Every season I have a new obsession, an item of clothing that I will end up buying multiple times and wear daily until I’ve worn them out. Past obsessions have included flared-leg jeans, trucker hats, T-shirts with sassy slogans and, until recently, quirky bow ties. I will proudly wear any of these items again when the timing’s right. If there is one thing about fashion that I love, is that it’s out with the old and in with the new, then in with the old again.

Recently we’ve seen a big 1990s athletic-wear revival. Jock favourites like baseball caps and flashy, fluo sneakers are considered high fashion again, as are sweatshirts. Blending early-’90s hip hop with the Mickey Mouse Club, athletic-inspired sweatshirts are back in a big way. Whether they’re embroidered, logoed or printed, I want them all. (Note: I’ve decided to keep all the sweatshirts I bought, pictured below, for this piece. I need help.)

I am big on clothes being casual, chic and comfortable, and I give bonus points on versatility. The sweatshirt can easily be snazzed up with a pair of skinny chinos and a dress shirt layered underneath, or you can wear it with gym shorts on a trip to the LCBO. It’ll also keep you warm this winter and will last much longer than the nubby, acrylic-blend sweaters you’ll find at the same price. —Diego Armand

<-- Varsity Blues

By Stussy

Available at Urban Outfitters. $72

Classic -->

By Nike

Available at Foot Locker. $65

<-- Typography

Saturdays Surf NYC for Gap

Available at select Gap stores and online at gap.com. $45

*All photos taken by the lovely May Truong