5 Types of T-Shirts & How to Wear Them

You are now reading Gentleman Within’s definitive t-shirt guide. Today a t-shirt can be found in every man’s wardrobe. Along with underwear and socks, it’s without a doubt the most commonly worn article of clothing.

We wear them under dress shirts, jackets, and blazers, from our bedside to the beach, we even wear them to sleep. In fact, you’re probably wearing one right now.

So why are t-shirts even worth talking about — I mean it’s just a shirt, not much to say right? Au contraire, this simple yet versatile men’s wardrobe essential has history, and there’s a reason why it’s worn by everybody from rockstar celebrities to your average joe.

In this definitive t-shirt guide I’ll go over 5 different types of t-shirts, ways to wear them, how a t-shirt should fit, and where to buy them.

5 t-shirt types we’ll be styling in this definitive t-shirt guide.

But first, per usual, let us begin with a quick history.


Marlon Brando in A Streetcar Named Desire | GENTLEMAN WITHIN
Marlon Brando made the basic white tee cool to wear on its own

As with other menswear staples, the plain white tee dates back over a century ago. And like other articles of clothing, the t-shirt has its history in the U.S. military.

Today’s classic t-shirt has origins as an undergarment. Around the late 1800s, it evolved from a one-piece (no, not the trending dude romper) called the union suit. Then in the early 1900s, the U.S. Navy began issuing t-shirts as undergarments. And after World War II, veterans began wearing t-shirts as everyday casual clothing.

We can also thank Hollywood for the popularization of the plain white tee. In the 1950s, after Marlon Brando wore one in A Streetcar Named Desire, the t-shirt became fashionable to wear on its own.

Today the basic t-shirt is a foundational piece in a man’s wardrobe. Along with dark wash denim and the navy blue blazer, the t-shirt rounds out my top 3 men’s style essentials.

Best Breathable Summer Fabrics to Keep You Cool (Men's Style Guide)» Related: You might like this definitive guide to Summer Fabrics.


T-shirts are so ubiquitous that they’re often overlooked. That’s why I wanted to style 5 different types in this t-shirt guide to show just how stylish and versatile they can be.

1. THE CREW NECKStandard Crewneck T-Shirt

The crew neck t-shirt is defined by the rounded, circular neckline. It’s the most common t-shirt type and worn by everyone. They’re most suitable for men with long or narrow faces and sloped shoulders. Reason being that a round collar helps to create balance with a narrow face, and they create an illusion of rounder shoulders so that you appear broader.

Scenario 1: Crewneck & Denim

Ah, the classic crewneck. Worn stylishly by guys like James Dean, David Beckham, Johnny Depp, and Adam Levine—the crewneck is the one. It’s probably seen some of your worst and best days.

Since the t-shirt leans highly casual, I paired the crewneck with denim and chambray, both casual fabric types. The white tee looks particularly great layered underneath denim and blues. The casual white sneakers with a rubber gum sole add to the overall casual nature of these looks.

Finally, I added the brown, tortoiseshell sunglasses for a devil may care nonchalance.

Crewneck t-shirt and denim outfits | GENTLEMAN WITHIN
SHOP THESE LOOKS — T-Shirt: UNIQLO | Button-Down Shirt: J.Crew | Denim Jacket: Levi’s | Pants: Everlane | Shoes: Nike | Watch: Casio | Sunglasses: Warby Parker


The second shirt in Gentleman Within’s definitive t-shirt guide is the v-neck. The v-neck’s purpose is so that the fabric of the shirt is not visible while wearing a shirt over top. Though it’s common for men to wear crewnecks under an unbuttoned shirt, I think it’s a distraction to see any type of visible fabric underneath. Which is why I always prefer v-necks under an unbuttoned dress shirt, or no shirt at all.

V-necks are flattering on men with more round faces and a larger upper body. Shorter men can also benefit from a v-neck because it naturally elongates the neck, which creates the illusion of length or height. It also helps to create a slimming effect for larger men.

