Mid-life crisis or nirvana for a gentleman’s tackle? We road test the sexiest underpants in the world from Tom Ford…

Here’s a question that Aristotle never had to wrestle with: at what point in life does a man become conscious of the aesthetic potency of his underpants?

Early on our pants are a protective barrier between harsh reality (the grubby, wider world and all its germs and gazes) and us. When one is very young, undergarments should be all function and zero stylistic affectation (save a few embroidered bunnies). Between the ages of five and 10 my manhood was snugly nestled in a pair of wholesome Yfronts, briefs originally invented in 1935 by Chicago designer Arthur Kneibler. Those early-learning loose cotton briefs in navy blue, burgundy and charcoal (from Marks & Spencer, natch) came in packs of five, each tightly rolled like a wedge of stolen banknotes. Even though I was, thankfully, growing in all nooks and corners of my pale body, the need for ‘support’ was minimal even when, say, trampolining.

Then 1992 happened. The very same year I became a teenager, Marky Mark swaggered into view on the back of my mother’s Vogue and changed the way boys wore their pants. Seeing Wahlberg in the Calvin Klein adverts, wearing a backward-facing baseball cap and a pair of pristine white boxers was, for me, nothing short of a Damascene conversion. Suddenly I became all too aware of my underwear’s basicness. Grabbing his junk with his right hand like he was squeezing two ripe oranges, his top lip curled provocatively, Marky was an icon of red-blooded masculinity. A modern he-man in some seriously good pants. My appearance wasn’t quite so chiselled.

Still, if I couldn’t have a body like him, at least I could buy the merch. Every kid in my class wore Calvin Klein boxers with unabashed pride, ensuring that the waistband (printed in the brand’s famous ‘Futura’ font) peeped out of the top of their too-baggy Duffer of Saint George jeans. In hindsight, I can see that it was my first attempt at peacocking: wearing an item of clothing that would project my teenage virility. The dandies of Beau Brummell’s era had britches and pussy bows; us Nineties skate kids had branded pants and Motorola pagers.

Fast forward to 2018, however, and I’m beginning to realise that, as a man in his late 30s, I can’t wear the things I used to at 21. If I do, those closest to me, including my girlfriend, will mock me relentlessly. At this age my denim should be narrow, rather than skinny; my hair should be styled, but not stiff with product; and my underpants sexy but not too visible outside of those opportune moments when they are seen and then shed. I’m not fat — I run and swim, but when I look in the mirror I don’t see a thirst trap. So, what to wear to make me feel a million bucks inside the bedroom and out? What sort of bow can you wrap around the package to make it more appealing?

There’s only one man who can add sex and refinement to such a serious fashion conundrum and that’s American designer Tom Ford. This summer saw the launch of his first men’s underwear range and I decided to see if the impeccably groomed designer’s vibe would rub off on an overworked father of two looking to up his underwear game. I’ll be honest: before trying them on — the parcel I received comprised six pairs of pants, four pairs of boxer shorts (in silk!), one pair of grey traditional briefs and one cotton trunk brief — I was more than a little sceptical. I was less intimidated by the briefs and the Y-fronts as they were more like my regular underpantage. No, what held my attention were the silk boxer shorts — in metallic gold, midnight blue, whipped-cream white and, oh yes, zebra print, all with black velvet elastic across the top.

Surely I couldn’t get away with these? Standing naked in the bathroom, holding up the soft silk squares, it seemed absurd that I was considering such a move. Who did I think I was? David Gandy? Peter Stringfellow? Yet when I pulled them on my worries fell away. It was as if my particulars had been placed on a pillow of nothingness. Gone was the feeling one usually gets when one stuffs one’s crown jewels into a tight pair of cotton boxers. Gone were the moments where you look like a man who’s got a lobster caught where he shouldn’t have; gone was all the pushing and pulling to get the various lumps and bumps sitting comfortably. In Ford’s silken heaven there was no jostling for space, no re-ordering, no pinching. Mid-week I took my silk numbers swimming at Marshall Street baths in Soho. (I was once a member member of the Bulgari pool in Knightsbridge, but I kept bumping into famous people I’d interrogated in my day job.

There’s nothing like being admonished by a butt-naked A-list actor, his tackle waving in the wind as he polishes off a whey protein shake. No wonder they say it’s rude to point). Marshall Street pool is always full of testosterone. If the Tom Ford pants can win hearts here, he’s onto something. I wore the zebra print and, although some may have mistaken them for swimming trunks, I do believe a couple of the looks I got were downright envious. Nothing signals ‘kind of a big deal’ quite like animal stripes on your nether regions. So, what would my girlfriend think? Well, I wore the boxers one Friday night but in the interests of decency I won’t go into further detail. It did, however, feel good to be dressing up for her for a change.

If Tom Ford’s pants have taught me anything it’s that one shouldn’t rest on one’s laurels, especially if said laurels are a pair of old Y-fronts won in a Christmas raffle. Sure, silk might feel a little silly for some British men, but what better way to get her (or him) into bed than a chuckle at the ostentatiousness of it all? From here on, I’ll only be wearing silk. Everything else is just pants.

Jonathan Heaf is features director of British ‘GQ’.

Photographs by Elliott Morgan.

Grooming by James Oxley using Wella Professional.

Photographed in a Bulgari Suit at Bulgari Hotel London.