Everything You Need to Know About Men's Underwear

Underwear is often the most neglected aspect of a man’s wardrobe. We tend to keep underwear in rotation for far too long, usually until they’re so worn out that they physically can’t be worn any longer. Besides, what’s a few tears or stains in the face of true comfort?

It usually takes a shaming from a partner to ditch our most well-worn pairs, but stocking up on underwear isn’t as simple a task as it used to be. While you can find underwear at any pharmacy these days (or even a gas station if you’re really desperate), there are more options than ever, from the traditional briefs we all sported as kids (read our picks for the best briefs here), the boxers we rocked as teens (read our guide to the best boxers here), and the increasingly popular boxer briefs and trunks.

Read on for an overview of the most popular styles of men’s underwear to help guide you on your next shopping trip. Whichever style you choose, you want to be ruthless when it comes to your older pairs. Embrace your inner Marie Kondo and get rid of those rapidly-decaying old underwear for good.

A Little History...

While we’re not going to dive too deep into the origins of undergarments (that’s what Wikipedia is for), it’s helpful to understand how and why male underwear has evolved over time.

Skipping forward a few thousand years from the extremely revealing loincloth, the classic briefs as we know them were first sold in North America in 1935 by Coopers, Inc. They were billed as “The Jockey,” since they were designed to mimic the supportive jock strap used by athletes. As opposed to the body-length undergarments that had preceded it, the jockey had a form-fitting style that quickly caught on, making it by far the most popular men’s undergarment for decades.

The reign of the mighty briefs nearly came to an end in the ‘90s with the emergence and immediate popularity of boxer shorts. Covering most of the thigh and with a looser fit, boxers were a drastic change from briefs, and benefited the style of the times, which favored baggier clothing (this was the era when parachute-sized JNCO’s ruled the streets). It’s long been thought that boxers first originated from designer John Varvatos while he was working for Calvin Klein in the ‘90s, which made boxers a must-have for every man’s wardrobe thanks to their wildly popular “Marky Mark” [Wahlberg] ads from the era.

As fashion moved away from baggy clothing to more form-fitting styles (just try to buy something not listed as “slim-fit” these days), the popularity of boxers has been supplanted by boxer briefs and trunks, each offering a snug fit that won’t get bunched up by today’s slim-fitting jeans.

The Styles

Cartoon of Men's Underwear


Often derided as “tighty-whiteys,” briefs rarely get a fair shake. Let’s face it – it’s hard to get excited about underwear that reminds you of being a toddler. Yet there’s a reason why briefs are still so popular, regardless of age – they simply offer better support than any other men’s underwear on the market.

With their Y-shaped design, briefs hold everything snugly in place, providing the ultimate in support. While some may prefer letting their boys hang free, it’s hard to beat the comfort of a pair of properly-fitting briefs. Securing the right fit is essential for briefs – they’re meant to be snug but not too tight. While the old rumor about tight briefs lowering your sperm count has been endlessly debated, you don’t want to smother that area – it’s worth trying a couple of sizes to be sure you have the best fit possible.  

Briefs are also best for working out and playing high-intensity sports – wearing boxers during an intense workout or game can result in chafing, or even worse twisting mishaps (look up “testicular torsion” if you want to ensure a sleepless night).

Briefs are now available in a variety of materials and lengths, including low, mid- and high-rise cuts, so you don’t necessarily have to sport the same style you did as a kid (not that there’s anything wrong with that).


By far the most popular underwear choice for men, boxer shorts offer a great balance between comfort and style. By letting everything hang free, boxers feel like you’re going commando, while still protecting your area from needless friction from pants and shorts. They also provide much better air-flow than briefs, which helps keep you cool and dry. By extending partway down your leg, boxers are essentially like wearing a thin pair of shorts all day. There’s also the convenient fly opening so you don’t have to pull your underwear down like a child whenever you need to hit the john.

Boxers are available in a huge array of styles and lengths these days, with many more form-fitting options than in the past. The styles of yore were often excessively large and bulky, which made sense when everyone was rocking oversize carpenter jeans, but today’s slimmer pants styles call for a much thinner style of underwear.

Boxer shorts are also the best choice for lounging around the house on a day off or chilling in the morning. For bonus points, your partner can also wear them too – you don’t see people borrowing their partner’s briefs while making breakfast.

