The Style-Conscious Man’s Guide To Underwear

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

And, it’s not just in case you get lucky or hit by a bus that you should pay attention to what lies beneath. Compiling the perfect men’s 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 undies in check. And funnily enough, it turns out that your mum doesn’t know best. At least not when it comes to this.

Different Men’s Underwear Styles

Of all the seminal moments in a man’s life – graduations, weddings, having a child – none means more than the first time he chooses his own men’s 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.

Briefs

“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,” Francis says.

“[Look for] a modern, tailored cut that is much more flattering and works well with slimmer leg-wear. This means they will complement any body shape, being both flattering and extremely comfortable.” Men's Boxer Shorts

Trunks

“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

Athletic

“If you’ve ever tried to run in baggy boxers, we sympathize. 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

Best Men’s Underwear

Calvin Klein

You don’t need us to tell you that Calvin Klein is the daddy of all men’s 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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Men's Underwear - Calvin Klein
Image Credit: Calvin Klein

Ron Dorff

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

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Men's Underwear - Ron Dorff
Image Credit: Ron Dorff

Marks and Spencer

Marks and Spencer used to be the place your grandad would head for men’s 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 colors and patterns. Move over gramps.

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Men's Underwear - Marks and Spencer
Image Credit: Marks and Spencer

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 men’s underwear range is all paisley, stripes, cotton, and (compulsively stroke-able) silk. Consider it the Rolls Royce luxury of the underwear world.

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Men's Underwear - Derek Rose
Image Credit: Derek Rose

Under Armour

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

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Men's Underwear - Under Armour
Image Credit: Under Armour

Sunspel

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.

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Men's Underwear - Sunspel
Image Credit: Sunspel

Uniqlo

Buying men’s 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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Men's Underwear - Uniqlo
Image Credit: Uniqlo

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 funneled all of his on-court underwear-related woes into his own range of performance underpants. Expect scientific-sounding design features and drier wear during sports.

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Men's Underwear - Bjorn Borg
Image Credit: Bjorn Borg

Hamilton And Hare

Hamilton and Hare may sound like an esteemed member of the club Savile Row, but in fact, this brand is dedicated to the craft of doing underwear for men the justice it deserves. With an 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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Men's Underwear - Hamilton and Hare
Image Credit: Hamilton and Hare

Hanro

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 underpants.

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Men's Underwear - Hanro
Image Credit: Hanro

Men’s Underwear Buying Guide: The Best 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.

Cotton

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

Jersey

It’s soft and lightweight with a natural stretch, making it the perfect choice for guys on the move. The Sunspel team advises 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 the traditional jersey. “We use a natural paint nanofiber and blend it with cotton for a luxurious feel – the microscopic nanofibers offer unparalleled smoothness as well as moisture absorption.”

Silk

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.

Mesh

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.

Marky Mark Calvin Klein Men's Underwear Ad
Mark Wahlberg Calvin Klein Ad

Men’s Underwear Rules

1. Clear Your Drawers Out Regularly

Even if you buy the best underwear for men and treat them well, 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.

2. Pick Your Fabrics Wisely

In most cases, cotton underwear is a great option because it’s natural, breathable an,d 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 gym wear and won’t need to be wrung out after you’ve achieved a PB on leg day.

3. Size Yourself Up Properly

For reasons which we won’t go into, trying on men’s 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 that 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.

4. 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 men’s 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.

5. 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.

Harry Rowley

How To Wash Men’s Underwear

“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.”

Wash: “Obviously never mix whites with greys, off-whites or colors 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.”

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.”

Men's Underwear - Hamilton and Hare
Image Credit: Hamilton and Hare

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 recognizable men’s 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 for men front and center (thanks in no small part to Calvin Klein and Marky Mark) with who you were wearing becoming just as important as what shape of men’s underwear 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.



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