Men’s Style: The Perfect Smart Casual Starter Wardrobe

Not knowing where to start is a huge pain point for anyone trying to get their wardrobe together. It can feel overwhelming and expensive, but it doesn’t have to be! Whenever I have a client that is starting from scratch, meaning most of their wardrobe is outdated and they want to start anew, I have a formula I like to follow. The formula ensures their needs are met and they have numerous combinations to wear day in and day out. The formula is as follows:

Starter Wardrobe = Perfect Dozen Shirts + 3 Pairs of Jeans + 1 Chino + 1 Jacket + 2 Shoes

This formula allows for a minimum of 50 outfits to start off with and, moving forward, we can add a piece at a time to create more. That number can be doubled if we stick to a specific color palette, making it more of a capsule wardrobe. A capsule wardrobe is when all the tops go with all the bottoms, but it limits you with what colors you can work with. With my system, I like for my clients to have a variety of colors, so I go as capsule as I can with a few easy exceptions.

If you are doing this on your own, you don’t have to buy everything at once. Instead, use this formula as a blueprint to make targeted purchases and not get distracted by sale or bargain items that don’t serve you. It’s really fun to plan and research your next purchase and get a couple of high quality items that will last you a long time versus a bunch of cheap things that only last a couple of wears before they start looking beat up.

Perfect Dozen Shirts

Nailing your perfect dozen shirts allows you to have a shirt for every occasion. Your perfect dozen can be a mix of button downs, henleys, polo shirts, and/or t-shirts.

Here’s an example of a perfect dozen I’ve created:

For the average guy, I like to break it up by: 4 button downs, 3 henleys, 2 polo shirts and 3 t-shirts. However, your lifestyle and personal taste dictates how you would distribute your dozen. For example, if you would never wear polo shirts, but love button downs and henleys, go for 5 button downs and 4 henleys.

Why these shirts?


Polo shirts are great for dressing up or down and go well with a range of bottoms from chinos to shorts. When picking out a polo shirt, go for something a little more modern and fun like the burgundy polo I picked with the subtle pocket detail in my example. If you like to keep it simple, go for a soft cotton or cotton-blend unstructured polo (unstructured = loose collar) and avoid the textured sports polos you see everywhere (remember, you’re not playing tennis in this). I went for burgundy and army green because these colors look great both at night and during the day.


Once you do find the perfect t-shirt, grab a couple of colors. You can never go wrong with having a classic black and grey t-shirt. For your third t-shirt, go for a bit of color, in this case I picked deep green. The color you pick can vary on the season you are in. Remember, you can always make a t-shirt look fashionable by wearing it with a pair of boots and fitted jeans, so don’t underestimate the power of a good t-shirt! Make sure you focus on fit and quality.


I love henleys! In case you don’t know what a henley is, it’s a long sleeve t-shirt with a couple of buttons at the top. Think of it as a step up from a t-shirt and a nice change of pace from a button down. They come in a variety of fabrics and styles, letting you dress them up (i.e. cotton-blend fabric with subtle stitching) or keep it casual (i.e. 100% cotton with more obvious stitching). In my example, I went for grey, cream and medium blue. Cream and blue can be dressed up by wearing them with black jeans and brown boots, while the grey would still look casual with the same combo.

Button Downs

It’s always good to have a couple of button downs in your arsenal. When picking out your shirts, go for a range of prints and colors. In this example, I went for plaid, micro-print (blue), a pop of color (red with a white pattern), and a solid one (light grey). Whatever your mood or occasion, you’ll have a button down for it. You can wear these untucked and tucked.

Look at that… your perfect dozen shirts, smart-casual style! Again, you can distribute yours based on what you personally like and where you live. In my example, I picked these because San Francisco has a temperate climate ranging from 50s to high 60s, so muted colors work well here. However, if you live in Florida, long sleeves might not make sense, so you could go for short sleeve button downs and henleys. Also, your color palette might be a bit brighter for hotter environments. Take your time finding the perfect tops. Start with one from each category. Once you find a brand that works for you, see what other styles and colors are available to keep building up. Now that you have your tops, let’s gets your bottoms squared away!

