The Best Men’s Underwear

Underwear is often overlooked. 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. It happens. 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). You’ll feel better if you switch them out. I promise.

Here’s a tip. It doesn’t necessarily mean that you have to replace your old pair with the same style. There are many styles and options in fabrics such as cotton, merino wool, and high-performance synthetics, and they come from both old and new brands. Before you compare things like stretchiness and softness, it’s important to know the basics of each style.


Briefs are the most practical type of underwear because they have a supportive fit, no creeping tendencies, breathable fabric, and a 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 clever combination of boxer briefs and traditional shorts gives you the support of shorts while also providing more coverage. TheHybrid style is comfortable, supportive, and flattering.

Trunk Briefs

Trunk briefs fall somewhere between boxer shorts and traditional 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 created to allow boxers the same freedom of movement that shorts used 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. Modern styles come in a range of fabrics that can be used for both everyday wear and sports. 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.

It’s simple, right? It’s true. This is a simple concept to remember. But it’s important to remember there are other brands, not just shapes. Although it might seem difficult to get rid of your Champion, Fruit Of The Loom, Ethika or Hanes habits, it is possible. You can ditch the hard, scratchy cotton for soft, moisture-wicking alternatives. It’s well worth it!

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


CDLP, a Stockholm-based basics brand, produces a variety of modern takes on wardrobe staples for men. Every release blends stylish designs and interesting materials, from T-shirts and swim pants to performance wear and pajamas. For example, these Boxer Shorts. Lyocell is a rayon-like fabric made from less water than cotton. They’re breathable and moisture-wicking. These briefs are looser than the boxer shorts, but not too wide.

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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

TheBoxer shorts have been around since the mid-1980s.90s. It was officially invented by John Varvatos, the then Head of Menswear at Calvin Klein. Calvin Klein has been synonymous with skivvies since then. They’ve made the category very sexy for all sexes. You can thank social media, influencers, and catchy marketing (#mycalvins), but they have been a pillar of the category since its inception. 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 is known for their BallPark Pouch. It has nothing to do with baseball. It’s a place for men to park their… They say it gives them a sense of security. “boost,” but really it’s the security of compression shorts without extreme tightness. Shopping on their site is easier than shopping elsewhere’s because they break down their underwear collection by silhouette and activity. For example, bottoms that are suitable for running or lounging are not included in the same category. 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’s men’s collection of underwear includes all styles. The brand has you covered, with everything from long boxers and leggings to shorts and square-cut bottoms. 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.


KOTN, a basic brand, has steadily expanded its range of T-shirts and Tanks to include ultra-soft underwear and camping 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. The brand offers a wide range of options and comes in five sizes. The Always In Motion pack boasts three pairs all made from Modal, a super-soft alternative to cotton. They are stretchy and have a 5-inch inseam.

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. The German company makes underwear from organic cotton using classic standards with some sensible updates. Plenty of them still feature button fronts, but this boxer brief has a vertical fly and a form-fitting circular waistband.

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Mack Weldon

Mack Weldon was one of the first everyday brands to embed silver into its line of men’s essentials. Although it is used in high-performance settings, such as NASA research, and sporting events at the Olympics, its use in boxers was not justified. It is anti-microbial and promises a longer shelf life. They mix it into their Supima boxers with cotton, but they use jersey for the 18 Hour line. The name of the line is based on how long the fabric sits prior to being cut. TheA longer wait time means 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 difficult to forget Nike, the sportswear giant that can produce redesigned versions of their compression wear almost every month. While most of their styles are designed for those who wear compression wear under their workout clothes in the winter, they can also make double-duty undershorts for 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. They also offer a complete line of organic men’s underwear. (Hence, the name. Boxer Shorts and Boxers can be divided into two different categories. Both are soft and breathable, but the Boxer Shorts are wider due to the looser fit around the legs. They are more expensive but they are a result of their commitment for better materials and processing.


It’s always been commonplace for the waistband on men’s underwear to flaunt a brand’s logo. Everlane loves to emphasize that their pairs do not have this logo. 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. TheLonger Briefs cover more of the man’s leg. This ensures they won’t ride up in motion. They are available in a range of colors.


Municipal makes three different types of underwear, their Everyday Boxer Brief, the Tech Bodymap Boxer and these Stealth Cropped Leggings. Each one offers different performance benefits and is made from a mix of spandex and polyester. TheCropped leggings are shorter than crew socks. This ensures fabric doesn’t get doubled up and reduces breathability. These leggings are smart for intense workouts but won’t show underneath normal trousers.


No, Smartwool hasn’t developed an intelligent fabric capable of cooling you on command. However, the technical achievement of Smartwool’s use of merino Wool should also be celebrated. 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

Start-ups are often able to offer solid alternatives in a category that has been dominated for decades by established big-box stores. (See, for instance, socks.) Sir Cadian went one step further with their products, promising comfortability for their customers, as well as a commitment to the environment. 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. 

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Entire world

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 many colors to choose from.

Duluth Trading Co.

When you think about men’s underwear, Duluth isn’t the first thing that comes to mind. Don’t Sleep! Although the patterns and illustrated product photos are not the most flattering, the options are great and some of the most wearable we’ve ever tested. They don’t lose their shape even after repeated wear or washing. 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 is 100 percent cotton. Stretch uses 92-percent cotton. Cellular is 100-percent Cotton with an open knit for increased breathability. While there aren’t many brands that make better underwear, the price points might discourage even the most expensive shoppers. See the $90 dollar Sea Island Brief, for example. But it’s worth it, I’d argue.


Uniqlo taught me something. Most times, you buy something there knowing it’s cheap — but then it’s better than excepted! You can find a wide range of Supima Cotton and Airism options in their underwear. These are the aforementioned Supima Cotton bottoms, which are odor resistant, stretchy and yet capable of holding their shape. You should remember that they can withstand repeated wear even though they cost less than $7 dollars.


Hanro, a Swiss brand, offers a wide range of men’s and women’s underwear. Each has its own tradition. (TheCompany’s that are more than 137 years old. Take this brief, for example. It’s made of a mixture of long-staple Egyptian cotton elastane and has a higher waist. The flattering lay-flat construction is also included. These are definitely an upgrade to your standard, big-box brand style.

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