best in class

The Very Best Men’s Underwear

Whether you prefer briefs like Walter White, boxers like Tony Soprano, or perfectly in-between boxer briefs.

Best Men's Underwear
Photo: Marcus McDonald
Best Men's Underwear
Photo: Marcus McDonald

Trying to label a pair of underwear “the best” is a near-impossible task. Much like socks, the best men’s underwear should be comfortable, durable, and stylish. But those words mean different things for different people. I’m not here to settle the great brief-versus-boxer debate; which cut you prefer will always be a matter of preference. Because the nature of underwear makes it difficult to return if you don’t like how it fits, thinking about which length, style, and level of support you need is key to avoiding wedgies and the urge to constantly adjust your underwear. Below, I’ve found the best options in all categories based on fit, feel, and style by talking to stylists, fitness professionals, and other discerning and active men about the underwear they like best.

Best overall boxer briefs | Best ultrathin boxer briefs | Best designer multipack boxer briefs | Best less expensive multipack boxer briefs| Best performance boxer briefs | Best overall boxers | Best less expensive boxers | Best overall trunks | Best overall briefs

What we’re looking for

Style: There are three main styles of men’s underwear, and they are predominantly defined by how each one is designed to fit. Briefs — a.k.a. the “tighty whities” style famously worn by legendary television character Walter White — have a more snug fit and are cut to only cover your butt without extending to your legs. Boxers — which look more like regular shorts, as famously worn by legendary television character Tony Soprano — offer a more generous “boxy” silhouette and an average inseam of four to six inches. And the straightforwardly named boxer briefs are a hybrid style that combines the snug fit of briefs with the longer length of boxers. They were created in the early 1990s by designer John Varvatos, who cut the legs off a pair of long johns, and they went on to become one of the most popular styles of men’s underwear. A fourth, less common style is trunks, which are something of a middle ground between briefs and boxer briefs; they’re essentially boxer briefs with shorter leg lengths.

Materials and construction: Most men’s underwear is made of cotton or a cotton blend. Cotton is sturdy, breathable, and soft, which makes it well suited to everyday wear. Cotton is often blended with spandex or other synthetic fibers to add stretch, and performance underwear that’s designed to be worn for sports or during workouts is sometimes made with a mixture of nylon or spandex, which help it keep its shape, regulate body temperature, and dry quickly after exercise.

We also looked at how men’s underwear is constructed — inspecting the seams and where they’re placed, how the waistband is built, and the style of the fly if there is one. Most of the brands we’ve recommended below do have a fly, but a few no-fly designs have gained popularity among men who prefer slim-cut or skinny pants. The style of the fly can also vary; the most common versions are a traditional vertical fold-over fly, a button fly, and a horizontal fold-over fly that is supposed to feel more secure. I tend to avoid the button fly, which usually shows up on boxers and which I’ve mostly found to be a nuisance; despite being secure, it adds a tedious extra step to using the bathroom, and I feel like I’m standing at the urinal for longer than necessary. Briefs and even boxer briefs with the more traditional vertical fold-over fly tend to offer the most easy access in that regard.

Fit and support: Style, materials, and construction are all directly correlated to how a pair of underwear will fit, the level of support it offers, and how well it will stay put as you move. Briefs are the most supportive but can sometimes feel restrictive. Both briefs and boxer briefs provide more support than boxers. Boxers are the loosest and most free-flowing, which can be comfortable but make them likelier to bunch up under your pants.

You should also pay attention to the waistband style, and whether the elastic is bare or covered by cotton, as that can affect whether the underwear rides up or slides down when you move.

The last pieces of the underwear puzzle are the rise and the inseam, and your preferences may depend on what type of pants you like to wear. In my own experience, low-rise underwear sits too far down on my hips, and I find it generally uncomfortable. But for someone who prefers low-rise trousers, a low-rise pair of underwear will be a better fit. Regular-rise underwear sits closer to the waistline and, for me, feels more supportive.

Boxers have the longest inseam at four to six inches. Briefs rarely have any inseam to speak of; instead, they usually have elastic seams around the leg openings. Predictably, boxer briefs fall somewhere between and often have an inseam between three and five inches, depending on the brand.

