Updated: June 1, 2020
From basic tees to flannels and polo shirts to henleys, there are a myriad of different types of shirts for men to choose from. Chances are you currently own at least 4 out of the 8 shirt styles that this article is going to cover.
Maybe your closet has all 8 types of shirts. If that’s the case then you’re in luck because in addition to breaking down what to look for in each of the types of shirt, I’m going to show you modern examples of how to wear them, and how they should fit. Plus I’ll highlight a few places you can buy each of the shirt styles.
TYPES OF SHIRTS FOR MEN
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SHIRT STYLE #1: The Undershirt
An undershirt’s main purpose is to act as a barrier between your skin and your shirts, whether that be a dress shirt or a casual button down. They’re a functional piece that helps to absorb your sweat and protect your outer layers.
It’s not always necessary to wear an undershirt as it comes down to personal preference. Me personally, I like to forgo the undershirt in the summer heat, no need for extra layers. But come fall and winter seasons you’ll always find me wearing this type of shirt.
Related: You might like this hands-on guide: Best Undershirts for Men.
I never understood the appeal of wife beaters, besides when I was in middle school and it was cool to rock them. They serve no real purpose, have a bad rep and make you look like you’re wearing a bra. Avoid the wife beater at all costs.
What To Look For In An Undershirt
I suggest a light gray (heather gray) colored undershirt or better yet a color that matches your skin color. If you make the common mistake many men make of wearing a white undershirt with a lighter colored dress shirt, it’ll be visible for all to see.
A color like gray reflects less light and so it will absorb the light whereas white will reflect it. Furthermore, in addition to heather grey, a skin colored undershirt will not be visible as well.
In terms of fabrics, look for words like bamboo, tencel, natural rayon from bamboo, premium combed cotton, jersey, and spandex. As for what type of undershirt to get, opt for a deep v-neck over crewneck.
How To Wear An Undershirt
For starters, don’t make a common mistake and wear a t-shirt as an undershirt. And as the name suggests, undershirts are meant to be worn underneath your shirts and shouldn’t be visible.
That means, as I mentioned above, you want to choose a deep enough v-neck undershirt that will remain hidden, whereas a crewneck will be visible which isn’t the best look IMO, unless of course that’s a look you’re going for. If you’re wearing a necktie, however, then it’s fine to wear a crew neck undershirt.
How An Undershirt Should Fit
Ideally an undershirt should fit more snug than a t-shirt would, fitted being a keyword. You don’t want for it to be restricting to the point you’re struggling to breathe, however an undershirt should hug your body. It should also be long enough to be tucked into your pants without riding back up throughout the day.
SHIRT STYLE #2: The T-Shirt
Ah, the trusty style essential of all essentials, the basic tee. This isn’t the first time I’ve written about the t-shirt and it won’t be the last.
It all started with the plain white t-shirt, which was popularized in the American mainstream when Marlon Brando wore one in the movie “A Streetcar Named Desire.” After that over 180 million were sold and the rest is history.
This shirt style originated as an undershirt, but has long become a style staple for men of all ages and ethnicity. You can find them in every shopping mall and department store with prices varying from under $10 to over $500 which is absurd if you ask me.
What To Look For In A T-Shirt
You can’t go wrong with colors like white, gray, black or navy. 100% cotton is pretty standard for a high quality t-shirt. Bamboo is also a good choice as it has microbial properties. My favorite type of t-shirt to wear is made of pima cotton. I’ve found that shirts with this material can last for hundreds of wash and dry cycles.
If there’s one t-shirt you must own, I’d start with a clean white tee. Matter of fact, pick up several of these shirt styles. Don’t drop several hundred dollars on a basic shirt, though. I’m all for buying quality, but if it doesn’t give you super powers, there’s no need to invest so heavily in a replaceable basic.
How To Wear A White T-Shirt
We wear them to bed, to the gym, with our girls, and the bar with buddies. There isn’t a place where a t-shirt can’t take you except for formal affairs.
Feel free to rock them under a button down shirt, sweater or even a blazer for an ultra-smart casual aesthetic. You can go for more of a street style look by throwing on a bomber jacket with light wash jeans.
In addition to working with light wash denim, t-shirts look great with dark wash jeans, corduroy and chinos just the same. T-shirts even look great worn alone with a pair of slim fit trousers and and clean sneakers or rugged boots.
How A T-Shirt Should Fit
Ideally a t-shirt should be fitted throughout the body, not overly tight or loose. I like for my shirt sleeves to end around mid-bicep and for my biceps to ideally fill up the sleeves for a cleaner aesthetic and to show off the guns of course.
For the length of the t-shirt, you want for it to land just above mid-fly, but not above the belt line. A tip to see if the shoulders fit is to touch the bone at the corner of your shoulder. Specifically, you’ll want for the sleeve stitching to land no more than 1 centimeter from the bone for a proper fit.
