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The Best Men's Underwear

20 brands making underwear you'll enjoy wearing.


Too much of the time, underwear is an overlooked part of the wardrobe. Relegated to the backs of dark dresser drawers and thoughtlessly shuffled on every morning, it suffers from neglect: maybe you’re stuck in a rut, busy with life or spending money elsewhere. It happens. But, refreshing your underwear is as important as buying a new toothbrush. What’s more, the new set provides comfortability and looks quite good (especially compared to those you've owned for the better part of a decade). Switching them out will make you feel better, too. I promise.

Here's an important tip, by the way. Just because you're swapping out old pairs doesn't mean you need to replace them with the same style from the same brand. There are numerous styles and countless options available in fabrics like cotton, merino wool and high-performance synthetics out there, from brands both new and old. But, before you begin comparing things like stretchiness, softness, and shape, learn the basic styles first, because it's easy to call one pair one thing when it's really something else: aka when you broadly call a style boxers when they're actually boxer briefs.


Briefs might be considered the most practical underwear due to their supportive fit, non-creeping tendencies, breathable cotton fabric and no-nonsense waistband. And there’s nothing inherently wrong with white cotton, but there’s a range of colors and patterns available depending on your taste. Other options are made with odor-fighting merino wool, cooling bamboo fibers and breathable synthetics — all worth a look.

Boxer Briefs

In the mid-’90s, John Varvatos — then the head of menswear design at Calvin Klein — invented the boxer brief. This brilliant melding of boxer shorts and traditional briefs boasts the support of briefs while providing additional length in the leg for more coverage. The hybrid style is both comfortable, supportive and flattering.

Trunk Briefs

Trunk briefs toe the line between traditional briefs and boxer briefs. Longer than the former and shorter than the latter, they essentially have the same cut as Sean Connery’s swim trunks in Goldfinger, hence the name. Again, because they’re a bit longer than the traditional brief, they appear more modern than traditional briefs. Definitely geared more for the athletically focused, they’re supportive without feeling restrictive in the upper leg.

Boxer Shorts

Boxer shorts were designed to provide the same freedom of movement as shorts worn by boxers. Typically made of materials like cotton and silk, the only restrictive part of this underwear is the elastic waistband — the rest of the boxers are designed to fit loosely. They’re an incredibly comfortable option that’s become one of the staples.

Long Underwear

Long underwear doesn’t just come in waffle-knit cotton. In fact, newer styles are made with a host of new fabrics suited for everyday wear and athletic endeavors. Appropriate for the coldest months, long underwear is a necessary base layer to keep you comfortable — styles are available from both performance and heritage brands.

Easy, right? Right. Truly a breeze to remember, but it's also important to remind yourself that there are other brands out there, too, not just shapes. It might be hard to kick your Champion, Fruit of the Loom, Ethika, or Hanes habit, but you can do it. Ditch the scratchy cotton in favor of softer, moisture-wicking alternatives. It's worth it!

Here are the brands — from acceptable classics like Calvin Klein to sustainable upstarts like Sir Cadian — making the best men's underwear.

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Stockholm-based basics brand CDLP produces an assortment of updated takes on men's wardrobe staples. From T-shirts and swim trunks to performance wear and pajamas, every release blends interesting materials and style-forward designs. See these Boxer Shorts, for example. Cut from Lyocell, a rayon-like fabric that's softer than cotton but uses less water, they're breathable, moisture-wicking and naturally anti-bacterial. For those who don't like the tightness boxer briefs offer, these come with a looser cut without being too wide open.

Nice Laundry

Born out of a Kickstarter campaign, Nice Laundry makes socks and underwear you can wash with pride — hence the name. All kidding aside, the company covers two of the classic styles, boxers and boxer briefs, but offers updates to both: the fly sits horizontally; there's anti-rise ribbing on both legs; they're odor-resistant; and you can customize your own pair with tiny logos or monograms. The Boxer Brief in grey offers a pleasant blank canvas.

Calvin Klein

The boxer brief style has only been around since the mid-90s. It was officially invented by John Varvatos, the then Head of Menswear at Calvin Klein. Ever since, Calvin Klein's become synonymous with skivvies. And they've made the category rather sexy for all genders. Thank social media, influencers or catchy marketing (#mycalvins), either way, they've been a pillar in the category since they launched. Now they come in an array of colors and cuts, but you can't go wrong with the classic Cotton Stretch boxer brief in black — in a 3-pack, of course.


Saxx specializes in something they call the BallPark Pouch. And it has little to do with baseball. Instead, it's a slot for men to park their... you know where this is going. They say the feature gives them a "boost," but really it's the security of compression shorts without extreme tightness. Plus, shopping on their site proves easier than on others', because they break out their underwear collection by both silhouette and activity. Bottoms for running, for example, aren't listed alongside ones for lounging. The pair pictured here is their Vibe Trunk, a versatile option that's tight through the legs and butt and features the aforementioned pouch.

Tommy John

Tommy John collection of men's underwear covers the entire spectrum of styles. From longer boxers and leggings to briefs and square-cut bottoms, no matter your preferred fit, the brand's got you covered. But we'd be remiss not to mention one line, in particular, the ultra-soft Second Skin collection. Pictured here as a brief, these iterations are cut from non-pilling micro modal fabric and feature a subtle built-in pouch and non-roll waistband.


Since 2015, basics brand KOTN has steadily grown its collection from standard T-shirts and tanks to ultra-soft underwear and camp shirts. But, sometimes, the classics remain the most popular — and for good reason. Their standard Boxer Brief cut from 94-percent Egyptian cotton remains a pair of underwear you don't have to worry about: they're moisture-wicking, breathable and a great value.


