Buddy, It's Time to Buy Better Underwear

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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 All-Around Underwear: Calvin Klein cotton stretch boxer briefs (3-pack), $43
• The Best Budget Underwear: Uniqlo Supima cotton boxer briefs, $8
• The Best Boxers: Polo Ralph Lauren classic fit boxer (3-pack), $43
• The Best Underwear for Hitting the Gym: Lululemon Always In Motion boxer, $28
• The Best Hot ‘n Steamy Underwear: Tom Ford silk-satin boxers, $310
• The Do-No-Harm Sustainable Boxers: Industry of All Nations organic cotton woven boxers, $25
• The Best Confidence-Boosting Underwear: CDLP boxer briefs, $35
• The Best Old-School Underwear: Sunspel superfine cotton boxer briefs, $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. 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 30 unassailable pairs for every taste and body type. From boxers to briefs to boxer briefs, here’s all the best underwear for men.

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 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.

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 Supima cotton line. Supima cotton is prized for its ultra-silky feel and durable make, both attributes you’ll appreciate when you slip on a crisp pair of these each morning. In other words, it’s the kind of material that feels like an honor and a privilege to touch, let alone for just $8 a pop.

The Best Boxers

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 easier to access 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.

The Best Underwear for Hitting the Gym

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.

The Best Hot ‘n Steamy Underwear

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.

The Do-No-Harm Sustainable Boxers

25 years ago, big, billowing boxers were the undisputed champion of the men’s underwear world. As pants got slimmer, underwear naturally got tighter. But as men’s trouser trends swing the other direction towards fuller (sometimes giant!) silhouettes, something that allows for a little more room is back on the table as a viable—and seriously comfortable—option. That doesn’t mean you have to rush out and pick up a pair of critter print boxers just yet, though. Instead, ease back into the free-wheeling thighs era with something that puts coziness first, like these mega eco-friendly boxer shorts from Industry of All Nations. Most clothing today uses a whole host of chemicals, egregious amounts of water, and synthetic materials that take centuries to break down. Nasty stuff. IOAN’s undies are the complete opposite. They’re au naturel courtesy of an undyed, unbleached cotton and an elastic-free drawstring waistband, which means you can breathe easy knowing your underwear is as sustainable as can be.

The Best Confidence-Boosting Underwear

We’re not quite sure how CDLP makes their underwear feel so damn sexy, and at a certain point, we gave up trying to figure it out. Maybe it’s the insanely flattering cut, they way they hug your quads (and protect your valuables) like they were custom-fit exclusively for your gams by a bespoke skivvies operation. Maybe its their ridiculously dreamy feel, thanks to the brand’s generous use of lyocell, a silk-like material that’s much stretchier and just as smooth. Or maybe it’s the fact that that managed to nail that innate sexiness without the help of any kitschy prints, just a brooding expanse of sleek, unadulterated black. Who cares, really? Asking the questions is half the fun. 

The Best Old-School Underwear

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.

Plus 12 More Pairs We Love