Quick note: If you’re enjoying this article on men’s shirt styles, then you might like this guide on Best T-Shirt Brands for Men too.
SHIRT STYLE #3: The Sweatshirt
The sweatshirt is a sporty staple worn by style icons for decades now and continues to endure as a spring or fall wardrobe essential.
As the name suggests, this garment’s counterpart is the athleisure favorite; sweatpants. But I’d say that the sweatshirt is more versatile than sweatpants because a sweatshirt can be worn with more than just athleisure or gym looks as you’ll see below on how to wear a gray sweatshirt.
What To Look For In A Sweatshirt
The ideal sweatshirt in my opinion is a grey crewneck, made out of 100% cotton or a poly-cotton blend, fleece fabric. Another trait of the ideal sweatshirt is ribbed trims along the neckline, cuffs and bottom hem.
How To Wear A Grey Sweatshirt
The following looks featuring the timeless sweatshirt will show that it’s made for more than just athleisure and going to the gym.
The sweatshirt looks great layered. Rock it under a canvas or denim jacket for a stylish spring or fall look. Furthermore, you can pair them with jeans for an off-duty dressed down look or chinos to elevate the sweatshirt a few notches.
Finally you can embrace a casual weekend style by throwing on a pair of white trainers and a sling backpack.
How A Sweatshirt Should Fit
A sweatshirt should either fit snug or more relaxed depending on your preference. A snug fit (seen above) gives off a more refined appearance whereas a relaxed fit leans more casual.
For both the fitted or relaxed look, make sure the neck isn’t at all restricting. The collar should not feel like it’s choking you. A fitted sweatshirt will hug your chest, body and arms, but not appear painted on.
A relaxed sweatshirt can be baggier with longer sleeves and a longer bottom hem. You don’t want it to be too loose or long, however, as that would begin to look sloppy.
SHIRT STYLE #4: The Oxford Cloth Button Down (OCBD)
The oxford cloth button down (OCBD for the style guys) is the quintessential smart casual office shirt that you can easily dress up or down. It’s a dress shirt that’s not as dressy as its name suggests, in fact, it can be quite casual as you’ll see with some of the looks I curated.
Though Brooks Brothers didn’t invent the oxford cloth button down, they made it an pillar of American style. In 1896, John Brooks—who was the grandson of Brooks Brothers’ founder—attended a polo match in England, and noticed that polo players added buttons to their shirt collars to prevent them from flapping in the wind.
He repurposed this for the oxford cloth button down and by the 1920s, the OCBD had become an American classic. It’s one of the most versatile garments you’ll have in your wardrobe, up there with your classic t-shirts, dark wash denim and navy suit.
What To Look For In An OCBD
An clear indicator are holes near the collar tips to latch onto the small buttons, hence the name “button-down.” Contrary to what many think, this is what makes a collared shirt a button down, not just that the shirt has buttons along the front of the shirt.
A white OCBD is essential as well as light blue. Another staple for your closet is the classic Brooks Brothers white button-down shirt with bengal stripes. For fabrics, you’d be hard pressed to find OCBD’s that aren’t 100% cotton. OCBDs are more relaxed in nature (fabric & style wise) than a dress shirt.
It isn’t rare to find an oxford button down shirt with a chest pocket. Since the shirt tends to lean more casual, it’s a common functional detail that you’ll find.
How To Wear A Button Down Shirt
Oxford cloth button downs can be worn with a suit and tie for an ultra-refined aesthetic. I particularly love a good collar roll, which as the name suggests is the ‘roll of the collar’ when it’s buttoned down to the shirt.
Normally you’ll find OCBDs worn more casually whether it’s unbuttoned with rolled up sleeves or worn underneath a sweater or light padded vest.
To elevate an oxford button down, simply add a necktie (silk or knitted), tuck it in, and throw on a navy blazer. To dress down an OCBD, you just gotta wear it with jeans, untucked (sans tie), 2 buttons open or throw a casual jacket over top.
How An Oxford Shirt Should Fit
There are varying types of oxford shirt fits. Depending on your aesthetic, you can pickup everything from a relaxed fit to a slim or trim fit or even skinny/extra trim fit. Different brands have varying descriptions, but just know that oxford shirts can fit you in a multitude of ways.
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SHIRT STYLE #5: The Dress Shirt
If I had to take a guess, every boy and man owns a classic white dress shirt. It’s a cornerstone of a man’s wardrobe that’s worn for all types of events from interviews to cocktail parties, and any other event that requires dressing up.
Sure it may not be the most exciting, but never out of style, this timeless staple has more structure than the aforementioned OCBD. And with a crisp light colored dress shirt comes a myriad of styling options with suits to blazers, and all types of dress shoes which I showcase below.
