The Best Men's Underwear Guide on the Internet

·12-min read
Photo credit: NBC
Photo credit: NBC

Honeymoon periods, episodes of Succession, and the best men's underwear: three good things that, sadly, all come to an end at some point. The latter is particularly painful. Because, with so many styles on offer, and with so many brands vying for our attention, finally stumbling upon the perfect pair can feel like coming home. It just feels right. So when they eventually begin to fray, and crumble, and develop holes in all the wrong places, there's always the temptation to hang on. Everything will work out in the end. You're supposed to be together!

Except you're not, says NYU's professor of microbiology and pathology, Philip Tierno. Speaking to The Huffington Post, the professional germ master stated that even the best men's underwear can become a cradle of filth. Thus, they should enjoy a life cycle of just 365 days.

That said, some of the best men's underwear can live a little longer – and if you invest wisely, they'll have a happier life too. As will you. Find a pair that's specially designed for your body and/or lifestyle, and there's every reason to believe that you'll look even better in them. Just as different suits are made for different builds, so too is the best men's underwear. It's not just a binary choice of 'normal' and 'model', either (though most of us obviously, definitely, absolutely fall into the latter camp). Some pants are better for thicker thighs; others, narrower waists. Gym rats will need underwear with more stretch. Those with the abs of a Fight Club Brad Pitt will want to show them off with a lower waistband. Those wanting ultimate comfort will need some loose boxer shorts. You get the picture.

It's also worth thinking about the trials and tribulations the average bit of underwear faces. There's a lot of rough and tumble dryer. Which means excessive washing. Which means a lot of heat. Which means a construction that is routinely compromised since we put on a fresh pair of men's underwear with each passing morning. (If you don't, then you're a disgrace).

To get real mileage though, it pays to go for quality; the good pants without the novelty print, and ones that don't shine under bright lights. 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 (the shiny stuff we were talking about). We are not going to explain why it's essential to keep things airy down there.

Underwear 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. You'll be walking funny for a start. So, you should care. You should make the effort. You should also get a jump on the middling pair of pants that will inevitably land under the Christmas tree at December (thanks mum).

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?

Men's underwear needs washing. It really does. But too much washing can ruin your men's underwear. So what gives? As the experts have long argued, men's underwear isn't built to last forever. It's not a hoody you've had since university. Nor is it the same as your favourite go-to suit. Underwear takes a regular beating at hot temperatures – both in and out of the washing machine – and cotton ultimately breaks down with so much use. When a waistband starts coming away, prepare to bid farewell.

There are ways to extend the lifespan, though. Dialling the heat of your washing machine can work, and 40 degree washes are just as good as cleaning clothes (unless there are some stains, and if that's the case, they should be thrown out completely). Know that underwear should be washed with likeminded kit. It might be more convenient to bang in your smalls, towels and denim all at once, but the fabric friction can cause damage to weaker materials – and the lovely organic cotton of your brand new boxer shorts are some of the weakest in the drum.

Then, when that's all done, eschew the tumble dyer. Air drying either outside or on a clothes horse is a much gentler alternative to a spinning, angry, red hot barrel (and your utility bill too). Plus, there's always that fresh smell the nice lady on advert gets when she buries her grinning face into clean, dry laundry, because that's a totally normal thing to 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.

OPTION #1: THE WORKOUT UNDERWEAR

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."


OPTION #2: THE TRUNKS

Photo credit: American Apparel
Photo credit: American Apparel

Best brands: Hanro, Falke, CDLP

Best for: Slighter frames, or trimmer frames, or both. Trunks can work for most guys, to be honest

Best example: Shawn Mendes in that sweltering Calvin Klein ad

Don't get trunks confused with boxer briefs. We'll get to that in due course. These particular pants are arguably the best men's underwear because they combine the finest parts of its compatriots. There's all the compact, flattering snugness of the brief. There's the shape of a boxer, which is a little more modern. But, ultimately, trunks are engineered to slip right under your clothes.

You can thank the leg length. In the underwearld, trunks (like the swimwear) finish just below the crease where thigh meets pelvis. No more fabric riding up, but not quite super tighty whities either.

That means you can wear jeans, chinos, shorts, whatever, and you can do so without fear of chafing – a lot of which can happen during the clammier, grosser, warmer months. Trunks will make your legs look good, too. By cutting off at the widest possible point on the thigh, there's an illusion of a bigger, meatier leg no matter how heavy you squat (or not).

Still unsure? Don't worry. Stick with us. Trunks, generally speaking, offer a lower rise waistband. So where fabric eschews twisting and discomfort down below, trunks offer the same luxury at waist height. Plus, it's another way to flatter the perfect abs you've no doubt farmed in lockdown.

OPTION #3: THE BRIEF

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.

OPTION #4: THE BOXER

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.

OPTION #5: THE BOXER BRIEF

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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