Toronto’s Best Dressed: Michael Wekerle

For a notorious eccentric, Michael Wekerle’s approach to fashion is downright conservative. “My mother always taught me to be a well-heeled man,” he says. “Because it doesn’t take any money to make sure that your shoes are polished, that you’re well manicured. The people who look successful tend to be successful.” By that logic, Wekerle is thriving. Whether he’s marching down Bay Street or spewing fire on Dragons’ Den, he favours snugly fitting three-piece suits and starched shirts with French cuffs and big collars, all made in the best, most comfortable fabrics—because, well, he’s earned it. “I make very quick decisions about clothes, and I rarely try things on,” he says. “I know what I like when I see it.” What he likes is big bow ties, rakish hats and sunglasses all day and night—a little business, a little rock ’n’ roll and a whole lot of swagger.