Go On and Get Yourself Some Bermuda Shorts – Habilitate

Image credit: Queensland State Archives / Public Domain

Earlier this week I sang the praises of short shorts. It’s a style that I have (for better or worse) favoured throughout my life and one that has come roaring back into men’s fashion over the last few years. However, despite my long-held personal allegiance to the skimpy school of men’s shorts, I will admit to being tempted in recent months for the first time by the longer, fuller, and more traditional shape of Bermuda shorts. Allow me to explain myself.

You know the shorts I’m talking about They’re high-rise, loose-fitting, above-the-knee, and almost invariably khaki-coloured. It’s the style of shorts you would expect to see your grandparents wear on a summer holiday or while brandishing a set of garden shears. Or what you might associate with the scoutmasters and private school boys of the world. Or (perhaps somewhat more auspiciously) with what is inarguably the best photo ever taken of Giorgio Armani. 

I’m personally not especially fussed with the details. I don’t mind about the exact length or shape, nor whether they have pleats or cuffs. Or even whether a pair in question might technically count as gurkha shorts. As a lifelong devotee of the 5-inch inseam, the specifics regarding the trousers in question seem like a pedantic Bermuda triangle I feel safer steering well clear of at this stage. 

Image credit: Annie Spratt on Unsplash

But while my own sense of what constitutes a viable pair of Bermuda shorts is about as loose as the fit of the garment itself, there was a time when these matters were nitpicked down to the inch. According to the strict former dress code of the British Overseas Territory of Bermuda where these eponymous shorts have been worn since the 1930s, a pair of Bermuda shorts must have pleats and terminate precisely 7.5cm (3 inches) above the knee. Moreover, they should be worn with a blazer, regimental tie, knee-length hose, and brown or black tasselled loafers. This was deemed appropriate attire for work and even evening wear, so tell that to your boss the next time someone looks askance at you wearing shorts to the office during a heat wave. 

As to how exactly short trousers became forever associated with the island of Bermuda, one famous account traces the immortal style to a tea shop popular with the region’s Naval types run by a Mr Nathaniel Coxon. In response to his serving staff complaining about the blazers and khaki pants they had to wear as uniforms in the crowded tea shop’s sweltering heat, Cox responded by swiftly snipping their trousers short to just above the knee. A breezy, budget-friendly approach to be sure and one that was appreciated by the keen eye of one tea room regular in the form of Rear-Admiral Mason Berridge. He liked the look enough to adopt it for his officers to wear and even added some knee-length socks to complete the ensemble.

Next the island’s most celebrated export duly made its way to members of the British armed forces stationed in other balmy climates and from here gradually filtered into civilian life. Hikers in Britain in the 1930s were particularly keen on them, but athletic types of all sorts and across various continents proved equally enthusiastic, including the likes of Ernest Hemmingway and Winston Churchill. The latter went as far as declaring that ‘The short-pant is a terrible fashion choice. Unless it is from Bermuda.’

Ernest Hemmingway in Bermuda shorts
Image credit: U.S. National Archives and Records Administration / Public domain

Back on the island in question, they remained an item of national dress until 2007, although it might surprise some fans of the style that apparently shorts in any colour other than khaki were seen as the way to go since that particular hue was reserved exclusively for schoolboys. 

Of course, elsewhere in the world Bermuda shorts have historically been a nearly universal sign of the arrival of summer. And, recently, they have been mounting a rather trendy comeback. 

It makes a lot of sense: There has been a natural move towards looser fits and wider trouser legs in these comfort-focused days of pandemic-era living, and the shorter inseam has ruled for a good few summers now. In this context, a return of some looser, longer, and altogether loucher Bermuda shorts feels like a natural evolutionary step. 

It’s also easy to see the appeal. When weighed against my beloved short shorts, a pair of Bermudas feel less risky, less risqué, and altogether more classy. They seem to demand less attention and feel rather more forgiving. You might, for instance, think your legs need to have a certain look and shape if you’re going to pull off a set of skimpy shorts, whereas the more generous dimensions of a pair of Bermudas draw less attention to one’s nethers altogether. Those same proportions also have the effect of reducing all leg shapes — whether longer or shorter, skinnier or larger — to looking roughly similar. It’s an appealing levelling of the standings, so to speak. 

They have also proven themselves to be surprisingly nimble and adaptive despite their reputations as an older and somewhat conservative style choice. It turns out, these are not your granddaddy’s shorts after all. Bermuda shorts certainly pair well with a more classically inclined wardrobe — traditional workwear, for example, or the kind of workwear-infused prep aesthetic that Liam Jefferies discussed in our chat a few weeks ago — but equally in streetwear and runway fashion, where dressing up summer ensembles with some Bermudas has become its own kind of tried-and-trusted move over the years.

All of this has meant that for the first time in my life I’m considering putting aside my trusty short shorts and trying on some Bermudas instead. Perhaps unavoidably I’ve had the Beach Boys singing ‘Kokomo’ stuck in my head for days as a result:

‘Aruba, Jamaica, ooh, I wanna take ya

Bermuda, Bahama, come on pretty mama’

‘Hmmm’, I think to myself every time I play back this sultry stanza, ‘Don’t mind if I do…’