Considering they’re the first thing you slip into every day, underwear is probably the last item in your wardrobe you put the time into researching. It’s worth doing so. Getting the right pair in your armory not only means you'll feel better all day, but your clothes will hang better too.
The most important thing to remember when buying underwear is to be honest with yourself. This is the layer that sits closest to your skin, so if it doesn’t feel good, it’s time to edit. There are also clear signs that you might be wearing the wrong size altogether. If the leg bands dig into your thighs, you’re probably wearing a size too small. If your waistband keeps slipping every time you bend over, you're either wearing a size too big or the elastic has gone (and it’s time to have a throwout).
Here, we break down the four major cuts and the men they look best on.
Best for: men with larger thighs (and those who are, ahem, more well-endowed)
Forget those briefs your mother used to buy you, the new generation of designer styles on the market are sleeker and more stereotype-breaking than ever. And there’s a reason you’ve seen footballers who put in the legwork, such as David Beckham and Cristiano Ronaldo wearing them in campaigns: they’re the best choice for guys with bigger thighs. If you’re repping thicker trunks, you’ll find underwear with legs tends to ride up during the day, causing a roll in the material that will show through slim-fitting trousers.
Briefs are also good for shorter guys, as they expose more of your legs, making them appear longer and you, therefore, taller.
Perhaps most importantly, this style is superbly supportive – ideal if you’re a cardio fiend. For day-to-day dressing, we recommend going for a 100 percent cotton pair, but look out for versions in a technical fabric for workouts, as these will wick away moisture from your skin. No man-made fibers, unless you’re particularly keen on getting a rash down there.
One thing to bear in mind is that different labels cut leg holes at different angles. And just like the armholes on a Savile Row suit, this can affect the way they fit. A slimmer section of material underneath the waistband usually means less material at the back of the pants themselves, so these are more suited to guys with smaller posteriors (or one that’s continually being tightened up at the gym). If you are blessed with something larger back there, look out for briefs with slightly more material above the thigh area for more coverage behind.
Avoid those uber-trad Y-fronts that sit below the belly button. No prospective date wants to be reminded of their grandpa when you strip off for the night. For us, Tommy Hilfiger does briefs expertly, providing just the right amount of cuffing to the nether regions, without being too restrictive.
Best for: maximum breathability
If you’re not the kind of man who regularly wears suit trousers or slim jeans, boxer shorts offer the greatest breathability and are far less revealing than any other style. However, that comes at a cost: boxers offer very little support.
Although you probably first wore these in your teens as a rebellion against the tighty-whities you'd been forced to wear before, this is another style of underwear that has had a gentlemanly makeover in the past few years. The baggy cut and bunched, elasticated waist might be the most traditional version, but plenty of designers now offer shorter, slimmer-cut options with a stretch band waist, which are a viable option for men with slim thighs.
As a side note, if you’re a man with more substantial thighs that tend to touch when you walk, boxers can be tricky: the low cut of the crotch often means your junk gets caught in the crossfire, so to speak. And if you’re wearing trousers, this can get sweaty and potentially quite sore.
However, this style’s breathability means they are the best choice for sleepwear – go for a pair in 100 percent cotton in either a solid color or a cool pattern with a trim, tailored waistband.
Helpful hint: if you’re in seduction mode, avoid novelty Christmas pants at all costs. Sunspel do a cracking pair, which are floaty and will give you just enough breeze.
Best for taller men (and guys with an ample posterior)
As implied by the name, boxer-briefs have the shape of traditional boxer shorts, but cut from more fitted jersey material. Since the rise of slimmer silhouettes in menswear over the past decade or so, this has become to go-to style for most guys. Arguably, it is the most versatile style out there: not as revealing as briefs, but offering all the support with added thigh-skimming powers.
Boxer-briefs usually hit the mid- to low-thigh and often have a button fly. This means they can also be a great additional style, alongside briefs, for men with larger thighs – and the added material between your legs means it can help avoid any rubbing or chafing. That said, if that’s your goal, be sure to choose your pair wisely: go for the longer length and make sure they’re not too tight or they will bunch up under your trousers.
Boxer-briefs really come into their own for men who have more to store back there. Those with larger posteriors often find briefs don’t provide enough coverage and in order to get boxers that fit over the thigh-and-bum area, the waistband ends up being too loose. With close-fitting fabric that stretches over your legs, boxer-briefs offer the perfect halfway house.
Although this is a versatile style that will suit most men, a higher waistband is usually a key component of boxer-briefs, which makes them especially good for taller frames, on whom underwear can slip down when bending over. Hugo Boss' boxer-briefs are a wardrobe staple for us, bridging the gap between too short and too long.
Trunks and hipsters
Best for slimmer men or gym-honed guys
The newest style on this list, trunks are a shorter version of the boxer-brief and have grown in popularity with the rise of super-skinny trouser styles over the past five years or so. When it comes to length, they tend to sit from the mid- to upper-thigh. Some come with a keyhole fly, but usually, the style is flat-fronted and sometimes includes an extra pouch of fabric for added support and... "enhancement".
As this style fits more flush to the skin than boxer-briefs, often with a higher degree of stretch in the fabric, this style is best worn by men who are slimmer of thigh – anyone with larger thighs may find the pant legs ride up when you walk.
Another advantage for guys with slimmer legs is that their tight fit means trunks will not leave a bunch of excess fabric around your thighs, making them appear thinner. Look out for a pair that bisects your thigh at its widest point, as this will emphasize that width and make your legs look more muscular.
This style also usually has a lower waistline than its boxer-brief counterpart, meaning they sit lower on the hips: especially good if you’ve been putting in the hours on that eight-pack.
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