Toronto’s Best Dressed: Jamie Webster

As a creative director, Jamie Webster’s job is to make things look cool—whether it’s a car commercial or a music video for Majid Jordan, the pop duo signed to Drake’s record label. But when it comes to clothes, he likes to keep things simple. “Style should be timeless,” he says. “I don’t pay attention to trends.” Most days, he’ll pair a plain T-shirt with tailored trousers from Phillip Lim or Helmut Lang—though he doesn’t hesitate to experiment when the mood strikes (he’s been known to rock the odd kimono). When he really wants to express himself, he turns to his shoe collection. “I like to go beyond the realm of typical footwear,” he says. That might mean throwing on a pair of white Acne sneakers in rubberized leather, or accessorizing his dress shoes with elasticized metallic bands that wrap over the laces. One thing he never wears? Denim. “It’s too constricting, and it doesn’t fit my aesthetic.”