Hey guys, let’s chat about how to wear a suit the modern way. If you’re wearing baggy suits with boring basic dress shirts and plain ol’ dress shoes, you’ve come to the right place. Nowadays, the modern guy gets noticed when he wears his suit differently from the rest of the crowd. In this post, I’m going to not only show how to wear a suit the modern way, but also make sure you feel confident doing it.

In this post we’ll chat about dress shirt alternatives, how your suit should fit and your shoe game. 

Note: this advice is for places where you can get creative with your outfits (think weddings, parties etc.). If the event is super formal, stick to the classics like a dress shirt and dress shoes, but you can still have fun with print.

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T-Shirt and a Suit

So you’ve probably seen guys rocking t-shirts with a suit, but feel like you can’t pull it off for the life of you. Don’t worry, I have you covered. There’s a technique to wearing a suit with a t-shirt and it has to do with the type of t-shirt and how to style it. 

Stick to t-shirts for more smart casual settings since they give off a relaxed and dressy vibe.

Source: Pinterst

Outfit Breakdown: Chambray Suit + Navy T-Shirt + Loafers

For a very casual look, sneakers look great!

Source: Pinterest

Outfit Breakdown: Casual Grey Suit + White Tee + White Dressy Sneakers

Make sure your suit fits well. A couple of things to keep in mind are…

  1. The length of the jacket should be shorter than a “traditional” suit. About an inch or two from your the bottom of your zipper should do the trick.
  2. Don’t have more than one break in your pants. Even going for an ankle length pant is okay with no show socks
  3. Slimmer jackets and pants look more put together

Source: Pinterest

Outfit Breakdown: Blue Suit + Black T-shirt + Brown Derby Shoes

Your T-Shirt Doesn’t Have To Be White

White t-shirts aren’t for everyone and they make the suit look more casual, however, wearing a darker colored t-shirt makes it look dressier. Also, have fun with color in your suit too. Adding a pop in your shoes can help break up dark colors.

Source: Pinterest

Outfit Breakdown: Casual Burgundy Suit + Black Tee + White Converse Sneakers

If you need to make it dressier, your shoe choice can help you achieve that. Go for boots, derby or oxfords, loafers or a classic dress shoe.

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Outfit Breakdown: Blue Suit + Striped Tee + Brown Derby Shoes

Since a t-shirt and suit look can be a bit tricker to pull off, here are some do’s and donts that make it easier.

T-Shirt and Suit Dos and Don’ts:

Do: Tuck in your t-shirt for a cleaner took
Do: Watch the length of your untucked t-shirt (don’t go too long, see photos for reference)
Do: Wear dressy sneakers
Do: Wear a crew neck t-shirt
Do: Wear a fitted suit
Do: Go for non-white t-shirt if white doesn’t look good on you (a darker t-shirt will look dressier)

Don’t: Wear an old ratty t-shirt
Don’t: Wear a t-shirt too loose
Don’t: Wear a overly fancy suit with a t-shirt 
Don’t: Go too dressy in the shoe

What Not To Do…

The outfit below is a bit of a miss because the suit is too dressy to wear with a t-shirt. The material of the suit and shoes makes the outfit look formal, however, the casual t-shirt kind of throws off the look. When going for suit styles, go for a cotton or texture, rather than a fancy Italian wool suit.

Source: Splash News

V neck t-shirts look so-so with a suit, so wear them with caution. Go for a crew neck or a scoop neck (scoop neck: a crew neck that doesn’t sit so high).

Source: He Spoke Style

Polo Shirt and a Suit

T-shirt feeling too casual or not doing it for you? Try a polo shirt! Polo shirts are still casual, but more dressy than a t-shirt. The collar on a polo shirt looks great. When I say polo, I don’t mean your bright thick cotton polo shirt.

With polos, you can wear them tucked or untucked, just watch the length when untucked. Also, you can button up all the buttons or leave the top one unbuttoned, both options look great.

Watch the fabric of your polo shirt, you don’t want to wear a thick cotton causal looking polo shirt, instead you want something smoother, sleeker and thinner. 

Since your polo shirt is dressier than a t-shirt, you can wear dressier shoes with this look.

Source: Pinterest

Outfit Breakdown: Grey Suit + Black Polo Shirt + Black Monkstrap Shoes

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Outfit Breakdown: White/Grey Striped Seersucker Suit + Red Polo + White Sneakers

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Outfit Breakdown: Charcoal Suit+ Black Polo

Henley and a Suit

If polo shirts aren’t your thing and t-shirts feel too plain, try a henley. Henleys are short or long sleeved t-shirts with buttons going down the front. You’ll be surprised how big of a difference those buttons can make. 

Henley shirts fall between a t-shirt and polo, so you can choose to dress them up or down. However, keep in mind that a henley is a type of t-shirt, so avoid going too formal in your overall look. 

Source: Pinterest

Outfit Breakdown: Grey Suit + Striped Henley + White Sneakers

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Outfit Breakdown: Blue Suit + Navy Henley + White Sneakers

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Outfit Breakdown: Tan Suit Jacket + Brown Slacks + Cream Henley + Brown Loafers

Turtle or Mock Neck with a Suit

As the weather gets colder, consider a turtleneck or mock neck. A mock neck is basically a turtle neck, but with no fold. I personally love mock necks and find they aren’t so suffocating, especially if turtlenecks feel too much for some people around the neck. 

