As the name implies, it’s the boxer short that, historically, has had a touch of machismo about it. Back in 1925 one
Jacob Golomb, founder of the Everlast sports company, created a lightweight, elastic-waisted style of shorts for
boxers to fight in. The style caught on for everyday wear, not least because men’s underwear up until that point was
typically bulky, onesie-like and woolen. Indeed, men demonstrating that they had an active interest in their
underwear sparked development. Some nine years later the brief style of underwear was launched by an underwear
manufacturer called Cooper - previously inventors of the first male underwear with a front opening. They called
their new model Jockey briefs. Its big selling point? Less the new Y-shaped opening, as the fact that it offered
what it called “masculine support”. You know what they mean. The Jockey name was chosen because it hinted obliquely
at the jockstrap.
It was the high-waisted boxer short that would become the typical underwear choice through the 1940s - it was part of
standard issue attire for the US Army - and 1950s, when male movie stars, if shot in their underwear, almost always
wore this more discreet, more sartorial style. But it was the brief that quickly won a reputation for being
progressive and dynamic; initially briefs were considered so radical - read offensive - by some onlookers that
underwear models had to have their faces blacked out in the photos.
An ad from the early 1940s, for then giant underwear company Munsingwear, acknowledged that the choice was fast
becoming a point of argument among men: a man in briefs - “streamlined, modern, what a getting-around guy needs,” he
says - mocks his boxer short-wearing pal as “old flappy-pants-pappy”. Old Flappy-Pants counters by arguing that his
boxers are far more comfortable. “And what about that stingy little number you got on?” he asks of Mr. Skimpy-Wimpy,
as he doesn’t call him.
This perhaps hinted at the yin-yang of men’s underwear that was to last over the years. It wasn’t a matter of
gimmickry - it was the brief that first embraced novelty prints - “underwear that’s funtawear”, as one ad put it,
with well-placed fig-leaves, suitably phallic rockets, getting-down-to-it rulers - though boxers were not far
behind. Rather it was a question of whether to go boxer, because that was to properly cover up and let it all hang
free beneath, or to go brief, to tidy it up into a neat though rather conspicuous package - the Lindford Lunch-box,
or, following the duo’s jaw-dropping, socks-down-their-pants 1989 ‘Top of the Pops’ performance, one’s Milli
Andy Warhol, a dedicated wearer of briefs - he’d order his in bulk, 30 pairs at a time - knew where the line was. A
friend recommended he wear a rival style that really, as it were, beefed up one’s profile. He tried them once before
complaining that they made him feel too self-aware, something akin to how women must feel in uplift bras he
Even medical authorities weighed in, by turns arguing that boxers were better for your bits - letting the air
circulate, letting the fruits hang as low as nature intended - and then that briefs were better for them - lending
buttressing to those parts that needed them. Neither case is particularly convincing - providing your briefs aren’t
too tight, of the kind favoured by the narcissistic body-builders of the selfie generation. These will lower your
fertility. Avoid synthetic fabrics too. That way lies sweaty gonads.
But, all things considered - and, for so many reasons, sweaty gonads really are worth considering - is there a
conclusion on what sort of underwear you should wear? Ultimately, then as now, it’s an aesthetic choice, and
probably at least in part driven by the dictates of fashion: briefs have the benefit of offering a cleaner line
under closer fitting trousers, but - in this writer’s opinion - look a damn sight worse without the covering of said
trousers. Boxers have it on smartness. You can answer the door in boxers. Do that in briefs and you might expect a
call from the Neighbourhood Watch committee. But then how much of your life do you spend with your underwear
actually visible to anyone who’s interested? Of course, that way lies all sorts of misdemeanours - snagged, piled,
greying, over-branded and miscellaneous Mickey Mouse underwear are suddenly excusable. And they’re really not.
Perhaps all this is why the hybrid that is the fitted boxer brief - trim but tailored, cosseting without the
clamminess - has become the underwear industry’s de facto core offer. That may be because, in utterly unscientific
studies, the ladeez are said to prefer them too. Strange, because in all the movies it’s a pair of classic boxers
they seem to borrow. But then there’s no way they’re putting on your tighty-whities after you’ve worn them.