3 Pairs of Jeans

Having 3 pairs of jeans that go with your perfect dozen is the next step. All jeans don’t have to go with all your shirts, but make sure at least two pairs of bottoms go with each top to get the most out of them. For example, all the tops work with dark blue and black jeans, making 24 different outfits. If I were to add in another pair of jeans, I would pick dark grey since they would easily go with all the shirts I picked. Note: the light grey henley works with the grey jeans for a monochromatic look, I would just make sure the shoe breaks up all the grey (i.e. your shoe can be white, brown or even black). Now you have 34 different outfits!

Note: If you live in a warm place and wear shorts, you may want to start with 2 pairs of jeans and 1 pair of shorts.

Note: If you have a harder time finding pants rather than tops, you should start by finding your 3 pairs of bottoms and match the tops to them.

A Pair of Chinos

It’s always nice to have a chino in the mix to switch it up from wearing jeans all the time. With the shirts I picked, I would add in a light chino since it would work with all of my button downs, t-shirts, polos and henleys. Since Spring is around the corner, this light stone chino can take me into Spring and Summer, but still work in Fall and Winter with a darker top.

Again, if you live in a hot environment, you may want to opt for chino shorts.

A Minimal Jacket

Nothing breaks a look like the wrong jacket. I see it all the time, a perfect outfit topped off with a bright orange North Face jacket that doesn’t go with the rest of the outfit. Your jacket doesn’t have to be anything over the top, instead, the more minimal the jacket, the more it’s going to go with. Going for a minimal jacket is not only going to complete all your looks, but gives you a stylish go-to layer you don’t need to think twice about.

With the palette I selected, a navy blue or black jacket will go with all the picks. I went for a collar jacket because it looks great with anything from a t-shirt to a button down and can be worn open to look effortlessly stylish. The style and weight of your jacket will depend on where you live and what your needs are. For example, if it stays cold until the end of Spring where you live, you may want to go for a peacoat or heavier wool jacket. However, if it’s pretty warm where you live and you sometimes need a jacket in the evenings, you can go for something thin like linen.

2 Pairs of Go-To Shoes

For your first two pairs of shoes, I would pick a pair of smart-casual boots and a sleek leather sneaker. Your sneaker will go with all your looks and keep them dressed down, while your boot can dress up even the most simple t-shirt and jeans outfit.

I went for a brown Chukka style boot for this example because brown goes with everything and adds a pop of color to my otherwise muted wardrobe. Alternatively, you can go for a black boot, which will also go with everything, but will keep things subtle. For my sneaker, I would go for black, white or light grey.

To me, a sneaker and running shoe are two different things. Save your running shoes for the gym and keep your sleek leather sneakers for day to day wear. You’ll always catch me saying “sleek leather sneakers”, and when I say that, I am refering to the black example above and the white one below. Your “running shoes” with a giant logo splashed across the side, on the other hand, makes your outfit look amateur. It’s the easiest and most comfortable switch you can make to step up your game.

Alright guys, there you are, your blueprint to master the smart-casual look. What’s awesome about these picks is you have an outfit for each occasion and can make so many different combos. When you are ready to expand your wardrobe further, you can add in sweaters (i.e. zip up sweaters, cardigans etc.) and “nice” sweatshirts (i.e. bomber style sweatshirts, zip up collar sweatshirts etc). Colored bottom are also a great way to expand your collection, for example, you can add in a green or burgundy pair of jeans or chinos to turn it up a notch. Green and burgundy go really well with white, navy blue, grey tops.

Remember, you don’t need to get all these things at once. By spreading out your purchases, you can focus on quality and not quantity. My clients spend a little more on their jeans, but they’ve been wearing them for years on end with no wear in sight. Also, investing in a nice t-shirt or henley ensures they don’t pill or look worn after 5 washes. You can always keep a look out for nice brands in discount stores like Nordstrom Rack or Off Saks 5th to get more bang for your buck. Shop smart my friends!

Still feeling overwhelmed? Check out my new Digital Styling Service where I personally make outfits for you, and once you approve them, you’ll get them shipped right to your door.

Published by

Supreet Chahal

Supreet is from San Francisco, CA. She is passionate about self-growth, healing, music, traveling and fashion. She helps people discover their true and authentic selves through healing and personal style. Check out to get styled or for self care guidance.

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