The Crusade for Cool Shorts

40 pairs of not-so-dorky shorts (including vintage recs)

Jul 18, 2025

∙ Paid

I’m currently on a mission of utmost importance - sourcing shorts that don’t make me look like an absolute dweeb. I’ve been a life long shorts wearer; as someone who runs hotter than a furnace, and grew up in the Florida of Canada, I never had much of a choice. And despite moving hundreds of kilometres north, global warming is beginning to make pant wearing a dangerous task in the midst of summer. So, while we collectively endure this heatwave, I figured I’d task myself with finding some interesting summer shorts that don’t make you feel like a Boy Scout.

I’m sure many of you relate, but I find shorts to be one of the most unflattering items of clothing by default, with 95% of pairs on the market constructed with horrid proportions. The two biggest culprits for poor fits which I see on a daily basis - slim leg openings, and shorts which pull up at the crotch (particularly an issue for those with bigger thighs and asses). I think the inseam wars are actually a bit pointless, 3” and 11” inseams can both look great so long as the fit is appropriate. So, let me put you folks onto some shorts that don’t fall victim to these classic design shortsights. Enjoy!