My brother was coming down to breakfast at his house mid ride when he caught my sister in law’s eye over coffee and she said to him “those are mine.” Not angrily. Not yelling across the room. Just matter of factly. He had picked his off the communal laundry hamper that morning because his own shorts were still wet from being washed and had ridden four miles before she noticed. His reply, paraphrasing only slightly, was “they were the only clean ones and my ass has never been happier.” That was about six years ago and he’s gone out and purchased a pair of “her” shorts since just because they fit well.
I mention this story because I spent twenty years operating on the unconscious assumption that bike gear divided itself into men’s and women’s along similar lines of what showroom floor I worked, athletic underwear excepted, and never considered the question at all. Tops hung on one side of the store, pants on another, women’s was never over here.

That’s how it was when I started working retail in 1988 and that’s how it stayed until I stopped thirty years later. Bike shorts were never an exception in my mind because I didn’t realize that maybe they should be, not until my brother publicly embarrassed me into it.
What “women’s” actually means when we’re talking about shorts and why that might not line up with your brain
First fact that nobody spells out to you when you’re perusing the cycling knickknack aisle because teenage-boy employee specialist has no clue, the differences between a pair of men’s shorts and women’s are actually pretty minimal. Cut through the hip/waist region, and the shape of the chamois pad. That’s it. Other than that they are identical products, often from the same manufacturer down to the fabric, compression, stitching, leg gripper, engineering, you name it. The reason they have two cuts is that female shorts often have a looser cut through the hip relative to the waistband and a differently shaped pad because women load a saddle differently than men do. Real, tested difference in pelvic structure there. It isn’t marketing. Not for that reason.
It also isn’t true for every body type that exists. I should know, my brother has shoulders so skinny and hips so wide that he could only find shorts that fit him properly if he looked in women’s. Only way “they” fit better was because his actual body mapped better to that particular sizing chart, not because he was making a fashion statement. He wasn’t being rebellious. He was being comfortable and goddammit comfort should be the goal at mile thirty on a bike saddle.
I want to talk to the version of me that worked the men’s clothing floor in the 1980’s and would have given my coworker side-eye if he tried on a belt from the women’s department. We thought that gender was what divided these clothes, dressing outside of your “section” meant something about you. Watching my own brother shamelessly don “her” shorts and absorb no social repercussions whatsoever was what it took for that epiphany to click for me. Never once did he say, outside of telling me this story mind you, that anyone gave him crap about his shorts choice. He just bought a new pair because they were bike shorts and they fit.
So… actually does it matter? Is this problem already solved and wearing a controversy jersey
Ok, where Reg goes rogue I generally stay in line so when I say this next bit will be blunt feel free to quote that as fact. No. It doesn’t fucking matter. Not like the question wants you to believe. The question of “can a man wear women’s cycling shorts” is actually “will people care what I wear” and the reality of that answer is that some will. Some will definitely give you sideways looks if part of your package includes hyper-masculinity. My response to those people? Fuck you ride them. The chamois doesn’t care what you throw between your legs, it’s going to pack all up like you were riding on porcelain starting at about ride number two if it isn’t shaped correctly for your sit bones. No one cares what you wear on the bike saddle quite like your sit bones do. That’s the conversation we should be having.
I wear a pair of ~2015 men’s bib shorts for anything over two hours because the padding in those babies is the tits and when some company puts out a new shorts line touting “better sexier ninja comfort technology” I scoff at my local bike shop. I’ve read that line, verbatim, on too many hangtags to believe moisture-wicking bullshit when the pair I bought six years ago continues to outperform everything else I’ve tried since. Comfort.

Fit. Those are things you can’t put a price tag on because you learn what those feel like when you try fifty pairs and finally come back to the ones you walked out on years ago.
I ride what fits. Period. Doesn’t matter if it says “women’s” or “unisex” on the label because no one at the best bathroom on the ride is going to care what you bought, they’re going to notice if you can’t stand up at the end of it. Some of you fit the womens cut. Some of you fit men’s. Some of you fit both. Wear whichever shorts make you comfortable and stop giving a fuck about what they say on the inseam because, believe it or not, we’ve been having this exact argument about fifty other products I sold during my retail career and hopefully learned better than to do thirty years ago.
Reg spent thirty years buying for a menswear shop floor in Sheffield before it closed. He writes about clothes built to last, compares every new buy with something he’s owned for twenty years, and has made most of the expensive mistakes already.