Scenario 2: V-Neck & Jacket

If you’ve seen Pulp Fiction, then you know Bruce Willis’ character rocks a suede bomber jacket over a white crewneck. I decided to emulate the look with a twist, opting for the v-neck instead of the classic crew. It’s just slightly edgier. Same goes for the v-neck under a blazer.

Since navy and brown are a classic color pairing, I went all brown and blue with pops of white from the shirt and shoes. I also liked how the brown and blue accent colors from the shoes is mirrored by the navy chinos and brown jackets.

If you think the jackets are too dressy for this look, remember that a tan blazer with patch pockets is inherently casual, and a brown suede bomber is the perfect jacket to dress up or down. In this case, both looks are casual and dressy at the same time.

V-neck t-shirt with blazer and bomber outfits | GENTLEMAN WITHIN
SHOP THESE LOOKS — T-Shirt: Hanes | Tan Blazer (similar): Amazon Fashion | Bomber Jacket: Barneys Originals | Chinos: Uniqlo | Shoes: Nike | Watch: Casio

8 Best Undershirts for Men that Stay Tucked In 2020 (Tested & Compared) | GENTLEMAN WITHINQuick note: If you’re enjoying this definitive t-shirt guide then you might like this article on the Best Undershirts for Men too.

3. THE HENLEY (Y-NECK)Henley T-Shirt

Henleys are perfect for guys with well defined chests. Muscular men look really good in them. It’s like a crewneck, v-neck hybrid that just works. The henley not only accentuates the muscular build, but it’s masculine in its aesthetic, plus it’s more stylish than the basic crewneck or v-neck.

Want some styling inspiration on how good a henley can look on the right kind of body type, check out this Pinterest gallery.

Scenario 3: Henley & Vest

This short sleeved henley fits flawlessly. Though I must admit, I haven’t seen a gym in the past 8 months, something I’m looking to correct soon. A few more chest days (wishful thinking) and I’ll actually be able to create the now elusive y-neck.

To me, henleys lean more rugged and that’s why I thought a pair of burnished brown leather boots would help to ground the look. And since it’s warming up, I’m all for lighter wash jeans as much as I love dark wash denim.

To make for an even more rugged aesthetic, I pulled out the light vest. It’s stylish, functional and easy to store. Finally, if you know me, I love accessories, especially during the warmer seasons where they can make for the ultimate statement pieces, hence the leather watch and bracelet.

Henley (y-neck) and vest outfits | GENTLEMAN WITHIN
SHOP THESE LOOKS — T-Shirt: Banana Republic | Vest: Uniqlo | Jeans: Levi’s | Boots: Thursday | Watch: Timex | Watch Strap: Cheapest Nato Straps (use GentlemanWithin15 – 15% off your order)

4. THE SCOOP NECKScoopneck T-Shirt

The scoop neck isn’t an essential in the world of t-shirts. Not many men wear them because they’re a bit tricky in knowing what to pair them with. This shirt is defined by the extra wide neckline.

It looks good on men with a well-defined chest. It’s also best worn looser fitting as the fabric tend to be lighter and free flowing, which makes it perfect for spring/summer seasons.

Put it on and you’ll (maybe) look like Ryan Gosling, who’s clearly mastered the art of the scoop neck.

Scenario 4: Scoop Neck & Washes

I’ve never worn a scoop neck t-shirt until now. I’ve always heard about Ribbed Tee (out of stock) and the hype surrounding their shirts. I like the relaxed nature of this slub cotton scoop neck, especially with the pocket detail.

It’s light and airy, a bit long, but I can shorten it. The long line tee is a thing in streetwear circles, and in all honesty with the scoop neck, the length doesn’t bother me that much.

To me Chelseas are the one pair of boots you can wear year round. I love how this particular pair from Thursday Boots plays harmoniously with light and dark wash denim. Chelsea’s rock because they’re versatile and can straddle the fence between casual and dressy.

Finally, I threw on the Timex Weekender and brown leather bracelet to finish off the look in a stylish way.

