If you’re trying to build a great wardrobe, your first step needs to be finding the very best underwear for men. Underwear is the first thing you put on, the last thing you take off, and the one garment that gets closer than any other to your, uh, prized possessions. More than you know, the wrong pair could throw off your whole day—or worse, your whole fit. (Ain’t nobody got time for bunching and chafing!) It’s for those very reasons that we firmly believe that you (yes, you) should spend a few extra dollars on top-quality skivvies when re-stocking your underwear drawer.
The Best Underwear Shopping Guide
- The Best Boxer Briefs: Calvin Klein cotton stretch boxer briefs (3-pack), $43
- The Best Boxer Trunks: Calvin Klein cotton stretch low rise trunk (3-pack), $29
- The Best Boxers: Polo Ralph Lauren classic fit boxer (3-pack), $45
- The Best Budget Underwear: Uniqlo AIRism boxer briefs, $15
- The Best Underwear for Hitting the Gym: Lululemon Always In Motion boxer, $28
- The Best Confidence-Boosting Underwear: Tom Ford silk-satin boxers, $310
- The Best Old-School Underwear: Sunspel superfine cotton trunks, $50
To put it in precious cargo terms, going budget on your underwear is like buying a car seat based solely on the lowest price (don’t do that). So break up with whatever shrink-wrapped eight-pack you’ve been buying, because a proper underwear restock requires the good stuff. We’re talking quality fibers that move with you, whether you’re shifting weight at a standing desk or going beast mode on some kettle bells (while we’re on the subject, underwear that prevents your privates from turning into a disgusting bog). We’re talking a cut that’s both comfortable and flattering. And we’re talking about a design that won’t raise eyebrows in the locker room or when your third date goes really well. That might sound like a lot to look out for in a simple pair of undies—and it would be, if we hadn’t already done all the looking for you—and settled on these 21 unassailable pairs for every taste and body type. From boxers to briefs to boxer briefs, here’s all the best underwear for men.
Need more detailed intel on all the best underwear out there? Start here:
The Best Boxer Briefs | The Best Boxer Trunks | The Best Boxer Shorts | The Best Underwear Brands
The Best Boxer Briefs
Calvin Klein cotton stretch boxer brief (3-pack)
$41.00, Amazon
Materials: 95% cotton, 5% spandex Sizes: S-XL Inseam: 4″ Fly: Functional side Colors and Patterns: Varies
The best men’s underwear that covers all the bases we just listed above? It still comes from the brand that changed the men’s underwear game in the first place: Calvin Klein. The American designer’s foray into men’s undergarments turned them from something guys had to wear to something they wanted to wear (and okay, yes, still had to), and maybe even wanted to show off. Plenty of it had to do with those ads, but most of the change happened because Klein and Co. started cutting them the way guys wanted to wear their underwear in the first place (read: not at their belly button). Cue the now-standard-issue below-the-navel stance, the wider waistbands (and yes, the logos on those waistbands), and the idea that underwear should show off your goods, not hide them. Add to that a super soft cotton blend with just the right amount of stretchy elastane, a waistband that’s equal parts robust and comfy, and a price (for two pairs!) that’s tough to beat, and you get an iconic pair of trunks that won’t be relinquishing its throne anytime soon.
More Boxer Briefs We Love
Boxer briefs are the reigning champ of the men’s underwear circuit. Like the polo shirt or the loafer, they’re hybrids that pull the best characteristics of multiple garments by wrapping them in one shiny package that’s more than the sum of its parts. (In this case, the security and support of tighty-whities and the coverage of boxer shorts.) Say less.
Tommy John Second Skin boxer briefs
$36.00, Amazon
Saxx Ultra boxer brief (3-pack)
$92.00, Saxx
The Best Trunks
Calvin Klein cotton stretch low rise trunk (3-pack)
$29.00, Amazon
Materials: 95% cotton, 5% spandex Sizes: S-XL, Inseam: 4″ Fly: Functional side Colors and Patterns: Varies
In our book, Calvin Klein’s boxer briefs are hard to beat. Are there more technologically advanced pairs? Yes. Are there pairs that are more breathable? We’ll give you that. But we just haven’t found a pair of underwear that does it all like CK does. And if your only gripe with the classic boxer briefs is that they’re just a tad too long for your liking, then don’t worry—they also come in trunk form. All the same great comfort, support, and flattering design that we love, with a slightly shorter inseam.
More Trunks We Love
No, we’re not talking swim trunks. We’re talking about boxer trunks, the in-between-in-between boxer briefs and briefs. They’re basically shorter boxer briefs, which means they’ll give you even more range of motion without sacrificing that crucial jewel support.
MeUndies Breathe trunk
$34.00, MeUndies
Mack Weldon Airknitx trunk
$30.00, Mack Weldon
The Best Boxer Shorts
Polo Ralph Lauren classic fit woven boxers (3-pack)
$53.00, Amazon
Materials: 100% cotton Sizes: S-XXL Fly: Functional, open Colors: Varies
Boxer briefs may dominate underwear drawers around the world, but there are scores of dudes who remain staunch boxer shorts devotees—and would happily trade support for a little extra air flow. Plenty of big-name brands offer a riff on the staple, but Ralph Lauren’s remains one of our favorites for a few reasons. For one, the brand’s classic-fit boxers are cut from the same type of lightweight, woven cotton it uses in its button-ups, and the relaxed fit offers ample room to stretch around in. But the real X factor is the functional fly, a rarity in the button closure-dominated boxer shorts space, making access easier in times of, ahem, urgency. On top of all that, the waistband also comes equipped with a clever hit of elastic that ensures they lay flat across the front for a clean finish.
