The Best Men's Underwear Guide You'll Ever Read

Unless you’re a) David Gandy or b) one of those guys who has to take it too far by stripping off on a night out, your underwear is not for public consumption. However, that doesn’t mean you’ve got licence to wear the living daylights out of whatever overstretched, greying grundies that you can get your mitts on. Underwear matters.

And, it’s not just incase you get lucky or hit by a bus that you should pay attention to what lies beneath. Compiling the perfect underwear line-up will do wonders for how you feel in your clothes and will soon put a stop to your boxers getting funny ideas about moving far further northwards than your trousers.

To make sure your underwear etiquette is on point, we’ve put together absolutely everything you need to know about getting your kecks in check. And funnily enough, it turns out that your mum doesn’t know best.

A Brief History Of Men’s Underwear

The first record of anything resembling underwear dates back to around 7,000 years ago and takes the form of Ancient Egypt’s loin cloth: a strip of fabric wound and fastened around its wearer’s delicates. Basically, an adult nappy.

It wasn’t until around the 13th century that more recognisable underwear made an appearance, with slip-on loose undershorts that ended at the calf becoming a social non-negotiable. The Renaissance stepped up underwear’s sex appeal a gear by going tighter and shorter (only knee length, mind), while the period’s introduction of a urination flap which could be opened at a moment’s notice turned out to be one of mankind’s greatest inventions, ever.

The following centuries witnessed little change (give or take an inch or two at the hem or fabric choice) until the 1930s when briefs appeared, challenging short-style underwear’s monopoly on modesty preservation. For the rest of the 20th century men drew battle lines between boxers and briefs, with the boxer brief born out of a desire to unite men everywhere – it didn’t work.

There’s another plot twist too. While the best way to package one’s privates was a personal matter through history, the late 1980s and early 1990s put underwear front and centre (thanks in no small part to Calvin Klein and Marky Mark) with who you were wearing becoming just as important as what shape of undercrackers that you professed loyalty to.

That brings us to today, a time where the squabble between brief and boxer lovers still rages on and a time where everyone can agree that the letters on your elasticated waistband matter, a lot.

Marky Mark Calvin Klein Underwear AdMarky Mark Calvin Klein Ad

How To Pick An Underwear Style

Of all the seminal moments in a man’s life – graduations, weddings, the first curled fist of your child around your little finger – none means more than the first time he chooses his own underwear.

But what worked for prepubescent you isn’t your best choice now. Your body’s changed. Your needs have changed. Somewhere there’s a fit that’s more snug. More supportive. More flattering. Let Olivia Francis, founder of underwear experts Hamilton & Hare, be your guide to buying pants that are anything but.


“This is the traditional Y front. It’s not for everyone but it offers great support and a neat fit. Particularly good for men with large thighs.” Men's Briefs/Y-Fronts

Boxer Shorts

“Traditional boxer shorts offer maximum coverage, comfort and breathability but can often bunch and ride up so do not work well with slim trousers. [Look for] a modern, tailored cut that is much more flattering and works well with slimmer legwear. This means they will complement any body shape, being both flattering and extremely comfortable.” Men's Boxer Shorts


“These are a newer style and offer the simplest silhouette, ideal for wearing under slim-fit trousers. They sit perfectly on the hip, a little lower than other styles, and are short in the leg, cutting across mid-thigh, which make them best for men with skinnier legs.”

Take care with ‘hipster’ styles, warn the experts at M&S; they sit low, so work best with tucked in shirts. Or you risk an intimate breeze every time you bend down. Men's Trunks

Boxer Briefs

“These are a hybrid between the traditional boxer short and the trunk – they sit on the waist and are slightly longer in the leg. Universally flattering and versatile, they’re the go-to option for most. Particularly good for those with fuller buttocks.” Men's Boxer Briefs


“If you’ve ever tried to run in baggy boxers, we sympathise. Athletic underwear comes with special requirements – it has to keep you in place and be breathable enough to cope with sweaty gym sessions.” Men's Athletic Underwear

The Right Underwear Fabric

Three things matter in your most intimate wear: comfort, support and breathability. Underwear brands have long defaulted to cotton and jersey, which provide all three. But textile innovation offers the modern man new ways to keep himself cool and dry.


An old classic. “This is a brilliant fibre for underwear,” says Francis. “It’s naturally breathable, soft and hypoallergenic.”


