your classic Nike or Adidas brightly colored running shoes. There is nothing wrong with those shoes, but I don’t want those to be your go-to shoes for casual wear. Dressy sneakers are more sleek and subtle by usually being solid in color, made of leather or suede, and have a 1 inch flat rubber sole.

Compare the footwear in the image on the left and right…. Good Example


Photo Credit: Pinterest, I Am Galla

The right looks so much better and way more intentional and put together. The one on the left looks amateur.

How Do You Wear Them

Whenever you want to dress casually or dress down a dressy look, your sneakers can help you achieve this without sacrificing style. Whether it’s t-shirts, henleys, button downs or jeans, chinos or shorts, your sneakers will work with all your looks. To better explain how to put your outfits together, let me breakdown a couple of looks for you.


Photo Credit: Pinterest

Outfit Breakdown: Sweatshirt, joggers, white sneaker

Note: The white sneakers make this very casual look very well put together.

Photo Credit: Primer Magazine

Outfit Breakdown: Henley, cardigan, jeans and sneakers

Note: This is such an easy and comfortable look and the rolled up jeans and sneakers pull the look together perfectly.

Photo Credit: D’Marge

Outfit Breakdown: Bomber jacket, t-shirt, shorts and sneakers.

Note: The beauty of sneakers is they can go with shorts and make a very casual outfit look very stylish and sophisticated.

Photo Credit: Pinterest

Outfit Breakdown: Casual denim shirt, white t-shirt, rolled up black jeans and white sneakers

Note: If you’re into the unbuttoned shirt look, your sneakers will work really well with it.

Smart Casual

Photo Credit: He Spoke Style

Outfit Breakdown: Leather jacket, tucked in button down, chinos and leather sneakers.

Note: If you like looking a little more dressed up, your sneakers can keep the look relaxed, but still sophisticated.

Photo Credit: Pinterest

Outfit Breakdown: Crew neck sweater, casual slacks, brown leather slip on sneakers.

Note: If you want to make the most of your slacks, you can dress them down by wearing no show socks and sneakers. If you hate laces, this is a great example of slip on sneakers instead of lace ups.

Photo Credit: I Am Galla

Outfit Breakdown: Button down, chinos, brown leather sneakers

Note: If you love a classic button down and chinos look, your sneakers can help make this look weekend friendly.

Photo Credit: Pinterest

Outfit Breakdown: Casual blazer, t-shirt, chinos and white sneakers

Note: This is the perfect example of how sneakers can make a casual blazer look very comfortable, stylish and weekend appropriate.

Photo Credit:

Outfit Breakdown: Half sleeve button down, rolled up chinos, no-show socks, and white leather sneakers

Note: I love this look for summer, it’s so stylish and easy to wear. You will be sure to stick out of the crowd in a very stylish way.


Outfit Breakdown: Casual suit, dress shirt, sneakers

Photo Credit: Lifestyle By PS

Note: If you’ve ever wanted to wear a suit casually, your dressy sneakers will help you achieve it.

Photo Credit: Lifestyle By PS

Outfit Breakdown: Casual suit, dress shirt, sneakers

Note: Curious to try a t-shirt and casual suit look? Throw on a pair of dressy sneakers and you’ll be good to go! Jay-Z (the rapper) wears this look a lot and I love it. The key is to wear a cotton or other casual fabric suit.

No Show Socks

Photo Credit: Pinterest

Wearing no show socks when you’re wearing joggers or rolling your pants with your sneakers is going to earn you 100x style points. This small detail shows you know how to rock a pair of dressy leather sneakers the right way. No-Show socks can be purchased from anywhere. The key is to have a rubber backing in your sock to prevent them from slipping. Trust me, the most annoying thing is when you need to constantly pull up your no show socks. Here’s what I found on Amazon!

How To Lace Them

Some laces end up being very long and you end up getting a giant bunny loop situation happening in your shoes, which throws off the clean and sleek look. It happened with a client of mine, he had these beautiful black dressy leather sneakers on and every time he’d try them on with an outfit, something was putting me off. I couldn’t quite figure out what it was that made them look very amateur and young. I took his shoes and hid the bunny loops behind the tongue of the shoe and he slipped them on. Boom! There it was, the amateur look was gone and a minimal sleek sneaker was shining in all its glory. He was even blown away of how big of a difference this small detail made.