It's no surprise that a brand nearly synonymous with stretch wear makes excellent underwear. Their options are flexible, come in five sizes, and offer a variety of fits. The Always In Motion pack boasts three pairs all made from Modal, a super-soft alternative to cotton. They stretch and have an inseam of 5-inches.

Merz B. Schwanen

Made on loopwheelers that are more than 100 years old, Merz B. Schwanen's basics are the ultimate upgrade — in an old-world luxury kind of way. Using organic cotton, the German company constructs underwear to classic standards, with a few sensible updates. Plenty of them still feature button fronts, but this boxer brief has a vertical fly and a form-fitting circular waistband.

Mack Weldon

Mack Weldon was one of the first everyday brands to embed silver into its line of men's essentials. While used in high-performance settings like research studies at NASA, sporting events at the Olympics and the ilk, its presence in boxers, for example, was unfounded. It's anti-microbial and promises longer freshness. They mix it into their Supima cotton boxers but use jersey for their 18 Hour line, which is named after how long the fabric sits before it's cut. The longer wait period makes for a softer, more consistent fabric. This is most evident in the 18 Hour Boxer Brief, a soft and appropriately spacious iteration that comes in a dozen colors. 


It's hard not to mention Nike, the sportswear giant capable of churning out revamped versions of their own compression wear nearly monthly. Most of their styles are catered to those seeking something to wear under their workout clothes, but that doesn't mean they can't do double duty undershorts in the summer. The Nike Elite Micro offers a contoured look with super soft seams and a waistband you won't notice.

Organic Basics

Long johns make sense whenever the weather shifts from warm to cold — or when you're out camping or spending an evening or early morning outdoors. Organic Basics makes them in two weights, this lighter option made from Tencel and heavier running tights. But that's not all: they have an entire line of men's underwear made from organic materials. (Hence the name.) Divvied up into two categories, Boxer Shorts and Boxers, both are soft and breathable but the former is wider, signaled by the loose fit around the leg. They're pricier, but the price tag is a product of their commitment to better materials and processes.


It's always been commonplace for the waistband on men's underwear to flaunt a brand's logo. Everlane loves to point out that their pairs come without that. But, that isn't the only area of improvement: these are softer, wash-tested up to 50 times, feature a 4-inch inseam, and come in a 93-percent Supima cotton, 7-percent elastane construction. The Longer Brief strives to cover more of every man's leg, ensuring they won't ride up when you're in motion. Plus, they come in an array of colors.


Municipal makes three different types of underwear, their Everyday Boxer Brief, the Tech Bodymap Boxer and these Stealth Cropped Leggings. Each offers various performance benefits, but all come constructed from a blend of polyester and spandex. The cropped leggings stop short of where crew socks would sit, ensuring fabric doesn't get doubled up, thus reducing the overall breathability. Sure, these are smart for intense workout sessions, but they also won't show from under usual trousers.


No, Smartwool hasn't developed an intelligent fabric capable of cooling you on command. However, the way they've leveraged merino wool should be heralded as a technical achievement, too. Merino proves light, breathable, and naturally odor-resistant. These Merino 150 Boxer Shorts boast all of these and more, too: there's embedded nylon for added durability, flat seams to prevent chaffing and a nearly invisible fly that's still fully functional. 

Sir Cadian

As a category dominated by decades-old big box store brands, start-ups oftentimes find success through simply offering solid alternatives. (See: socks, for example.) Sir Cadian took their products one step further, promising a commitment to their customers' comfortability but also the planet, too. The brand uses sustainable (yet undoubtedly soft) materials like Tencel Modal, bamboo, and organic cotton, palm tree nuts for buttons, and elastic-free waistbands. They've been designed as sleepwear, but their Boxer Briefs can be worn anywhere. 


The strangely childish descriptions on Entireworld's underwear aside — see: "synthetic free peen" — the brand makes plenty of excellent options. All of them emphasize organic materials and comfortable silhouettes, plus sensible subtlety. Pick the Organic Cotton Trunks if you're seeking something stylish, safer for the environment, and long-lasting. There are lots of colors to choose from, too.

Duluth Trading Co.

Duluth doesn't come to mind when you think of men's underwear? Don't sleep! Although the patterns and illustrated product images aren't the most flattering, their options feel great and are some of the hardest-wearing we've tested. They don't lose their shape in the wash or through rigorous wear. Plus, this pair, the Buck Naked Performance Boxer Briefs, comes in sizes small through 4XL.


If you want a classic pair — something kids and dads alike would call "tighty whities" — go see Sunspel. Not only do they have a collection of whites called Sea Island Cotton, but they make three others, Superfine Cotton, Premium Stretch, and Cellular Cotton. Superfine uses 100-percent cotton, Stretch employs 92-percent cotton and 8-percent elastane, and Cellular are 100-percent cotton with an open knit for added breathability. There are few brands making better underwear, but their price points might deter even the splurgy shopper. See the $90 dollar Sea Island Brief, for example. But, well worth it, I'd argue.


I've learned something about Uniqlo. Most times, you buy something there knowing it's cheap — but then it's better than excepted! Such is so with their underwear, an assortment of Supima Cotton, Airism (a blend of breathable materials), Woven Cotton options. These are the aforementioned Supima Cotton bottoms, which are odor resistant, stretchy and yet capable of holding their shape. Reminder: just because they're under $7 dollars doesn't mean they won't endure repetitive wear.


Swiss manufacturer, Hanro, makes a lengthy catalog of men's underwear, each with its own hint of tradition. (The company's over 137 years old.) Take this brief, for example. It's made from a mix of long-staple Egyptian cotton and elastane, has a higher waist and a flattering lay-flat construction. These are certainly an upgrade on your usual, big-box brand styles.

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