It’s soft and lightweight with a natural stretch, making it the perfect choice for guys on the move. The Sunspel team advise to “opt for a stretch style, with higher elastic content for added support if you spend your weekends exercising as opposed to relaxing.”

Lyocell Jersey

Hamilton & Hare developed this exclusive spin on traditional jersey. “We use a natural paint nanofibre and blend it with cotton for a luxurious feel – the microscopic nanofibres offer unparalleled smoothness as well as moisture absorption.”


It’s a classic choice, but silk is quickly disappearing from the underwear market. And for good reason. “Although it offers incredible lightness and breathability, it’s a delicate fabric that doesn’t benefit from wash and wear and damages easily,” says Francis. Leave to Peter Stringfellow.


The go-to material for sports-oriented underwear, mesh is light and breathable. Some brands go even further and use heat-sensitive mesh fabric that helps disperse body heat and leaves your pants feeling cool to the touch – even after a bout of cardio.

The Other ‘Underwear’ You Need To Know

These days, underwear is about more than just pants. Here’s everything else you should slip between skin and clothes.


This isn’t necessary all the time, but an undershirt prevents sweat stains and means your dress shirts need washing less so last longer.

Go for a V-neck – few things kill your look like a crew neck behind an open collar – in breathable cotton. Look for tight fits in light to mid grey – it’s less visible under a white shirt than white. Vests also create visible lines on your shoulders, so stick to T-shirts.

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White socks are streetwear’s current obsession, but if you’re not in a hoodie, stick to classic black or navy. Your socks should be long enough to show no skin when you cross your legs, unless you’re after mankles. In which case, invisible socks let you flash yours without stinking out your shoes.

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Underwear Rules

Clear Your Drawers Out Regularly

No matter how well you treat your underwear, eventually those tighty whities will turn to grubby grundies. Make sure that you have a regular check-in with your collection of underwear (about every three months or so) and dispose of anything that you’d be embarrassed to be seen in by a significant other.

Pick Your Fabrics Wisely

In most cases, cotton underwear is a great option because it’s natural, breathable and will absorb a degree of unwanted moisture down below – it’s basically your best bet for every day. But if you’re exerting yourself, things get a little more, ahem, steamy, so you’ll need to look for fabrics that bolster cotton’s natural assets by wicking away moisture. A cotton-spandex blend is ideal for gymwear and won’t need to be wringed out after you’ve achieved a PB on leg day.

Size Yourself Up Properly

For reasons which we won’t go into, trying on underwear in shops isn’t good form. Having an awareness of your core size and sticking to a certain brand when you’ve found the perfect fit is crucial for comfort, however.

Underwear which comes up too large will have you shifting around in your seat all day, while anything that’s smaller than it should be will cut off your circulation rather than boost your package. Size matters.

Description of imageDavid Gandy for M&S Autograph

Wash White Underwear In Non-Chlorine Bleach

If you think you’ve mastered the art of being a grown up because you’ve figured out that bleaching white underwear will stop it looking from so goddamn tired, you’re actually only an adulthood amateur.

Bleach will restore some of the former glory of your white underwear, but you’ll need to make sure it’s a non-chlorine variety to reap that dazzling brightness without wreaking havoc on your underwear’s elasticity.

Buy Little And Often

Relying on the charity of others (usually at Christmas) is a surefire way to put unnecessary strain on the smalls which live in your underwear drawer. To make sure that all your underwear gets a regular break, make sure that you’re getting into the habit of topping it up on the regular.

This way your pants won’t suffer from premature ageing and if you’re naff at remembering to stick on a regular wash, you’re less likely to encounter an empty drawer and face a day going commando.

How To Keep Your Underwear Looking Good

You’re not Bridget Jones, so you’ve no excuse for grey, saggy pants. Even if no one’s going to see them. “Keeping your underwear in pristine condition means taking extra care,” advises the Sunspel team, “so be as gentle as possible when washing, folding or ironing – if you’re way that way inclined.”

Wash: “Obviously never mix whites with greys, off-whites or colours as they will lose their sheen. Temperature is key too – a hotter wash does more damage to the fabric, so stick to 30 degrees and, if possible, use a gentle wash cycle. Silk, because of its delicacy, should always be hand-washed.”

One option: Only buy black or navy pants. That way, you can chuck them in with your darks.