Photo Credit: Pinterest,

The laces on the left look terrible, the laces on the right look so sleek!

To achieve this clean look, try the “Display” shoelace method.

Photo Credit:

“Display” refers to how stores set up their shoes to look nice and sleek. The key have the very top of the laces go into the lace hole rather than come out. You can tie the laces behind the tongue and make them slip on shoes. Additionally, you can get Shoelace Lock Clips, so you don’t have to constantly re-tie your shoes.

Slip-On Sneakers

If you hate the thought of laces all together, you can go for dressy slip on sneakers. You can wear them exactly the same as lace up sneakers.

Photo Credit: The Style City

Slip on sneakers look slightly more casual than sneakers with laces, however, they can achieve a very similar effect. Who doesn’t want shoes that are easy to slip in and out of?

Hybrid Sneakers

Hybrid sneakers are interesting mix of dress shoes and sneakers. They offer a stylish and unique look if you’re ready to step up from a simple sneaker. Hybrid shoes have the look of a dress shoe (i.e. oxford, derby, monk strap etc.) at the top, but the sole of a running shoe. My personal favorite is the hybrid monk strap sneaker.


Photo Credit: Cole Haan, Florsheim

The photo on the left is an Oxford Hybrid Sneaker. The photo on the right is a Monk Strap Hybrid Sneaker.


Photo Credit: DG Manila, Pinterest


The key is to wear no shoe socks and ankle pants to make this look modern and sleek. You can wear this style of sneaker with a blazer and chinos for a Smart Casual look as well.


My top recommendtions for dressy sneaker colors are: white, black, grey or brown. These neutral colors will go with almost all of your outfits. Let’s look at the colors in more detail!


Photo Credit: Common Projects

White is pretty classic when it comes to dressy sneakers. You will notice the majority of my photos had white sneakers because those are the ones that look the freshest. However, they do require a bit more maintence because you want to keep them white and clean. If you’re up for the challenge, I personally say white sneakers look the most stylish.


Photo Credit: Greats

If white makes you feel overwhelmed, go for black sneakers instead. They’ll go with everything and be easier to maintain.

Brown or Burgundy

Photo Credit: Magnanni


I personally love brown sneakers, especially when they have a “wood” finish like the example above. They are great for breaking up dark outfits and are more rare than black and white.

Photo Credit: To Boot New York

If you want something softer than black, but not as bright as white, try grey! Grey shoes are very neutral and will go with a lot of colors. Grey suede is a favorite of mine because it has a softer effect and looks very classy. However, you never want to wear suede out in the rain because it will get ruined. Alternately, grey leather is a great option if maintaining suede scares you.


Photo Credit: Amazon

Get a protect all spray (left) and an odor spray (right) .


The more you take care of your shoes, the longer they will last. Clean your shoes every couple of months (or when they start looking a bit worn) and spray them with a water-repellent protector. Protectors are great because if you spill anything like red wine on your white shoes, the drops will slip right off. I like the Jason Markk spray because it doesn’t yellow your shoes like some sprays can.

Dirty laces are a style killer, so make sure your laces look fresh. You can wash your laces if they start to look dirty. However, if they are really looking worn, replace them.

If you have a tendency to ruin your shoes because of odor, keep a odor fighting spray around and spray them after a couple of wears or more often if you need to. I personally like this Spray. It’s normal for shoes to smell eventually, especially if you are wearing thin socks. Don’t ever not wear socks for the no-show sock look, you will ruin your shoes much faster.

When Are Dressy Sneakers Appropriate?

Just because they are considered a “dressy” sneaker, doesn’t mean you should be wearing them at formal events or parties. Save your leather sneakers for your casual and smart-casual outfits. If your workplace is casual, you can wear them there.

The casual suit look with sneakers is best for weekend or vacation, when you want to look sleek and relaxed. Day time parties are great for this look as well!

When Are Actual Running Shoes Okay?

For the most part, save them for the gym or athletic activities. However, if your outfit is very casual like joggers or sweatshirts, you can wear your running shoes out and about. When you are wearing jeans or chinos, don’t wear your running shoes. I know sneakerheads won’t agree with me on this, but we’re aiming for smart and classic styles, not trends.

