There’s a strange, vicarious quality to watching videos of our youth—they allow us to revisit some of our biggest fashion triumphs and blunders, all without the humiliation of realizing that somehow, you can’t fit into a pair of size-30 parachute pants. It allows us to look back and laugh hard, all without laughing toohard at ourselves. Nostalgia, bruv.
All of which brings us to a staple of our childhoods: Len’s “Steal My Sunshine.” Sure, this isn’t an exercise in rote nostalgia for Len—after all, the band recreated a near carbon copy of the video in 2012 with “It’s My Neighbourhood”—but for us, it brings back the hormone-driven sensitivity, the self-loathing self-obsession, andthe roaring mortification of youth. So, here are 8 style tips we learned from Len’s biggest (only?) hit.
Wear Snug everything
Snug Industries might’ve since gone the way of the Mod Robe, but in its heyday—the late ’90s—the streetwear label was among Toronto’s most beloved. Their iconic ‘S’ adorned everything from powder-blue dresses to polyester faux-basketball jerseys (see: above), but they cut their name on futuristic backpacks and impossibly wide-legged, impossibly pocketed pants—and were a staple of the city’s then-thriving rave culture. Snug’s appearance in “Steal My Sunshine” likely signified that the brand was jumping the shark—its promotion by Len is akin to Low Level Flight endorsing Muttonhead.
Still, even if Snug shuttered in 2005, its legacy still lives on—co-founderGreg Blagoev still makes impossibly ugly (but slimmer-fitting) clothing with Winnipeg-based label Szoldier. Still, we’ll always associate Snug with Toronto’s Queen West strip, where, in our youth, we spent all our time chatting up the Jesus-looking dude in So Hip It Hurts. Speaking of that dude, when we saw him recently, he went on an impossibly offensive tirade about Toronto’s homeless, and we had to be all, “Dude, you need to get the fuck away from me right now because you’re destroying my childhood.”
The carefree accessorize with cotton candy
Chances are, if you’re a Toronto-born immigrant kid, you don’t know shit about cottages. (Heck, I went camping for the first time at like, age 26.) Accordingly, most of what you know about cottage country comes from what your heard from your friend Caleb: It was the land of first kisses in canoes, underage drinking, and, thanks to “Steal My Sunshine,” endless Coney Island-esque boardwalks. And, if you wanted to accessorize proper to emulate a cottage bum, there were few better role models than Moka Only, whose endless cotton candy noshing felt like the very definition of whimsical. We’ve since learned that cottages are less about boardwalks and more about playing flip cup on a dock, but still—we long for the era when a pair of Spy sunglasses, a head full of mini-dreads, and a mouthful of the pink stuff made you a king.
Get the angle of your hat just right
Remember when you worked tirelessly to get the curve on your new Pittsburgh Pirates cap juuuust right? Well, that shit, like your Charlotte Hornets pullover Starter jacket, was somiddle school. The key to your soul—your individuality, precious snowflake that you are—lies in how you position your hat. Worn straight, with the brim over your face? You’re a square. Worn backwards, and you’re telling the world that you’re a lone wolf snowboarder with a heart of gold. Tilted to 45 degrees to the left, and you’re a soulful joker. To the other side, and you’re Tom Delonge circa Angels and Airwaves. We could go on, except for the fact that we’ve just made everything up.
Tinted sunglasses are way cooler than vanilla shades
Somewhere, in the mid-1990s, a soulpatch-toting, flame-shirt wearing, alt-weekly editor was listening to Reverend Horton Heat when it struck him right in the seat of his army surplus cargo pants: “Why don’t we use coloured lenses on sunglasses? That would be fukengrüven.” And so it began.
Seadoos are the sporting man’s accessory of choice
Two decades before people started complaining about fixed-gear bikes—and in an era where bike messengers confusingly rode crusty mountain bikes, complete with plastic-bag wrapped saddles—the hip elite were obsessed with other sporting pursuits. Sure, BMX bikes, wakeboarding, snowboarding, and skateboarding were the pursuits of athletic slackers, but those sports were so…. common. If you reallywanted to impress the Candies-sporting ladies, seadooing was a sport so gentlemanly, it made Monster Energy Drink sipping, Disturbed-listening, ATV-riding badmen look as distinguished as editorial cartoons from the New Yorker.
The essential summer uniform
Every summer, every fashion magazine runs stories about the perfect summer outfit, usually involving linen goods, boat shoes, Keds, and cloth belts. Well, GQ, we’re here to tell you that you’re wrong. So wrong. The perfect summer outfit—whether you’re prowling the boardwalk or jousting, American Gladiator style—was rolled out by Len. Dazzling white ankle socks. Osiris D3s. Billabong board shorts, perfect for both the office or the nightclub (no shorter than shin length—who do you think you are, David Cross?). And, of course, the iconic wardrobe essential: the white tank. Do you need anything else? I think not.
Bucket hats. Just… bucket hats
Patented by Jamiroquai but perfected by the New Radicals, the bucket hat might’ve been the most crucial piece of ’90s headwear: Worn backwards with a scowl, and Samuel L. Jackson made it work. Worn by Red Green, and it was reinvented as a rugged cornerstone of hoser couture. Worn by extras in a Len video, and it has the timeless casual appeal of corporate spoof tee. (Wait, that’s not a Ford logo!)
Perfect your boxer-to-pant ratio
If you couldn’t afford giant, shoe-engulfing Snug phat pants—and trust us, they were expensive—there was a budget solution: Simply get size 40 pants, cinch them tightly with a belt, and wear them precisely at the spot where your ass meets your thigh. That’ll expose the perfect amount of your boxer shorts—and the perfect ratio of underwear-to-pants is 3:4, or 75 per cent pant, 25 per cent boxer. (We’ve invoking the rule of thirds here, duh.)