A Brief History of Cycling’s Worst Fashion Crimes
What’s the point of our exceptional local cycle kit manufacturers producing the finest riding apparel in the world, stitching the most incredible jerseys and bibs together in gorgeous seasonal colourways, if we go and ruin it all as soon as we’re off the bike? Because post-ride, we don’t seem to care what the hell we look like.
As a habit, it’s infuriating. It’s mind-boggling. It’s maddening. If it were the 1990s, and tatty gossip magazines still existed, the ‘Circle of Shame’ in every issue would feature some shabbily-dressed cyclist in their cringeworthy *après-*cycle attire.
All cyclists know how hard it is to look sexy on the bike – if it’s even possible at all. You’re dressed in clothing that accentuates your squishy bits, and wearing headgear that makes you look like a tier-three bad guy from a long-forgotten 1970s episode of Star Trek. The fact that we can now cycle in something vaguely verging on glamorous, thanks to the designers and craftspeople in our apparel industry, is borderline miraculous.
So why are we so insistent on making ourselves look like total nanas when we get off the bike? We need to do better!
Mercifully, we managed to climb out of the primordial ooze of poor cycling fashion sense when we finally ditched sleeveless cycling jerseys (whoever thought that was a good look) and anklet socks (though some misguided noobs still dare to ride in these); and sometime in the late 2000s there was a brief, disastrous flirtation with knee-high compression socks (it was so traumatic, I’ve blocked out exactly when it happened). But by and large, we’re currently in our Golden Era of sexy cycling apparel. We look fabulous, and we know it.
But then… examine, if you will, Exhibit A: the coffee-drinking helmet-wearer (from the makers of ‘the dad who thinks bootcut jeans are about to make a comeback’). You’ve just left your bike – which cost you the GDP of a small African country – in the street, just to drink coffee; but you’re so paranoid about someone swiping your helmet that you keep it on while sipping your cortado? Make it make sense.
“As soon as the thigh-crushing bibs came off, on went the quad-killing jeanpant.”
And Exhibit B: Not so long ago, it became all the rage – particularly at mountain-bike stage races – to squeeze into the tightest denim shorts available. Everyone did it: from elite-level weapon to weekend warrior, as soon as the thigh-crushing bibs came off, on went the quad-killing jeanpant. These varied in length, from way-too-short to weirdly-long-so-wouldn’t-actual-jeans-be-better? It was a whole look. And it was awful.
I’m glad to see we’ve moved on from that ridiculous eyesore stage of cycling sartorial inelegance. But sadly, the denim shorts have been replaced, and by something far worse: the socks-and-Birkenstocks combo. Which to my mind is a bit like rubbing your eyes with Deep Heat, instead of an onion – either way, it hurts.
Socks and shoes? Yes, sure. Bare feet? Also yes. Birkenstocks or agreeable knock-offs from your local chain store? Yup. Socks and ’Stocks? Uh, no. Denim shorts, socks and ’Stocks? God no, please. Have some self-respect!
I’m sorry. You can’t dress like a runway-model superstar on the bike, and then walk around the race village or beer tent looking like a background extra from a Netflix reenactment of Woodstock. Remember, looking good has never been about comfort; so let’s not let our standards drop just because we’ve crossed the finish line.
We suffer on the bike. We sweat for Strava and style. So let’s leave the Homeschooling Vegan Mother look to the Homeschooling Vegan Mothers. Pretty please.
Ed’s note: We forgot to ask communications specialist David Moseley whether Crocs are allowed?
Read more of David Moseley’s columns here.
The post A Brief History of Cycling’s Worst Fashion Crimes appeared first on Bicycling.
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About this article
- Length
- 647 words · 3 min read
- Published
- October 7, 2026
- Byline
- DAVID MOSELEY
- Source
- Bicycling