Let’s Talk About Shorts

We need to talk. If you’re planning to stay cool this summer, you need less material covering your lower body. Ladies have skirts or dresses. We men have shorts or kilts. The kilt option sounds intriguing, just not enough to become fashionable to all men. So until that day when we men embrace our inner Scot, here are a few tips and examples about rocking the right pair of shorts for the right occasion.


Traditionalists will rail against wearing shorts to a wedding but it’s an excellent move especially during July and August when the sun scorches. Here’s what you can expect others to say. “Wow, I wish I had the balls to pull that off.” From afar you might also hear: “Damn, that guy in shorts is the smartest guy at this wedding.” Or even this from your date, wife or spouse: “You could never pull that off, but he’s got the legs for it.” The objective is to shine without eclipsing the special couple. For that you can try Steve Alan. Try Topman if what you seek is colourful and slim and hard to squeeze into.

Beer Baseball or Softball League

Every Thursday evening I follow a routine before my softball game. I mutter to myself while trying to locate my jersey, sometimes unearthing it from the bottom of the laundry bin. Then I root around my apartment for the other half of my uniform: a pair of cut-off jean shorts. They were pants until the cuff got caught in my bike chain. With a few snips they became a staple of my uniform for the Xtremely Friendly Softball League in Toronto’s Trinity Bellwoods. And no, I’m not the only one with jeans shorts. For some reason hipsters love do-it-yourself jean shorts. If you don’t have a pair of jeans to spare, you can always grab some jean shorts from Levi’s. Try the 511 Slim Fit Cut-off Shorts.

At the beach or swimming pool

The choice is yours. You can go fancy, classic or opt for something bold. Some advice: Leave the oversized and droopy board shorts at home or ditch them altogether unless you’re a professional wakeboarder. For a patterned or bold look, check out the Nautica Stained Glass Swim Trunk ($40). For something more classic, go for Calvin Klein’s Classic Volley ($23.00). If paying top dollar for swim trunks is where your head is at, there are a number of luxury brands who will separate you from your money. One of those brands is Loro Piana. And for a mere $350, you too can own a pair of Mid-Length, Cotton Chambray Swim Shorts. You’re welcome.


How you wear shorts at the office will depend on where you work. You upper- to middle-management types might be wary of bucking the office’s sartorial norms. But if you can get away with it, try shorts with a more tailored fit. Nothing looks sillier than a grown man with ill-fitting, khaki-coloured cargo shorts. Add a woven leather belt to a pair of Polo Ralph Lauren Classic-fit Flat Front 9’ ($75) chino shorts. Looking for something different? Try the Ben Sherman EC1 Chino Short ($37) or Ben Sherman Seersucker Slim Stretch Shorts ($129). Button up an Oxford shirt, strap on a watch and call it a day. Save your plaid shorts for tee time and dress-down Fridays. Or better yet, reserve it for sick days and lounging around the home.

Pierre Hamilton is a freelance writer from Toronto, where some of his best friends describe him as an acquired taste. He enjoys bourbon and scotch, but craves craft beer, overproof Jamaican rum and great non-fiction. He has a very limited style knowledge but knows what he likes. He also produces a monthly music podcast called Sound Considerations. Follow him, but not too closely, on Twitter.
Photo courtesy of Seniju

This is a test