History in briefs

Are you a Churchill, a Cousteau, a Hemingway — or a Wallace? Find out with Esquire’s only slightly sketchy Icons in Their Underwear wallchart

Boxer briefs

Neil Armstrong

The original Captain America, Armstrong needed reliable kecks; something that wouldn’t ride up during the launch sequence or perish 240,000 miles above Earth. Sleek and understated, but with the capacity to impress the lunar babes, were they to materialise. A bit like Armstrong himself.

Today he’d wear: The Sea Island pant, £102, by Zimmerli. Classic and hardwearing in ultra-luxurious Sea Island cotton.

Y-fronts

Ernest Hemingway

“There are some things which cannot be learned quickly, and time, which is all we have, must be paid heavily for their acquiring.” We don’t know for sure he was talking about underpants in Death in

the Afternoon from 1932, but Y-fronts are especially good for bullfighting, so he probably was.

Today he’d wear: Lyocell-elastane Y-Briefs, £27, by CDLP. Complete with a macho “enhanced pouch” and even odour-resistance.

Briefs

Jacques Cousteau

Alongside red beanies and silver wetsuits, classic budgie smugglers were standard issue uniform aboard Cousteau’s research vessel Calypso. The French oceanographer would often stalk its decks — Gauloise on the go — in just his pants, surveying the horizon, ready to scuba-tank-up at a moment’s notice.

Today he’d wear: Cotton Karl Heinz briefs, (three pack) £70, by Schiesser. Fitted and sleek, ideal for skinny jeans and sportswear.

Boxer shorts

Muhammad Ali

Pretty self-explanatory but The Greatest was a real stickler for loose underwear. In fact, Ali was so in thrall to its comfort that he would layer up, often wearing six or seven pairs beneath his boxing shorts: perhaps the true secret of his power.

Today he’d wear: Pure twill cotton boxer shorts, £35, by Hamilton & Hare. English tailored boxers which have to pass a facial-skin softness “cheek test” before being allowed on sale.

Silk boxers

Sir Winston Churchill

After a hard day battling the Nazis, Winnie would retire to Number 10, slip out of his Turnbull & Asser one-piece “siren suit” and into a bath. An hour later and toweldried, he’d reach for the silky bloomers and a Romeo y Julieta before sitting by the fire and dozing off.

Today he’d wear: Silk-satin Brindisi print boxer shorts, £150, by Derek Rose. Super lightweight and soft on your body’s CBD, but perhaps best reserved for those bigger occasions.

Commando

William Wallace

As the great aggravator might once have said, “They may take our lives, but they will never take our freedom (to not wear pants!)” He had a point: nothing’s going to spur you on in battle like the whip of a Highland gale about your knackers.