The Best Men's Underwear Is More Important Than Anything Else in Your Wardrobe

·10-min read
Photo credit: FPG
Photo credit: FPG

According to Philip Tierno, professor of microbiology and pathology at New York University, even the best men's underwear isn't built to last. The only things certain in this life are taxes, wrinkles and the death of a lyocell reinforced waistband. And, as the most staple of menswear staples, men's underwear is the hardest worker in your wardrobe. There's a lot of rough and tumble dryer involved. We wear a fresh pair every single day. If you don't, then there are larger issues at hand than the trifling matter of buying decent undercrackers.

They should all be replaced every single year at the very least, too. But to get real mileage from your underwear, it pays to go for quality. That means breathable cotton. Bonus points if it's sustainably produced. That also means no nylon, a fabric that fails to keep everything as fresh and well-ventilated as the cottons used in the best men's underwear. Look, we're not going to explain why that's important.

This lifespan rubbishes the idea of lucky pants then. If you have an anointed pair, you probably won't be 'getting lucky' either – especially if they don't suit the frame DNA (or a Gymbox membership) gave you. Because different pants are built for different guys. It's not just a binary choice of 'normal' and 'model', either. Some pants are better for thicker thighs; others, narrower waists.

Underwear, ultimately, is the foundation upon which the rest of an outfit is built. If you're uncomfortable down there, there's every chance you'll be uncomfortable in the stuff that goes on top. And though you might not be expecting company, you might have company. It's summer after all. So you should care. You should also get a jump on the middling pair of pants that will inevitably land under the Christmas tree at December.

Put it this way: if you feel good, you'll look good – and that sort of confidence is priceless. Lucky pants won't afford you that. A decent pair of the best men's underwear, however, will.

But First, How Do You Take Care of Your Underwear?

Regular washes are essential. But regular washing can ruin clothes. Herein lies the catch 22 of clothing, and underwear, maintenance. The struggle is far less pronounced than that of your favourite hoody, though. You run your underwear through a hot, cleaning wash on the regular, and watch the integrity slowly break down. Or you simply don't wash them as often, keep some shape, and watch your own integrity slowly break down. Look: it's not exactly Sophie's choice is it?

That said, there are some measures you can take to prolong the shelf life of men's underwear. Dialling the temperature down on your washing machine is a start. Heat corrodes fabric density and can set stains into stone. Also, separate those smalls: towels, denim and some lovely organic cotton boxers do not march to the beat of the same machine drum, and fabric friction can cause extra damage.

Don't just chuck them in the tumble dryer either. If you're lucky enough to have a garden or outside space, air drying your underwear is far gentler than a roaring, spinning inferno that spits in the face of your electricity bill. If you've the constitution of an ashamed Victorian, a clothes horse inside will do.

And What Should You Be Looking For?

So we've covered organic cotton. It's breathable, and is grown without a bucket of pesticides, which is always nice. But know that it's not your only option. Some fabrics are better utilised for different situations, too.

"Natural and sustainable fibres such as Tencel are long lasting, and they provide other functions: moisture management, fast drying, lightness and so on," says Claudia Brugger of Hanro's product management division. Since the early 20th century, the brand has made really great nightwear and loungewear with a focus on the classics – which is also an important variable in the big men's underwear debate. "Long-lasting is a word that also applies to the design. Our philosophy: less is more."

Above all else though, Brugger advises that your own comfort should take priority over specific styles or shapes. "Men are usually practical shoppers, so in addition to underwear fitting well, it has to be comfortable to wear, and also easy to maintain. Put the comfort and feel of your underwear above all else."

Few pairs will beat silk in that department. In terms of comfort, there's nothing quite like it – and there's nothing comparable price wise. For silk, expect to pay more, and search more as many underwear brands can still offer top level 'mmmmmm' feelings using cheaper (and often eco-friendlier) fabrics. Plus, it's more susceptible to heat damage and general wear and tear, making it one of the few instances in which 'buy pricey, buy once' is a big fat lie.

Oh, and avoid nylon. There's no breathability whatsoever. It's as natural as a bottle of Mountain Dew. It'll cultivate a fertile promised land for bacteria and infections. And that really is the last thing we need right now. But, thankfully, our edit of the best men's underwear passes all of these checks – and more.


Photo credit: Lululemon
Photo credit: Lululemon

Best brands: CXP, Lululemon, Under Armour

Best for: Guys that don't want a hard, hard workout to ruin their soft, soft shreddies

Best example: Anyone with a Men's Health subscription

A proper workout puts strain upon certain areas of your body that regular day-to-day activity doesn't hit. That's the point. But most men's underwear is designed purely, and solely, for the day-to-day. Soft cotton seams aren't built for muscle trembling squats. Worse still, any sort of rigorous cardio can elicit the sort of chafing that'll bring a whole new level of soreness to your recovery period.

CXP's founder Tom Austin began to formulate a balm. "We've had experiences of working with Premier League players who were getting Primark underwear from the kit man. They suffered mid-game chafing and broken skin – incredible when you consider the innovation involved with team strips and boots," he says. "Sports specific underwear such as CXP is specifically designed to improve sports performance by actively supporting key areas which ordinary underwear doesn’t do."

Austin knows what makes for sound workout men's underwear, then. One: you should be able to move freely. Obvious enough. But it should also be intuitive. "[The underwear] should move with, not against, your body. So go for seamless construction, compact waistbands and also consider inseam length and which garment shape works best for your specific workout or sport."


Photo credit: American Apparel
Photo credit: 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 minimised 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.

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.


Photo credit: CDLP
Photo credit: 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 artefact 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). In 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.


Photo credit: UGC
Photo credit: UGC

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 favour 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 everyday, 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.


Photo credit: CDLP
Photo credit: 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.

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