Lucky underwear is not A Thing. There are pants and briefs and boxers we can call our 'best underwear', sure, but that has nothing to do with luck. And, chances are, if you deify one pair to be some sort of talisman, you won't be getting 'lucky' either. This is not American Pie.
Instead, you should think of your underwear as the foundation around which you build the rest of your outfits. Sure, it might not be seen. But then again, it might. So you should care about your smalls as much as you care about everything else you wear. That means no buy-one-get-fourteen-free multipacks. And it also means buying it for yourself, rather than waiting for someone else to do it for you at Christmas or birthdays.
As things like smart sweatpants lead us into the looser, cosier corners of menswear in These Unprecedented Times, you want – no, need – to be comfortable, and the Calvin Kleins gifted from your ex shouldn't be the only options in the drawer. Especially if you're not a Calvin Klein model. Just as we're not all built like minor Greek demigods (...right?), it makes sense that different underwear suits different body types.
But what links all the best men's underwear is a few core tenants: breathable fabrics are preferable to organ-cooking synthetics; the elastic shouldn't snap upon its first pull. Other than that, it's a case of identifying your body shape, and building an underwear drawer that best suits you.
You'll look better. You'll feel better as a result, and that sort of confidence is quite important when you're entertaining company in your underwear. If you really want to get lucky, read on below.
OPTION #1: THE TRUNKS
Best brands: Hanro, Derek Rose, CDLP
Best for: Slighter frames, or trimmer frames, or both
Best example: Shawn Mendes in That Ad Campaign which caused adolescence as we know it to implode.
Not to be confused with the hybridous boxer-brief (more of which later), trunks are arguably the newest – and most comfortable – development in the world of men's underwear. They look a lot like other options too: they've the snugness of a brief, the shape of a boxer and the best-of-both-worlds of the boxer-brief. But what separates trunks is the leg length: this sits just below that crease where thigh meets pelvis, hence, trunks.
Okay, that sounds very uncomfortable and chafing. Though in reality, trunks are specifically designed for comfort. Where skinnier legs suffer ruching, pooling fabrics from underwear that won't quite behave under jeans or trousers, trunks have minimised that risk altogether. And, with a cut-off at the widest point of the thigh, they can make your legs look less yeah-I-only-do-leg-day-once-a-month, and more yeah-I-can-crush-a-watermelon-with-these-thighs-and-what-of-it.
If you're not sold on that (and you should be), know that trunks, generally speaking, involve a lower rise waistband too. That means no pants being twisted by a tighter-than-usual pair of trousers, and more exposure to the Adonis abs you've no doubt gleaned in lockdown.
OPTION #2: THE BRIEF
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 #3: THE BOXER
Best brands: Sunspel, M&S, Hamilton and Hare
Best for: Slighter frames and smaller thighs
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 #4: THE BOXER BRIEF
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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