My Top Sneaker Picks

Dressy leather sneakers can range anywhere from $50 to $500, depending on what you are looking for and your budget. The most important thing to look for is comfort since you’ll be wearing these instead of your running shoes. Try a couple of different brands on to see what fits your foot the best. There are new brands popping up everyday specializing in dressy sneakers, so it’s best to order a couple of pairs and see what fits the best. Here are a couple of my top recommendations going from the lowest to highest pricetag:

Adidas Stan Smith or Neo ($45+)

Photo Credit: Adidas

Adidas is a classic brand that comes to mind when it comes to sneakers. They have their Neo white on white sneaker that is super clean and at a low price point. The Stan Smith is their more popular one, which will run you about $75.

Cole Haan Crosscourt ($70+)

Photo Credit: Cole Haan

Cole Haan makes really lightweight classic dressy sneakers at a good price point. You can typically find them for $70 to $100, depending on if you can get them on sale. Cole Haan also plays around with hybrid sneakers a lot.

Ecco Soft 8 ($150+)

Photo Credit: Ecco

Eccos are one of the most comfortable shoes you will probably try on. I especially like their Danish collaboration for very minimal and sleek sneakers. Eccos will run you about $150, but you can sometimes find them on sale.

Greats Royale ($180)

Photo Credit: Greats

Greats is a Brooklyn based brand that has been around for a couple of years and produce excellent quality Italian sneakers. They have a weatherproof version too! Greats will run you about $180 for the classic leather sneaker, but you will get free shipping, free returns and great customer service. If you sign up for their email list, you can get 10% off.

To Boot Knoxx ($325)

Photo Credit: To Boot

If you’re ready to invest in your sneakers and absolutely love quality and crafttmanship, To Boot makes an excellent dressy sneaker. If you love the suede look, they have a couple colors out every season. They will run you about $325. Keep a look out for them on sale.

Magnanni Elonso ($325)

Photo Credit: Magnanni

Common Projects ($400)

If you’re ready to splurge, Magnanni is an Italian brand that nails the dressy leather sneaker as well. I love their wood finish sneaker I showed in the brown category as well as the clean look they offer. You can sometimes find them on sale, so keep a look out. These will run you about $325.

Photo Credit: Common Project

If you’re looking for the trendiest brand and quality dressy sneakers, Common Projects could be for you. They are handmade Italian sneakers that became very popular in the last couple of years. Be prepared to spend a shiny penny, but they do look pretty sleek and have a cool logo. Common Projects will run you about $400.

There you have it, one of the easiest and most comfy swaps you can make in your wardrobe to look modern and stylish. Hope you enjoyed the post! Feel free to reach out if you have any questions or want me to tackle other burning questions you may have.

If you loved this post, make sure you subscribe to my email list, so I can let you know when the next one is out!

Men’s Style: Rain Friendly Footwear for Men

It’s raining, it’s pouring… and you don’t have the right shoes to go outside. Sounds like a dilemma every guy has experienced before. Now, you could opt for a classic pair of rubber boots, or as the British call it, Wellies, but rubber boots can be a drag. The problem with rubber boots is they are heavy, not breathable, and require you to change out of as soon as you get to your destination.

Well, I have a better and more stylish solution for you: welcome to the wonderful world of waterproof shoes and boots!

Before we get started, please note: “water-resistant” and “waterproof” are two different things. Water-resistant means it can stand being in water for a limited time (i.e. walking from A to B while it’s raining), while waterproof means you can be in a downpour for extended periods of time and zero water will seep in. Keep these terms in mind when you are searching for your perfect pair and decide what your needs are.

Alright, let’s see what I have for you…

Waterproof Sneakers

Photo Credit: Zappos, Greats

All weather sneakers are pretty cool and are a subtle way to protect yourself from the elements. They look like ordinary sneakers, but are made with water-resistant or waterproof materials. You can go for a high-top, which goes up to your ankle, or a low top, which stops below your ankle. If you’re a casual guy and your go-tos for the weekend (or even work) are casual shoes like sneakers, these will work great for you.

If you prefer a water-resistant sneaker, opting for a sneaker made out of wool can deliver style, protection, and breathability. Best of all, you can wear your wool sneaker day to day and not just on rainy days.

Waterproof Casual Boots

Photo Credit: Zappos, Timberland

Photo Credit: ZapposClassic Work BootIf you live in an area where it snows, boots are a better option than sneakers, for winter at least. A casual boot, like a “work boot”, is perfect for the guy who has an overall casual style (i.e. wears jeans and t-shirts most of the time). These boots will give you excellent grip, protect your feet from wetness and make sure you look stylish. Bonus: you can take them hiking!