What To Look For In A Dress Shirt
Start off with a classic, crisp, perfectly tailored white shirt (preferably with mother of pearl buttons) made with fine cotton and high quality construction.
Blue and light pink or light yellow are also great choices to round out your top 3-4 dress shirts in your closet. If you don’t want to deal with the hassle of ironing your shirts daily, look for “wrinkle free” or “non-iron.” Though through my experience, chances are you’ll still have to iron since these labels just mean that the shirts are less prone to wrinkles.
There are an endless array of collar options when it comes to dress shirts from point collars to tabbed, pinned to button-downs or spread collars. Each have their own unique characteristics that will accentuate or work against your face shape.
A quick rule of thumb for collars and face shapes: If your face is more round go for a point collar and if it’s more narrow, go for a spread collar. You can also completely disregard this as I normally do. It’s your personal style after all.
How To Wear A Dress Shirt
The dress shirt is every bit as its name implies, meant to be worn dressed up. A key getup featuring the dress shirt is fully suited up, collar closed with a necktie. Want to dial down the formality? Simply lose the tie and unbutton the top two buttons for a more carefree, still refined ensemble.
Just as you can wear a dress shirt with a solid suit, you can wear them with a blazer and odd trousers. For blazers, I like to stick with the classics—navy, tan, gray or even olive.
How A Dress Shirt Should Fit
Similar to the oxford shirt, the dress shirt comes in varying fits from more relaxed to slim fit. The more modern and cleaner look is the slim fit shirt, tucked in without any billowing at the waist.
Just like any other shirt you’ll want for your dress shirt’s shoulder seam to hit right where the bone is for a comfortable fit. Higher arm holes mean a better more contemporary fit. The collar shouldn’t be too tight, there should be enough room to slide two fingers inside with the top button buttoned.
As for the sleeves, there should be clean lines and not too much extra fabric. Anytime you’re drowning in fabric it’ll always look sloppy. For the sleeve length, you want for the cuff to hit at the tiny divot that divides your hand and your wrist.
When you start getting an eye for good style you’ll be able to tell a proper fitting t-shirt from an ill-fitting one in an instant.
SHIRT STYLE #6: The Polo Shirt
Polos are divisive for some men, but men of style know that the polo shirt is a classic style staple not to be ignored. It’s distinguished by a 2-4 button closure and a soft collar.
The polo shirt we know and love today can be traced back to 1926 when legendary tennis star Jean René Lacoste wore a white polo shirt in a match, which made him an outlier among players wearing a more formal dress shirt with rolled sleeves.
He earned the nickname Le Crocodile because of his on-court tenacity, quite fitting for the Lacoste brand, famous for its crocodile icon.
The other iconic brand that springs to mind when it comes to polos is Ralph Lauren, the company who basically owns the category name. Ralph Lauren’s polos are classic American style. They were a relatively late-comer to the market, made 33 years after Lacoste, but both have become household names.
For decades now, the polo shirt comprised golfers’ and tennis players’ uniform because of performance fabrics which easily wicks away sweat and allows athletes a wide range of motion.
Fun fact: The polo originated as a button-down collared shirt. Today you’ll find these shirt types sans button-down collar.
On the topic of polos, check out this long-term review of the Banana Republic Luxury Touch Polo.
What To Look For In A Polo Shirt
For the sake of simplicity I’m going to omit performance polos intended for athletes and focus on everyday polo shirts.
The most common type of polo shirt you will find is made of pure cotton with breathability, comfort and durability in mind. If the length of the polo is shorter (landing just below the belt line) then it’s meant to be worn untucked.
If there’s a longer tail that covers your bottom, then the polo is meant to be worn tucked in. Avoid wearing a polo shirt with a longer tail untucked, it’s not a good look, in my opinion.
As for textures, pique polos have a pique knit that lean more casual while a luxury-touch cotton fabric with a smoother, jersey weave gives hints of a more refined look.
How To Wear A Polo Shirt
Polos aren’t just for preppy guys. The polo shirt is a summer essential that more guys should embrace. It’s more elevated than a basic t-shirt and more casual than a dress shirt. Though the original polo was white, polos come in a myriad of color options to rival that of a rainbow.
One of my favorite ways to wear a polo shirt in the summer is tucked in with white trousers, loafers and a matching belt. It’s a casual cool look that’s easy to pull off with a little bit of confidence. It’s a standout look without standing out.
Alternatively you could pair your polo shirt with a casual suit or a light, unstructured blazer with odd trousers and white trainers. It’s a super smart look that will have the ladies callin’ you sharp, stud.
To pop the collar or not? I’d say leave the popped collars for teens and frat bros who are trying hard to be trendy. However, there is a time when a popped collar is appropriate. If you’re on vacation in the summer heat with the sun blazing, then a popped collar can help to protect your neck from the elements.