More Boxer Shorts We Love
Before boxer briefs came along boxer shorts were the default, and for those of us who prefer a healthy breeze around our nether regions they’re a godsend. Unlike briefs, boxer shorts don’t cling to your body; their free-flowing silhouette lets your boys hang out unimpeded like Mother Nature intended.
Hanes tagless boxers (5-pack)
$22.00, Amazon
Uniqlo woven broadcloth boxer shorts
$8.00, Uniqlo
The Best Budget Underwear
Uniqlo AIRism boxer briefs
$15.00, Uniqlo
Materials: 89% polyester, 11% spandex Sizes: S-3XL Colors: Grey
We hate to compromise on anything as essential as underwear, but we’re also big fans of saving money. So what’s a frugal-minded skivvies-wearer to do? Head to Uniqlo, of course. The Japanese retailer’s primo underwear is a steal no matter how you prefer ‘em, but the best bang for your buck option is its AIRism boxer briefs. The retailer’s AIRism material is surprisingly lightweight and breathable which makes it perfect for hot weather garments and underwear, which is great news for those of us who run a little hotter than others. And at just $15, they’re a great value for all the performance you get.
More Budget Underwear We Love
You’d think that great underwear for a low price would yield…very few results. We’re happy to report just how wrong you are. There are a surprising amount of brands making affordable boxer briefs, trunks, and shorts with genuinely excellent materials and construction. Not convinced? Take a look for yourself.
Paul Smith stretch-cotton jersey boxer briefs (3-pack)
$50.00, Mr Porter
Kirkland Signature boxer brief (4-pack)
$17.00, Costco
The Best Underwear for Hitting the Gym
Lululemon Always In Motion boxer
$28.00, Lululemon
Materials: 91% Modal, 9% Lycra elastane, Sizes: XS-3XL Inseam: 5″ Fly: Non-functional Colors and Patterns: Varies
When you need your underwear to be as active and flexible as you are, try these unsurprisingly stretch-forward boxers from the first name in premium yoga gear. The four-way stretch fabric molds to your body and goes wherever you go while also retaining its shape. And no matter how steamy your workout sesh gets, they’ll keep things breathable and dry down low; as far as we’re concerned, they’re the best gym partner you could ask for.
More Gym-Ready Underwear We Love
No pain, no gain, the saying goes. But there’s no way in hell that means you have to suffer through a grueling workout with bad underwear that doesn’t stretch as much as you need it to—or keep your balls dry through your most strenuous HIIT routines.
Adidas performance boxer brief underwear (3-pack)
$36.00, Amazon
Stance Staple St boxer brief
$35.00, Amazon
The Best Confidence-Boosting Underwear
Tom Ford silk-satin boxers
$310.00, Mr Porter
Materials: 100% silk Sizes: S-XXL Fly: Functional, open Colors: Varies
If you’re looking for an extra-special pair to keep aside for your steamiest nights, you go to Tom Ford—a menswear god so inherently sensual he famously doesn’t wear underwear himself. “Let’s say you’re going on a date,” Ford told GQ‘s Mark Anthony Green back in 2018. “When you take off your pants, you want it to be kind of a great moment—which of course it will be when you take off your underwear. But before you get to that point, why wouldn’t you want silver metallic underwear? Or zebra? Or leopard? Or something a little crazier?” It’s hard to argue with that logic, especially once you see his signature skivvies up close. The zebra print is rendered in pure silk, with a touch of equally luxe velvet at the waistband—and it’s a boxer short, a cut we might not normally advise, but it’s a Tom effing Ford boxer short, so it feels sexy and just plain works. And it’s guaranteed to make for an unforgettable moment anytime you’re lucky enough to show ’em off.
More Hot N’ Steamy Underwear We Love
You don’t have to don a pair of cheetah-print underwear to feel sexy (with enough confidence, you don’t need any undies at all). But the right pair of skivvies can still boost your self-esteem tenfold.
CDLP boxer brief
$35.00, CDLP
Derek Rose “Woburn” silk boxer shorts
$85.00, Matchesfashion
The Best Old-School Underwear
Sunspel superfine cotton boxer briefs
$50.00, Mr Porter
Materials: 100% cotton Sizes: S-XXL Fly: Functional, side Colors: White and black
For going on 160 years now, UK outfitters Sunspel have been turning out some of the finest cotton goods on the planet: they invented the T-shirt, perfected the polo, and, to the surprise of no one, make a damn good pair of underwear, too. There’s something about crisp white undies that just feels practical, honest and true—and these boxer briefs live up to that billing. The jersey cotton fabric they’re cut from is soft and light, the elasticated hems keep them sturdy and fitted, and the fly-front pouch makes for easy, button-free access when it’s time to hit the bathroom. Just one more notch in the belt for the storied British maker.
More Classic Underwear We Love
All these newfangled startup underwear brands and synthetic-pumped boxer briefs are a bit too much sometimes. Who wants all those nasty chemicals near your most delicate assets anyway? Thankfully, there are plenty of other brands making underwear the old-school way, with all natural materials and traditional construction methods.
Merz B Schwanen 254 loopwheeled boxer briefs
$35.00, Merz B Schwanen
Industry of All Nation jersey boxers
$25.00, Industry of All Nations
A Couple More Underwear Brands Worth the Space in Your Drawers
Thus far, you’ve seen a lot of solid undies, but there are so many other options worthy of your attention. We realize we’ve doled out ‘best’ superlatives to a select few, but everyone’s preferences vary. These are a few other brands that also deserve a slot at the top of the charts.
Saxx Quest quick dry mesh boxer briefs (2-pack)
$61.00, Saxx Underwear
Hanro stretch-cotton boxer briefs (2-pack)
$75.00, Mr Porter
Everlane boxer briefs
$24.00, Everlane
Ron Dorff boxer briefs
$45.00, Ron Dorff
Originally Appeared on GQ
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