Waterproof Smart-Casual and Dressy Boots

Photo Credit: Nisolo, Cole Haan

What if I told you there is a stylish boot you can wear to work and it’s waterproof? They exist! Waterproof boots come in many styles including Smart-Casual and Dressy ones. Waterproof Chelsea and Chukka boots, for example, are perfect for those who don’t want to change into different shoes when they get to their destination. Going for a waterproof version of your favorite boot style will pay for itself because you can wear them day to day too.

If you want to learn more about different boot styles to see which one appeals to you, check out The Ultimate Guide to Boots where I give you the who, what, where on boots.

If you weren’t convinced before, there you have it: plenty of stylish water friendly shoe options besides rubber boots to get you through wet weather. Whether it’s April showers or severe winter weather, you’ll be ready to take on the elements best foot forward.

Men’s Style: Guys, Let’s Chat Sandals

If I told you there’s such a thing as stylish sandals, would you believe me?

Whether it’s summer or vacation, a lot of guys are stuck thinking they can’t show their feet. Or, what’s worse, they put on out of date camping sandals and ruin a completely acceptable outfit. Never fear, I’m here to set a couple of things straight (1) you can wear sandals and (2) there are certain styles of sandals that are more stylish and modern than others.

First, Let Me Tell You What To Avoid

Photo Credit: Zappos, Zappos

Photo Credit: Zappos,

Look, I get it… they’re comfortable. But please, don’t wear these styles of sandals unless you are going camping and crossing through rivers and jumping in swimming holes. These sandals scream old Dad sandals and I won’t let you be that guy.

Alright, now that I’ve broken your heart and told you what to avoid, let me show you what looks good!

Classic Styles


Photo Credit: Zappos, Zappos

Hey, look! They’re comfortable and yes, they’re stylish! Birkenstocks are on my “yes” list because besides being comfy, they can look stylish with the right outfit. Pros: they’re masculine, great quality, and are easy to slip on and off.

Photo Credit: Idle Man, I Am Galla

Leather or Canvas Flip-Flops

Photo Credit: DSW, Abercrombie

Yes, you read it right. I said flip flops. Flip flops can be stylish! The key here is to go for leather or canvas straps rather than cheap rubber ones. If you’re going to the beach and planning on getting them dirty, yeah, go for rubber, but if you’re on wandering around the boardwalk on a beautiful summer day, go classy with the leather or canvas.

Photo Credit: Idle Man, The Subtle Things

Fashion Forward Styles

Buckle Sandals

Photo Credit: Zappos, Zappos

They’re sleek, minimal, and stylish. If I see a guy wearing these, he exudes confidence and good taste. Best of all, they pair really well with button downs and shorts without taking away from an otherwise smart-casual look.

Photo Credit: Fashion Beans, Pinterest


Photo Credit: Nordstrom, Dune

Slides are perfect for the guy who likes the leather sandal look, but wants to be able to slip his shoes on and off quickly. Going for leather slides really classes up the look. However, if you are planning on walking around a lot, a buckle sandal might be more comfortable.

Photo Credit: Nordstrom, Pinterest

Can I wear socks with my sandals?

NO. Unless you’re on the New York Fashion Week catwalk and walking for some high end brand who is trying to make a statement, don’t do it.

Or, if you’re trying to go all out artist… maybe. But notice he has fun printed socks that go with his “hipster” look. I doubt you’re trying to achieve this look, so stick to my first answer: avoid.

And don’t be fooled into thinking you can pull them off with your athletic white socks… you will look like this:

Besides repelling people, you will get a pretty bad tan line. So, just don’t do it.

But my feet… they’re ugly.

Look, people don’t care about how your feet look, so let them be free! Unless, of course, the person you’re with has some weird pretty feet fetish, well, that’s a different story. Other than that, you’re good! If you’re paranoid about your feet, get a pedicure. Pedicures are relaxing, a lot of guys get them, and they’ll make your feet so fresh and so clean. You’ll thank me once you do it. Lastly, keep your toenails trimmed, people notice that more than anything else.

With Spring/Summer on the horizon, warm weather and vacations call for summer footwear aka sandals. Don’t be shy, wear them and rock them! Hope you enjoyed the post!