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 per cent cotton in either a solid colour 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.
Boxer-briefs
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