Your turtle or mock neck acts dressier than any of the shirt styles I listed above, so feel free to dress it up or down according to your liking. 


Source: Pinterest

Outfit Breakdown: Brown Suit + Brown Mock Neck


Source: He Spoke Style

Outfit Breakdown: Brown Plaid Jacket + Tan Turtle Neck Sweater + Grey Pants


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Outfit Breakdown: Grey Suit + Grey Cable knit Turtle Neck Sweater

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Outfit Breakdown: Blue Suit + Copper Turtle Neck Sweater + Black Dress Shoes

When wearing a t-shirt, polo or henley with a suit, here are some things to consider:

  1. Make sure the material of the t-shirt, henley or polo shirt looks soft and smooth. I don’t want you to wear your old pilled t-shirt with your suit, it will completely throw off the look.  
  2. Consider a loose tuck if you’re unsure whether to tuck or untuck your top. A loose tuck is when the shirt isn’t fully tucked in, but looks intentional and clean. 
  3. Depending on the occasion, go for a pair of dressy sneakers, it can make your outfit look fluid and complete. Going for no show socks is also a great option. 
  4. Consider the length of pants. For example, ankle cut pants looks better with the no show socks and is much more modern. 

Printed Shirt

The thought of wearing a suit without a dress shirt freaking you out? It’s all good. You can make your outfit look modern by pairing it with a printed dress shirt. You can go for small geometric prints or something fun like floral.

Source: He Spoke Style

Outfit Breakdown: Tan Suit + Printed Button Down + White Sneakers

Source: Pinterest

Outfit Breakdown: Blue Suit + Printed Dress Shirt + White Sneakers

Source: Pinterest

Outfit Breakdown: Blue Suit + Printed Dress Shirt + Brown Derby Shoes

Your Modern Shirt Shoe Game

To complete your modern look, let’s chat about shoes. You have a couple options for shoes and they will depend on the top you pick. 


When wearing any of the tops I listed above, clean dressy sneakers work really well. When wearing sneakers, make sure you do the no show sock look because it looks sleek and intentional. Show a bit of ankle to keep up with the casual vibe of the look. Ankle pants work really well in Spring, Summer and early Fall.

Source: Pinterest


Loafers totally work for the tops as well. Loafers are dressier than sneakers, but depending on the style, can still be considered casual. You don’t wear socks with loafers, so they are better in non-winter weather. 

Source: Pinterest

Outfit Breakdown: Blue Suit + Striped Polo + Brown Loafers

Dress Shoes

You can totally rock dress shoes with the tops if you like formal footwear better. Feel free to have fun with your dress shoes and don’t feel like you have to go for something so serious. Going for a light brown or grey color helps break up the seriousness of black. Dress shoes work all year round too.

Source: He Spoke Style

Outfit Breakdown: Brown Suit + Black Turtleneck + Dark Brown Dress Shoes


As the weather cools down, boots are a great option to wear with your modern suit. Wear your pants over your boots. Going for a boot with a bit of wing-tip or something fun can help elevate your look. If you want to learn more about boots, check out The Ultimate Guide to Boots.

Source: GQ

Outfit Breakdown: Blue Suit + Black Tee + Brown Boots

Additional Tips

Go for color! You don’t need to wear a solid black or blue suit, instead, try colors like green, burgundy or even plaid. This is your opportunity to stand out in the sea of black suits, so take it. Don’t know what color looks good on you? Make sure to get the Ultimate Guide to Your Best Colors to see what colors work with your unique skin, hair and eye color. 

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Outfit Breakdown: Burgundy Suit + Black Turtle Neck

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Outfit Breakdown: Green Suit + White Tee + White Sneakers

Modern suits are cut higher than your traditional suits. Take a look at the men in the photos to see where their suits hit. You will notice they run shorter than traditional suits and it looks so much better. 

Source: Pinterest

Outfit Breakdown: Blue Suit + Black Polo + Black Dress Shoes

Ankle pants or rolling up your pants looks great with a modern suit. This style looks great in non-winter settings, so make sure you consider the weather before trying this look. The example below shows the perfect amount of ankle to show if you want to try this look.

Source: Pinterest

Consider pairing chinos with a sports coat to achieve a suit look. This is a great opportunity to pair a plaid jacket with solid colored chinos. You can mix and match this look to create multiple outfits. Tip: Go for dressy looking chinos. 

Source: Pinterest

Outfit Breakdown: Grey Blazer + Copper Turtle Neck + Burgundy Pants

Alright guys, there you have… your guide to wearing a suit the modern way! My biggest tips is to have fun and try things. You can always ask a friend to do a fit check to make sure your look works. The world of modern men’s suit is taking a turn to be more comfortable and casual without sacrificing style. The smallest step you can take is to see what photos resonate with you and that can help you narrow down which look you want to go for. The step after that is to try things on.

Until next time…

The stylist in your pocket,


PS. What if there was a step by step video course that walked you through the exact style consulting process I take all my clients through? Would you be interested? I’m cooking up something pretty neat to help you not only establish your personal style, but bring it to life. Check out The Style Game Plan for more information. If you are on my email list, you will be hearing more about, so don’t forget to sign up.

Supreet Chahal

Supreet is a Fashion Stylist from San Francisco, CA. She helps both men and women establish a sense of style and dress with confidence. If you want to work 1:1 with Supreet, visit StyleBySupreet.com. If you're a guy looking to learn more about style, check out PocketStylist.io, a site dedicated to teaching men how to dress well.

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