The Best Men's Underwear You Can Buy In 2020

The boxers and briefs that will make you look your best in the (almost) altogether.
IMAGE Lionsgate Films

According to Philip Tierno, professor of microbiology and pathology at New York University, underwear isn't built to last. That's because a lot goes on down there. And, also, because nothing we wear daily can survive the travails of 21st-century life (well, apart from really well-made Swiss watches). It means you should be refreshing your underwear drawer every year, at the very least. It also means you should be refreshing your underwear drawer with quality: things that are designed to be worn 365 days of the year (very regular hot washes in-between also – that's very important).

This proposed lifespan rubbishes the idea of lucky pants, then. Anyone who deems a go-to pair as such will absolutely be not 'getting lucky' – and especially if said pants don't even suit them. Because in addition to design, and comfort, different pants are specially built to suit different builds. It's not just a binary choice of 'normal' and 'model', either. Some pants are better for thicker thighs; others, narrower waists.

Instead, you should think of your underwear as the foundation around which you build the rest of your outfits. It might not be seen, granted. But it might! So you should care, and not just wait for the inevitable pair of half-decent pants to have your name on under the Christmas tree.

You'll look better. You'll feel better as a result, and that sort of confidence is quite important when you're entertaining company in your underwear. If you really want to get lucky, read on below.



Mix Modal Trunks,

Photo by American Apparel.

Best brands: Hanro, Derek Rose, CDLP

Best for: Slighter frames, or trimmer frames, or both

Best example: Shawn Mendes in That Ad Campaign which caused adolescence as we know it to implode.

Not to be confused with the hybridous boxer-brief (more of which later), trunks are arguably the newest – and most comfortable – development in the world of men's underwear. They look a lot like other options too: they've the snugness of a brief, the shape of a boxer, and the best-of-both-worlds of the boxer-brief. But what separates trunks is the leg length: this sits just below that crease where thigh meets pelvis, hence, trunks.

Okay, that sounds very uncomfortable and chafing. Though in reality, trunks are specifically designed for comfort. Where skinnier legs suffer ruching, pooling fabrics from underwear that won't quite behave under jeans or trousers, trunks have minimized that risk altogether. And, with a cut-off at the widest point of the thigh, they can make your legs look less yeah-I-only-do-leg-day-once-a-month, and more yeah-I-can-crush-a-watermelon-with-these-thighs-and-what-of-it.

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If you're not sold on that (and you should be), know that trunks, generally speaking, involve a lower rise waistband too. That means no pants being twisted by a tighter-than-usual pair of trousers, and more exposure to the Adonis abs you've no doubt gleaned in lockdown.

Two Pack Organic Cotton Boxer Trunks,

Derek Rose Black Hipster Trunks,



Y-Brief (£28) at

Photo by CDLP.

Best brands: Emporio Armani, Tom Ford, Orlebar Brown

Best for: Chunkier thighs, rugby player types, Jacquemus models (or maybe all three)

Best example: Magic Mike, and all those other strapping lads in an amateur rugby club charity calendar.

The classic brief: a tale of two cities – one of which is having more sex than a retired HBO series about four single New Yorkers. In this camp, the brief is an artifact of that largely Italian strain of prurience, all tied together in a tight and comfortable package south of a big brand waistband (and often seen on silk sheets and silkier advertising campaigns). On the other, it's a sensible, no-frills option that was lifted from mummy's boy territory into retrocool waters by the likes of American Apparel, and other nodders to the Seventies.

Both approaches are absolutely fine, and the brief is a happy juncture between each aesthetic. What's more, its benefits are myriad. As the brief is largely defined by its cropped style that exposes most of the leg, it is ideal for those that have plenty of mass in those parts. But on the other hand, shorter guys stand to benefit: more leg exposed creates the illusion of a longer leg and a longer man.


Let us be clear, too. When things are snugly compacted, they can also look bigger. You work it out.

Tom Ford Black Cotton Briefs,

Orlebar Brown Pale Grey Melange Slip Briefs,



Best brands: Sunspel, M&S, Hamilton and Hare

Best for: Slighter frames and smaller thighs

Best example: Jean-Paul Belmondo in Breathless, perma-cigarette in mouth.

Boxer shorts are the classic sort of underwear worn by classic cinema's husbands – the sort that returned late and thought it sensible to remove their trousers before hat or tie. Yes, loose, baggy, and light has been in favor for decades, and with good reason. However, know that there are a few downsides, too (and not just Don Draper's).

While the cut allows for breathability and the closest thing to natural AC down below, there's a distinct lack of structure. That makes them an uncomfortable companion to closer-fitting trousers, and worse, can cause gathering around the crotch that'll make you walk funny and prompt regular rearrangements (a frown in the company of friends, an employment tribunal in the office).

But! There is good! While boxer shorts don't always lend themselves well to the every day, slimmer guys have less chance to chafe and upset the pants-to-trouser ratio. And, as the providers of cool, cool air, it's the best men's underwear for relaxing, sleeping, and lounging around. We're all doing a lot of that of late.

Uniqlo Woven Boxer Shorts,


Marks & Spencer 3 Pack Cotton Woven Boxers,


Boxer Brief at

Photo by CDLP.

Best brands: Calvin Klein (naturally), CDLP, Versace

Best for: A happy midpoint

Best example: Any CK spread ever.

Not quite the let-loosers of a boxer short, but not as compact as the brief, the boxer brief (you guessed it) gets the formula just right and as such, has become something of a go-to for countless men. It's the forefather to the shorter trunk, too, with more length on the thigh if your legs aren't quite so slim.


What's more the fabric gives it a bit of stretch, which is important for several reasons. Where boxer shorts aren't known for their elasticity, those with more curvature can find them unforgiving. The same for briefs, though where there's stretch, there's so little fabric to actually cover things. The boxer brief gets that just right.

Still, don't think it's a dream ticket. When cut too high, you can suffer the same problem with cuffs interfering with the comfort of your trousers, and when you go too long, it all gets a little bit gastroenterology unit. So again, go mid-length and hit that midpoint equilibrium. If it works for thousands of others, chances are it'll work for you too.

Versace Two Pack Logo Boxer Briefs,

Calvin Klein Pack of 3 Stretch-Cotton Classic-Fit Trunks,


This story originally appeared on Minor edits have been made by the editors.

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