Best overall boxer briefs

Boxer briefs | Supima cotton | Traditional fly | Regular rise | Sizes S–3XL

Boxer briefs were the most popular underwear style among the men we spoke to. Derek Guy, editor at men’s style website Put This On and blogger at Die, Workwear insists, “They’re infinitely better than boxers” because he likes the added support and the fact that they don’t bunch up in your pants. Uniqlo’s Supima Cotton Boxer Briefs were a clear standout among our panel, receiving multiple recommendations. The simple and affordable design has a regular rise and a vertical fold-over fly. “They’re soft, breathable, and keep their shape well even after many washes,” says photographer Sam Schmieg, who “wore Calvin Klein for a minute but, at this price and comfort level, couldn’t pass up Uniqlo.” Elliott Foos, formerly the director of coffee at Daymoves in Williamsburg, says, “Uniqlo’s basics are unrivaled, and these carry the torch.” Foos added that that he’s been “into these for three-plus years (I’ve been reupping, don’t stress), and I still love them.”

Best ultrathin boxer briefs

Photo: retailer

Boxer briefs | Polyester, spandex, and nylon | Traditional fly | Regular rise or low rise | Sizes S–3XL

Uniqlo’s AIRism line is all about performance; Uniqlo promises moisture-wicking technology intended to keep you cool, dry, and feeling fresh. These AIRism boxer briefs are especially lightweight and breathable. Nicolás Lazaro, a community specialist at menswear resale platform Grailed, says he used to wear cotton boxer briefs but has “never looked back” since switching to these. “You’ll forget you even have them on,” he says, describing them as “ultralightweight, breathable, and moisture-wicking, with enough stretch for comfort while still providing the necessary support.” They come in two rises with a traditional fly and a generous inseam of roughly four to five inches depending on the size you wear. During my own testing, these briefs held up well over multiple washes and didn’t shrink in the dryer. Lazaro notes that they dry so quickly that he can just hand-wash them and hang them up for a bit if he’s ever in a pinch.

Best designer multipack boxer briefs

Boxer briefs | Cotton | Traditional fly | Regular rise | Sizes S–XL

It’s hard to think about mens underwear without thinking of Calvin Klein, a brand that transformed something men often overlook into a quasi-sexy status symbol. Phillip Wong, co-founder and creative director of Hawthorne, says the brand’s underwear is still some of the best out there. Calvin Klein became known for its provocative ads featuring stars like Mark Wahlberg and Antonio Sabato Jr. in the ’90s and Justin Bieber more recently. The ads changed how people thought of men’s underwear, and Calvins have maintained their status as cool-kid luxury underwear ever since. “I’ve worn the classic Calvin Klein boxer briefs for as long as I can remember,” Wong says. “The shape is exceptional, not too tight, and it’s very low maintenance.” They feature a regular rise, a traditional fly, and an inseam that sits around the lower thigh. They come in packs of either three or five pairs and a variety of colors. Chris Echevarria, creator of the footwear brand Blackstock and Weber, says, “I don’t think anyone does underwear better than Calvin. If it’s good enough for Marty McFly, it’s good enough for me.” Ian Taylor, the former editor-in-chief of men’s style site FashionBeans, is another fan. But he suggests avoiding the white Calvins and sticking to black or gray: “In photo shoots, you often see people wearing white, which looks great when it’s well-lit and photographed on a model with a six-pack. But if you’ve been wearing them for six months, they won’t look quite as pristine,” he says.

Best less expensive multipack boxer briefs

Boxer Briefs | Cotton | Traditional Fly | Regular Rise | Sizes S-2XL

Queer Eye stylist Tan France is a massive fan of the Hanes underwear line. He suggests these lightweight cotton boxer briefs, which he wears daily and which will suit those who wear slim pants and want to avoid bunching or visible seams. They have a classic elastic waistband, a traditional fly, and a regular rise, and they are designed not to ride up on the legs. Tim Melideo, who runs Stay Classic, a men’s fashion website focused on affordable style, says he’s long sworn by them: “They’re simple and inexpensive, and they last.”

Best performance boxer briefs

Boxer briefs | Nylon | Traditional fly | Low rise | Sizes S–2XL

Barron Cuadro, founding editor of Effortless Gent, calls the Exofficio a “long-term favorite” boxer brief designed with more rigorous activities in mind. “They are designed for outdoorsmen, so they’re anti-microbial and they dry superfast,” Cuadro tells us, adding that he’s been wearing his pairs for six years. He likes that they’re made of breathable fabric, and says that even with the lower rise, they are comfortable. “If you’re a hard-core wilderness guy, you can wash these in a river and they’ll be dry within an hour, so they can definitely handle a sweaty workout.”

