The 15 Best Pairs of Underwear for Men

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Your underwear is the backbone of everything you wear. It's essential, perhaps more than anything else in your closet; you know it's time to do laundry when you're out of clean underwear, and the same can't be said for, oh, we don't know, button-downs or hoodies. But no, really, you have to have your underwear!

And the thing is—you need (and deserve) underwear that is infallible. Sweat-proof and moisture-wicking options are great, sure, but meaningless if they don't fit right. A contour pouch is an added luxury. A waistband that doesn't roll over or squeeze into your stomach throughout the day is a necessity. That's why the styles we've gathered here are editor-tested, reviewed, and approved, so you can rest assured that your underwear isn't going to fail you.

It doesn't matter if you're a guy who likes boxers or briefs, plain or patterned, silk or cotton—you need underwear, regardless (unless you want to go commando all day and like, hats off to you). We have 15 of the best pairs for you right here, so you can breathe a sigh of relief and maybe put off doing your laundry for just a little bit longer.

18-Hour Jersey Boxer Brief

Mack Weldon made a name for itself in the fiercely competitive world of men's undergarments by letting its products speak for themselves. And we do have to say, that this pair of boxers is one of the most comfortable things you'll ever put on your body. Lightweight and ridiculously soft, they are designed for any and every day.

ComfortFlex Waistband Boxer Briefs (5-Pack)

Even after all these years, Hanes—an elder statesman of the underwear scene—still offers a value proposition that's tough to beat. There's a reason why they're America's number one men's underwear brand.

Boxer Brief

This one's for you, fly guys. Over a few short years, MeUndies has cultivated a surprisingly devoted following enamored with the brand's signature boxer briefs. This pair is the exact same boxer briefs as the ones you know and love, but this time with a fly. It's also designed with sustainably sourced mircromodal and a touch of elastane.

Boxer Brief

Everlane's super-soft supima cotton boxer briefs are backed by a 365-day guarantee, so on the off chance anything goes awry product-wise, you won't find yourself in an underwear-related bind. They're made with a close fit through the leg and a waistband that won’t roll. This option is the perfect first layer, at last.

Slim Fit Boxer

Nice Laundry's name speaks for itself. The upstart underwear brand reworks the classic woven boxer in knitted cotton with a touch of extra stretch, all in a slim-fitting silhouette cut snug but far from clingy. All we're saying is, you're a grown man; it's time to embrace the slim-fit pant party.

Velvet-Trimmed Satin Boxer Shorts

Tom Ford is the purveyor of high-end, luxe underwear, and the brand doesn't skimp on adding fun, bold prints to its superior fabrics. Best believe that its boxers will last you the long haul, and will give you an added touch of luxury where it matters most.

Microfiber Stretch Boxer Briefs (3-Pack)

Smooth, soft, and made of a microfiber stretch fabric? Now, nothing can come between you and your Calvins. This ultra-cozy microfiber pair will make you want to dance around in them all day—think Tom Cruise in Risky Business.

Cotton Modal Brief

Bombas doesn't limit itself to making some of the best socks out there. Its selection of underwear—including this brief made of a cotton-and-modal blend that's as soft as it is sturdy—is equally impressive. It's the type of underwear that makes you excited to open your drawer every morning.

Tag-Free Cotton Briefs (9-Pack)

Ah, the mighty, mighty white cotton brief—a.k.a., tighty-whities. It doesn't get any more classic than a pack of this underwear option, especially from Fruit of the Loom. And if Captain Underpants can rock the hell out of this look, we have no worries or doubts that you can too...

Always in Motion Boxers (5-Pack)

This is the good stuff. If you're going to trust any brand to outfit the lower half of your body in snug-fitting modal, it's going to be the one that outfits folks for working out and working with equal expertise. These boxers feature an ergonomic design and super-soft, quick-drying fabric for total comfort.

Sea Island Cotton Trunks

Sunspel doesn't use just any cotton; the brand uses super cotton, like this one, called Sea Island, which is completely organic and feels incredibly plush. This pair of trunks sit low on the waist with an elastic waistband and are close-cut for additional support. They're the type of everyday luxury that you'll want to invest in.

Plume G-String

Hom is a Jack-of-all-trades, master of many: the brand pretty much has every kind underwear style out there, including the highly-underrated G-string. We get that the thought is not everyone's cup of tea, but don't knock it until you give it a try. You never know, you might find that you really like the no-lined look.

Second Skin Relaxed Fit Boxers 3-Pack

Not too large, not too tight—these Tommy John boxers are the Goldilocks of underwear. A more relaxed fit for dudes who prefer a little extra room to breathe, they're made out of a supremely comfortable fabric that everyone will appreciate.

Microfiber Logo Boxer Shorts

Intimissimi's boxer shorts are some of the best quality on the market. Elegant comfort is the brand's aim, and elegant comfort is what it delivers. Plus, they make your ass look great—just saying.

Cotton Boxer Briefs (3-Pack)

Say goodbye to chafing and hello to your new favorite underwear with this three-pack of boxer briefs. Made with undeniably soft, mid-weight cotton, these briefs give you a body-hugging fit that allows you to breathe. This is truly one of those situations where if you don't get it, you'll regret it.

Tips For Choosing Underwear

As you’ve seen above, underwear is a category with many characters. The usual suspects: briefs, boxers, boxer-briefs. The outliers: long johns, thongs, jockstraps, and G-strings. What constitutes the best cut and length is dependent on what makes you feel comfortable. Ditto the fabric, because there’s no one be-all, end-all option.

Looking for something breezy that'll allow plenty of breathing room for your boys down below? Reach for some silky boxer shorts. Hate the feeling of your underwear riding up with even the most minute shifts in position? Consider buying a few well-cut briefs in breathable cotton. And if pure cotton isn't doing the trick, try a blend with nylon or spandex for added comfort and ease of movement. You could even invest in a micromodal pair—the latest fabric development in cutting-edge underwear technology—if you're in the market for undies specifically designed to wick away moisture and resist shrinking.

Why You Can Trust Esquire

We’re not going to say something is great unless it’s actually great. Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams.

When it comes to underwear, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our colleagues here at Esquire endorse for themselves. We’ve had to go through a lot of trial and error, and these underwear are the ones that are simply the best.

Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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