A History of Boxer Shorts

Flat-lay of assorted men's boxer shorts
Image credit: XYXXBrand on Pixabay

Among the longstanding rivalries in men’s wardrobes (bow ties vs. ties, belts vs. braces), few are as heated as the battle between boxers and briefs. The two have been at it in the ring of public preference for decades, with no definitive winner in sight. Trends shift from one corner to the other and back again, with boxers having just recently won another bout by being deemed a seasonal must, although this time as outerwear rather than undies.

While you might be taken aback seeing someone on the street ostensibly in their skivvies, boxer shorts started life as outerwear. They were — no surprises here — shorts worn by boxers. Everlast, a brand still synonymous with boxing gear of all kinds, were the first to make modern boxing trunks. The company was founded in 1910 by Jacob Golomb, who was just 17 at the time, initially to make swimsuits. Golomb moved on to boxing gear at the behest of renowned fighter Jack Dempsey. This was in 1917; two years later Dempsy became the World Heavyweight Champion and his shorts soon caught on. It’s no wonder why. Golomb’s lighter, elastic-waisted shorts were far more comfortable than the clunky, belted versions worn before. 

Vintage painting of boxer Jack Dempsey
Image credit: Library of Congress / No known copyright restrictions
Jack O'Brien wearing boxing clothes
Image credit: Musée McCord Museum / No known copyright restrictions
Rocky Marciano in a fight pose wearing Everlast boxer shorts
Image credit: Tullio Saba / Public domain
Muhammad Ali and The Beatles in a boxing ring
Image credit: Tullio Saba / Public domain

Broadcloth or knitted boxers became widely popular by the late 1920s and by the ’30s were a fully-fledged craze, with Golomb producing them via famed US underthings manufacturer Fruit of the Loom. The design was introduced to Britain in 1947 by John Hill of Sunspel after a visit to America.

Silky patterned boxers proved particularly popular during the Great Depression. This is likely as much down to their novel comfort (replacing as they did the mostly hot and heavy woollen undergarments that came before) as their ability to inject some habilatory excitement — albeit hidden from public view — into an otherwise drab milieu. 

The Second World War boosted boxers’ popularity worldwide, thanks to American G.I.s stationed across the globe wearing them as part of their military kit. Like the army issue T-shirt, they initially came in white, but soon changed to olive green since it was deemed necessary to camouflage even undergarments for fear of enemy snipers. Ditto their elastic waists were replaced by string ties as rubber was repurposed for more pressing parts of the war effort. 

Man in vintage white military boxer shorts and T-shirt
Image credit: simpleinsomnia / CC BY 2.0

The 1980s and ’90s saw another boxer boom thanks to ad campaigns for a different type of clothing altogether. A series of famous Levi’s commercials featuring such young heartthrobs as Nick Kamen and Brad Pitt in white boxer shorts boosted sales considerably. 

Others who chose to pass on Y-fronts include the likes of President John F. Kennedy and Winston Churchill, the former favouring boxers in blue while the latter preferred pink. Proving equally popular on the streets and in the corridors of power, the garment has been a staple of skating and hip hop fashion since the 1990s, often being paired with pants worn below the waist in a style known as sagging.

Boxers are also a popular choice for blokes in the buff on screen, no doubt for being the more modest and generally flattering choice of undergarment. They’ve been worn on film by the likes of a skipping Christian Bale in American Psycho, a stomping Edward Norton in American History X, a stripping Jason Biggs in American Pie, and Brad Pitt (again) battling it out in Mr. and Mrs. Smith. And if anything could settle the eternal question of boxers vs. briefs, it would be this: They are the choice of none other than menswear maven and ad man supreme, Don Draper.


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