Best Underwear for Men 2023: All the Top-Notch Skivvies To Buy Right Now

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.

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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

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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

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The Best Boxer Briefs

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. 

The Best Trunks

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.

The Best Boxer Shorts

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.

The Best Budget Underwear

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.