Street Style: 27 looks at the city on bikes (and other self-propelled vehicles)

Words by Kevin Naulls | Photography by Jenna Marie Wakani

There’s no question that Toronto is a city of cyclists (no matter what Rob Ford has to say about it). Still, thoroughfares without dedicated bike lanes can be dangerous, and many on two wheels use side streets to avoid the perils of cab doors opening or streetcar-track slide-outs. That’s why we took to the parks, bike lanes and side streets of Toronto to check out the style of people on two to four small wheels. These are havens where you can find a mom walking alongside an adorable tot in a summer sundress on her fast, fast, fast Razor scooter, and where a casually dressed family spends the day together riding their bikes. And that’s just the beginning: we saw scores of different takes on self-propelled fashion, from the speedy commuter in a form-fitting T-shirt to the slow-going weekend coaster in a flouncy summer skirt. It seems the free-wheeling life has never been more stylish.

Check out 27 looks at the city on bikes (and more) »

For men, the practical—but scruffy—bike courier aesthetic wasn’t the norm (of course, these folks—including one busy architect/industrial designer—were riding at a much more leisurely pace than your average courier). While some guys felt comfortable having a messenger bag snugly strapped cross-body, others opted for a loose button-up shirt topped by a weekends-at-the-Cape straw hat. Skateboarders and long boarders were more casual yet, opting to go shirtless or wearing skimpy tanks. (Landing tricks is a sweaty activity, so we don’t blame them for trying to keep cool.) Even babies were out in the sunshine, wearing sweet brimmed hats for protection, while the ladies let the sun kiss their bare arms and allowed cute skirts to fly in the wind. The most shocking part was that almost all of the people we saw weren’t dripping in sweat, and we’d like to know how they do that.