Best overall boxers

Boxers | Cotton | Traditional fly | Regular rise | Sizes XS–2XL

For those seeking a classic pair of boxers, Sunspel has been making underwear since 1860 and introduced the boxer short to Britain in 1947. Daniel Brøndt, creator of the menswear brand Another Aspect, says Sunspel has made “just a few tweaks here and there over the years, and it’s still constructed from the finest cotton there is.” He describes these boxers as “lightweight, breathable, and designed with smooth double-turned seams.” The rear of the boxers have a back panel instead of a central seam, which some men find more comfortable. Thomas Fortune, the creative director for footwear brand Stubbs & Wootton, says, “The only time I would venture away from Calvin is for Sunspel’s cotton boxer shorts.” Menswear consultant Nick Wooster is also a fan of them, particularly in this Oxford-blue color.

Best less expensive boxers

Boxers | Cotton | Traditional fly | Regular rise | Sizes XS–2XL

For a more affordable pair of boxers, celebrity stylist Neil Cohen suggests this pair from J.Crew. “I just wear them for sleep, but some guys still wear them” as underwear, Cohen says of the brand’s cotton boxers, which come in a variety of fun prints. “They’re really well priced,” he says, adding that the 100 percent cotton fabric “has a nice hand feel.” These boxers have a four-inch inseam, a traditional fly, and a cotton-covered elastic waistband, and they’re available in a wide range of colors and patterns.

Best overall trunks

Trunks | Micro-modal and spandex | Horizontal fly | Regular rise | Sizes XS–2XL

Cuadro likes these trunks by Tommy John, which are made from a blend of micro-modal and Spandex for stretch. Micro-modal is a type of fabric that is known for its softness and resistance to shrinkage; it also has moisture-wicking properties. “The modal blend is supersoft, comfortable, and relatively quick drying,” he says, adding that these “just feel great when you have them on.” Adding to their comfort is a “nice and wide” waistband, according to Cuadro, and they have a horizontal fly designed to provide extra support and feel more secure.

Best overall briefs

Briefs | Cotton | Traditional fly | Regular rise | Sizes S–XL

Many of the stylists and fashion pros we spoke to tended to prefer briefs for the way they easily disappear under trousers. Cohen likes the style because it doesn’t “ride up” on the leg or “add any extra bulk” when wearing slim pants, which can sometimes happen with boxers or boxer briefs. Calvin Klein’s cotton briefs, widely considered to be an all-time classic of men’s underwear, are a clear standout. Fashion and branding consultant Ronny Oppong, barber Mark Miguez, and stylist Brandon Garr all praised these, which are made of cotton with a regular rise and a traditional fly. They also have a nice elasticity around the waist and come in a variety of colors, and the leg openings aren’t too restrictive.

Some more men's underwear we've written about

Our experts

Chris Black, former Strategist columnist
• Daniel Brøndt, creator of the menswear brand Another Aspect
Andrew Chen, founder of menswear brand 3sixteen
Neil Cohen, celebrity stylist
• Barron Cuadro, founding editor of Effortless Gent
• Chris Echevarria, creator of the footwear brand Blackstock and Weber
Christopher Fenimore, street-style photographer
• Elliott Foos, former director of coffee at Daymoves
Thomas Fortune, creative director for footwear brand Stubbs & Wootton
Tan France, Queer Eye stylist
• Brandon Garr, stylist
• Derek Guy, editor at Put This On and blogger at Die, Workwear
Nicolás Lazaro, community specialist at the resale platform Grailed
Malcolm McNeil, photographer
• Tim Melideo, editor of Stay Classic
Mark Miguez, barber
• Ronny Oppong, fashion and branding consultant
Sam Schmieg, photographer
• Ian Taylor, the former editor-in-chief of men’s style site FashionBeans
• Phillip Wong, co-founder and creative director of Hawthorne
Nick Wooster, menswear consultant

The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best men’s wardrobe basics, white T-shirts for men, jeans for men, white sneakers for men, and flattering clothes for men. We update links when possible, but note that deals can expire and all prices are subject to change.

The Very Best Men’s Underwear