Scoopneck t-shirt light wash & dark wash with chelseas outfits | GENTLEMAN WITHIN
SHOP THESE LOOKS — T-Shirt: Amazon | Light Wash Jeans: Levi’s | Dark Wash Denim: Banana Republic | Boots: Thursday | Watch: Timex | Watch Strap: Cheapest Nato Straps (use GentlemanWithin15 – 15% off your order)


We round out this t-shirt guide with the polarizing graphic t-shirt. The ever trendy graphic tee is characterized by graphics in the form of photographs or typography, usually on the front of the shirt.

The graphic tee gets a lot of flack from the menswear community, but they’re not all that terrible. The key with graphic tees is to stay away from blatant advertising or cheesy phrases, eg. those shirts from Abercrombie and Hollister back in the 2000s (are they still doing this?)

The key with good graphic tees is subtlety. Keep the graphic clean, minimalist or almost invisible. Rock it on it’s own without layering anything overtop, and let the graphic shine.

Scenario 5: Graphic Tee & White Out

I wanted to keep it really simple with this graphic tee look. This has been one of my favorite graphic tees of all-time. I’ve literally worn it hundreds of times over the past 8 years. It’s made of pima cotton, if you don’t know, this fabric feels luxurious and is super durable.

You’ll notice how subtle the graphic is. This is how I like to rock graphic tees these days. Minimal, but still visually interesting. I thought the white jeans paired well with the green, the minimalist Casio (super value, only $10) watch, and casual sneakers.

Rocking a graphic tee | GENTLEMAN WITHIN
SHOP THIS LOOK—T-Shirt: Armani Exchange | Jeans: Levi’s | Watch: Casio | Shoes: Nike

Quick note: If you’re enjoying this definitive guide to the t-shirt, then you’ll probably find my other writing on all things men’s style useful. Each week, I share updates, style tips and other things not shared on the blog through my free email newsletter.

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With the t-shirt fit, it’s quite simple. Make sure that it fits well, fitted being the keyword. Not painted on, not baggy, but fitted. The neckline shouldn’t be choking you, and the fabric should not be restricting on your body because that’s more of how an undershirt should fit.

Remember, fitted with flowing fabric is okay, but not overly loose where you’re drowning in the sleeves, chest or stomach area. Here’s a great 1 minute demonstration by The Idle Man on how a t-shirt should fit.


Anywhere, really. Virtually every single brand known to mankind sells their own version of the classic white t-shirt. But since this is the definitive guide to t-shirts, I researched some well-rated brands that also come recommended by my colleagues, as well as some based on my own experience that won’t have you breaking the bank.

And whatever you do, please don’t go dropping $350 on any white tee. Ever. No matter what brand it is.

Best T-Shirt Brands For Men | GENTLEMAN WITHIN» Related: You might like this hands-on review of the Best T-Shirts for Men.



Armani Exchange | Pima Crew
UNIQLO | Supima® Cotton Crewneck
UNIQLO | Supima® Cotton V-Neck
J. Crew | Slim Broken-In T-Shirt
Express | Flex Stretch Textured V-Neck Tee

A couple final pieces of advice.

As with any articles of clothing, try the t-shirt on in a store if you can, and see if it fits well. When you’ve found a place that has your perfect fit, that can be your new go-to.

And if you’re going for 100% cotton and can afford a premium, look out for Pima or Egyptian cottons, which are made from long staple fibers that last longer, look thinner and feel lighter.


Like the navy blazer and dark wash denim, the classic t-shirt is undoubtedly a menswear staple. In this article, we covered 5 different types of t-shirts, several different ways to wear them, how they should fit and where to buy them.

See, there is much to discuss when it comes to the basic t-shirt, after all.

Not sick of shirts yet? Here’s an in-depth ultimate guide on 8 shirt styles for men. And if you liked reading this definitive t-shirt guide, you can check out the other articles in the Essential Men’s Style Series.

Essential Men's Styles: 5 Types of T-Shirts & How to Wear Them with Style | GENTLEMAN WITHIN


Let’s continue the discussion over in the Gentlemen Within Private Facebook Community.

Looking forward to seeing you in there.



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Khoi Nguyen

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