What do a shoe-obsessed hipster living in Brooklyn and a poverty-stricken child living in, say, rural Ethiopia have in common? Well, chances are they both own a pair of TOMS. For every pair of shoes that TOMS founder Blake Mycoskie sells, he donates another pair to a child in need somewhere in the world. It’s called the “One for One” movement, and as of this year TOMS has given one million pairs of shoes to kids who are susceptible to soil-transmitted foot diseases.

After blazing through Argentina as an Amazing Race contestant in 2002, Mycoskie decided to return to the South American country a few years later. That time around, he was determined to immerse himself in the culture. While there, he met up with some volunteers working on a shoe drive that wasn’t really meeting the needs of kids in terms of numbers and quality.

“So I thought, ”˜You know, this isn’t really a great way to keep kids in shoes that need them for school and everything else,'” says Mycoskie, who recently sat down with the Straight at downtown Vancouver’s Holt Renfrew (which carries TOMS) to talk about his company’s humble beginnings, hipster status, and latest holiday collection. “So I came up with this simple idea, thinking it was going to be just for this one village. But then when I got back to the States, we started selling more and more shoes.”

That may have been the case a year into the project, but for the first few months, Mycoskie had a hard time convincing fashionistas that his original design was cool enough. As Mycoskie recalls, the unisex, rubber-soled canvas slip-ons—based on an Argentine farm shoe—weren’t exactly flying off the shelves.

“I remember being in Nordstrom’s and literally begging women to try them on,” says the bohemian entrepreneur. “So I’ve learned that cool is a very elusive term in fashion. It’s like when people say, ”˜It took me 20 years to be an overnight success’—that’s kind of the way it is with cool.”

Since that first year, though, the little canvas shoe that could has taken over. From SoHo to Los Feliz, people are proudly rocking their TOMS.

“And it’s not just hipster neighbourhoods,” says the Cali-based Mycoskie. “I was in Korea at this restaurant, and literally more than half of the people in there were wearing our shoes. I was just like, ”˜This is in Korea! This is so far from Los Angeles.’”

But where to go from here designwise? After all, when a peasant-farming loafer is your sole inspiration, there isn’t a lot of room for holiday bling, right?

Wrong.

Just in time for the Christmas season, Mycoskie is glamming up some of his ladies styles with the Glitters series ($65), which come in gold, silver, black, and pink.

And new this season for men, there’s the Grey Wool Fleck Bota ($90), a stylin’ mid-top lace-up with cozy faux shearling lining for winter. As well, there’s the waxed-twill Highlands Brown Bota ($90), a rugged choice for men who aren’t down with TOMS’ classic slipperlike style.

And if the charity aspect doesn’t grab you, keep in mind that buying a pair of these shoes puts you in very good company. Why, just last week, the great Quincy Jones rocked his TOMS on The Colbert Report. But it’s not necessarily the celebrity encounters Mycoskie gets a kick out of.

“What’s really weird for me now is I’ll go check into a hotel in like Chicago, and the receptionist will be like, ”˜Oh, I love your shoes—I have two pairs.’ And it’s like, wow! Then I’ll be getting into a cab and the doorman will be like, ”˜Oh, I got a pair of the black ones.’ I mean, it’s nuts. But I never get tired of it.”