Boxer Briefs

Boxer briefs, as one might expect from the name, offer a great middle-ground between classic briefs and boxer shorts. They provide the comfort of briefs with the style of boxers, making these some of the best-looking underwear options for men on the market.

Unlike traditional boxers, boxer briefs have a much shorter leg, reducing the chance they will bunch up under your pants. However, unlike boxers, they won’t leave you hanging – boxer briefs provide the same support as briefs, keeping everything snug and in place, but in a much more attractive package.

Along with trunks (more on that below), boxer briefs are one of the most stylish underwear choices for men today. You will appreciate the form-fitting look, and you won’t have to sacrifice any of the comfort of traditional briefs.


Residing somewhere between the extended leg length found in boxers and the close-fit of briefs lies the underrated trunk, a fashionable and form-fitting variety of underwear that offers the best of both worlds. The inseam of a pair of trunks is generally half that of a pair of boxers and offers a snugger fit, allowing you to show off those thigh gains.

Trunks are also the best choice if you’re rocking a pair of skinny-fit jeans – nothing ruins the slick look of a tight-fitting pair of jeans like a handful of underwear bunching together down your leg. A pair of trunks will sit much closer to your skin, and since there is less material overall, will greatly reduce the odds of having to constantly adjust your underwear when they start riding up your favorite pair of 501s.

Trunks also offer temperature support for all seasons; the tight-fit helps with heat retention in the winter months to keep you nice and warm, and the slimmer design also works to keep you cooler in the swampy summer months.

If you’re on the shorter side, sliding on a pair of trunks will also accentuate your leg, giving you an added sense of height, as opposed to longer boxers which will actually make you look shorter.

Trunks may not be nearly as ubiquitous as briefs or boxers yet, but they might just be the most fashionable type of men’s underwear you can get today. Start stocking your wardrobe with these now and thank us later.

Cotton Spools


Even after you’ve narrowed down the type of underwear you want, there are still a myriad of materials available for each style, which will drastically affect the look and feel of your underwear of choice. Here are some of the best options to look out for.


Those extremely comfy briefs sitting in the back of your drawer are probably made from cotton, one of the most popular fabrics for men’s underwear. Cotton is light and breathable, which makes it perfect for wearing for extended periods of time. The only downside to cotton is that it absorbs moisture, so you’ll want to look for another fabric for your next workout session if you don’t want your area to get too swampy.


Unlike cotton, nylon will keep you dry even on the hottest of days or in the midst of a punishing gym session. Nylon is a synthetic polymer known for its stretching properties and rugged construction. If you’re going to be putting yourself (and your underwear) through the paces, nylon is a great bet.

Spandex is a synthetic fibre known for its extreme elasticity, making it a great option for exercising. You’ll generally find nylon or spandex in a fabric blend, so be sure to check the label before you buy if you want that extra bit of maneuverability in your underwear.


Polyester is another synthetic fabric that you’ll often find in underwear construction. Much thinner than cotton, polyester is light and durable, making it a great choice to pair with slim jeans.


The new kid on the block, modal fabric is made from beech trees, and is one of the most breathable fabrics you’ll find, making it a great fit for underwear. Modal is much softer than cotton, and will not shrink. It’s a tough fabric that is also extremely comfortable, which accounts for its surge in popularity in recent years.


If cost isn’t an issue, you can’t go wrong with silk underwear. Silk has moisture-wicking properties, which means it actually repels moisture, keeping your area nice and dry. Silk also has the benefit of working in any climate – it will keep you warm in the winter, and cool in the summer months. Silk is extremely soft, and the material practically shines, making it the ultimate example of luxury underwear. Treat yourself!


Cotton is by far the most popular fabric for men’s underwear. Cotton is light and breathable, which makes it perfect for wearing for extended periods of time. Modal is becoming increasingly popular due to its softness and durability, which makes it another great option. If money is no object, try splurging on a pair of luxurious silk underwear – we doubt you’ll go back to cheaper synthetic options after that.

Look, if you really need to ask this question, your underwear is probably too old and should be replaced. Underwear doesn’t come with an expiry date – if it’s filled with holes or has lost so much elasticity that it starts sliding down your legs, it’s time to put it out to pasture and get a fresh update. You never know who will see you in your underwear, so why not dress to impress just in case?

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