Dry: “Drying your underwear flat means they keep their shape better. Due to their delicate nature, it’s best to avoid a dryer.”

Storage: “If you’re keen to go the extra mile you can fold your underwear in tissue paper to preserve the fabric and keep it neat and unwrinkled. Another tip is to store garments with lavender or cedar wood – the scent will deter moths.”

Best Men’s Underwear Brands

Calvin Klein

You don’t need us to tell you that Calvin Klein is the daddy of all underwear brands, but we’re going to tell you anyway. Ever since that not-so-subtle branded waistband graced the hips of Marky Mark, the sight of a pair of snug Calvins has become sartorial shorthand for ‘man who’s serious about his undercrackers’.

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Ron Dorff

Ron Dorff’s statement of intent is ‘Swedish functionality with French style’. Mercifully, that’s delivered through its unflashy, well-made underwear range. Fabric covered waistbands, discreet design and crowd-pleasing colours make this brand the Apple of the underwear world: plenty of brains and no shortage of beauty.

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Marks And Spencer

Marks and Spencer used to be the place your grandad would head for underwear that did the job and not much else. Today, though, Marks and Spencer’s underwear designs combine a wallet-friendly price tag with a surprisingly comprehensive range of colours and patterns. Move over gramps.

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Derek Rose

Fancy slipping into something a bit, um, silkier? Derek Rose should be your first port of call. Wearing its incredibly indulgent credentials like a badge of honor, the brand’s underwear range is all paisley, stripes, cotton and (compulsively strokable) silk. Consider it the Rolls Royce of the pants world.

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Under Armour

Forget designer name-dropping waistbands and overpowering prints, Under Armour underwear is the sensible man’s privates coverer of choice. Perfect for keeping you cool down below thanks to anti-odour and sweat-wicking technology, when wearing a pair you can kiss goodbye to saddle sweat.

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British brand Sunspel has built a – well deserved – reputation for producing the comfiest T-shirts of all time, so readers, try imagining that feeling of soft cotton on your nether regions. Luckily, you don’t have to long for softness, lightness and comfort any longer, because Sunspel’s underwear offering has got all that and more ticked off.



Buying underwear ain’t cheap. That’s why we’re unapologetic fanboys of Uniqlo’s wallet- and wang-friendly designs, which prove that you don’t have to be wadded to get your briefs in check.

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Björn Borg

Widely considered to be one of the greatest tennis players of all time (and owner of one of the most Swedish-sounding names of all time) Björn Borg thankfully funnelled all of his on court underwear-related woes into his own range of performance pants. Expect scientific-sounding design features and a drier wear during sports.

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Hamilton And Hare

Hamilton and Hare may sound like an esteemed member of club Savile Row, but in fact this brand is dedicated to the craft of doing underwear the justice it deserves. With obsessive focus on fabric, fit and design, the label’s offering will ensure that your first layer is so much more than a mere panic purchase.

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If you’ve spent your life receiving emergency underwear packages from your mum every Christmas, it’s time to treat yo’ self. Hanro’s line-up of boxers and briefs are all quiet luxury, discreet prints and unbelievable comfort – in a nutshell, they’re scientifically perfect pants.

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How To Look Good In Just Your Pants

Male model Harry Rowley, from agency Models 1, has stripped off for Ralph Lauren, Emporio Armani and Fucking Young! magazine. Here, he reveals the secrets to looking good in next to nothing.

Harry Rowley

I used to find underwear shoots nerve-racking. You don’t really know the photographer and you’ve got to familiarise yourself with the situation, but once you relax and settle into it, it becomes just as easy as general modelling. Once you’re forced into these uncomfortable situations time and time again you get used to meeting strangers and stripping off in front of them; it becomes normal in a way.

It’s always good to pump yourself up before a shoot – it just gives you that extra confidence in yourself. You don’t want to overdo it, but a set of push-ups and a few crunches are always going to help.

Ultimately, the key to looking good in your pants is posture. If you’re not standing up straight with your shoulders back, your abs aren’t going to be looking good. Underwear modelling is all about physique, so slouching won’t do your figure any favours.

Personally, I find boxer briefs most flattering – they’re a better fit for me, and they’re not quite as tight as Y-fronts. I tend to wear a lot of Armani underwear – it looks good and it’s comfortable.”

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