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 reasonwhy 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.

AN ABRIDGED HISTORY OF THE T-SHIRT

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 denimand the navy blue blazer, the t-shirt rounds out my top 3 men’s style essentials.

1. THE CREW NECK
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.

2. THE V-NECK

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 rounder 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 jacketover 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.

3. THE HENLEY (Y-NECK)

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.

4. THE SCOOP NECK

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 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.

5. THE GRAPHIC T-SHIRT

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.

Thanks for taking the time to read this post. We’d love to hear from you! Please leave a comment below and let us know your experiences with t-shirt design software.

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