How A Polo Shirt Should Fit
The way I like for my polos to fit are similar to my t-shirts, fitted through the body, and not skin tight. The collar should be able to close completely without feeling restricting around your neck.
A good length for a polo shirt is just above mid-fly, similar to the fit of a basic tee. For the sleeves, I like for my biceps to fill up shirt sleeves or if not, then to still have a fitted aesthetic.
If it’s too loose around the arms it begins to look sloppy. For the sleeve length, it should end around mid-bicep for a more modern appeal.
SHIRT STYLE #7: The Flannel Shirt
Flannel and fall go hand in hand. These types of shirt are perhaps my favorite fabric to wear when the weather begins to dip. Something about the soft, smooth feel that is ultra comfortable and warms you right up.
A hallmark of the flannel shirt is the variety of patterns and colors you’ll find them in. They’re almost always comprised of earth tones, from burnt orange to red plaid to mustard yellow, green, navy and brown.
What To Look For In A Flannel Shirt
Look for 100% cotton or 100% combed cotton with a twill weave. As for the fabric weight, that depends on how thick you prefer your flannel shirts to be. Keep in mind that one-ply will be thinner than two-ply and the higher the g/m2 and the higher the yarn count the thicker the fabric.
Every guy who owns a flannel shirt probably has a one in a plaid pattern. Opt for a solid flannel or gingham check for something a little different.
How To Wear A Flannel Shirt
There are many stylish ways to wear a flannel shirt. For a smart and stylish look, you can tuck in the flannel shirt, throw on dark brown suede jacket with sunglasses and tailored dad jeans.
For a more elevated look, you can play with layering and put on a turtleneck sweater as the base and a sharp blazer with a pocket square to finish it off. Not too shabby for a flannel style.
Since the flannel shirt is a decidedly casual, and stylish layering piece, perhaps the simplest way to wear it unbuttoned overtop of a well fitting t-shirt with mid or dark wash slim fit jeans.
Flannel’s rugged aesthetic also makes it an ideal pairing with everything from chukka boots to work boots.
Quick tip: Feelin’ like a rebel? Wrap the flannel shirt around your waist and rock a leather jacket with dark wash jeans and work boots.
How A Flannel Shirt Should Fit
I personally like my flannels to fit looser than my button downs and dress shirts. A looser fit makes you better equipped for layering.
Even though I prefer a looser aesthetic, the core principle of proper fit is still in play. The shirt shouldn’t be too long nor too baggy, just a little bit looser and longer than your regular button downs and you’ll be fine.
SHIRT STYLE #8: The Henley
The last type of shirt on this list is the popular henley. Basically a henley shirt is a collarless pull over that’s characterized by a placket beneath a round neckline.
Typically you’ll find anywhere from 2-5 buttons and they come in short or long sleeves. It stands out from your basic tees and is more casual than the polo shirt.
Unlike the rest of the shirt styles on this list, henleys aren’t for all men. They’re best suited for men with muscular builds and bigger chests. Henley shirts looks great on men with a built physique, but can be pretty unflattering on skinny guys.
According to Wiki, henley shirts were named because it was the traditional uniform of rowers in the English town of Henley-on-Thames way back in 1893.
What To Look For In A Henley
I feel like I’m repeating myself over and over, but you’ll want to look for 100% cotton here just like the rest of the shirts on this list.
A henley in white or beige, navy or grey is an excellent choice. You can also find henleys with a waffle knit similar to thermal shirts. These textured henleys are great for layering underneath a button down or flannel shirt.
How To Wear A Henley
The short sleeve henley will mostly be worn in the warmer months of summer.
Feel free to wear them casually with shorts or dress them up with a pair of fitted khakis, leather belt and brown loafers. Alternatively you can throw on a printed short sleeve button down for a carefree casual attitude.
As the weather cools, you’ll want to opt for a long sleeved henley shirt. It looks great layered under a plaid shirt, light vest or thick shawl collar cardigan.
One of the cleaner looks is pairing an all white long sleeved henley with grey check trousers and matching jacket. It’s an ultra-refined look that looks great with a smile. Even better if you’re Michael B. Jordan (see gallery above).
How A Henley Should Fit
A henley should be fitted to one’s body as that’s the most flattering fit. In this case, tighter can be better. Just look at The Rock rocking a henley, the dude is a monster.
The length of the shirt can be a bit longer than your regular t-shirt or polo shirt. Henley’s are inherently casual and so the long line aesthetic doesn’t look half bad.
You made it through over 4,000 words all about men’s shirt styles. Congratulations is in order. Thanks for reading all the way through and I hope you got some value out of this article, particularly on how to style the various types of shirts. And I also hope you enjoyed reading as much as I enjoyed writing this article.
This post was originally published September 20, 2018. It has since been updated with additional information and updated brands.
WHICH OF THESE TYPES OF SHIRTS ARE IN YOUR CLOSET?
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