How Toronto’s flashiest tailor designs his over-the-top bespoke tuxedos

As creative director of The Dirty Inc., one of the city’s newest bespoke suit makers, J.S. Vann (a.k.a “Sox”) designs statement finery for a client list that includes Bay Streeters, Raptors players and chef Cory Vitiello. His sartorial approach is fearless: he’s known to experiment with wild fabrics, flamboyant linings and quirky details. (Case in point: this jersey-fied custom suit jacket.) We tagged along as he and his partner Daria Tcherkachina fitted Rob Guenette, the outspoken president and CEO of Toronto ad agency Taxi, for two over-the-top tuxedos: one in classic black, the other a little more out-there. The process involved four fittings over four months, and a final bill of over $4,000. Here’s what went down.

The team meets to chat about Guenette’s needs. “I attend a lot of black tie events and cocktail shit,” he says, “so I need a tux that breathes, but that’s also modern and makes a statement.”

The team decides that Guenette’s first tux will be in summer kid mohair, which is open, airy and moisture-wicking.

Vann and Tcherkachina plan to amp up the look with a bold vest and lining.

For his second outfit, Guenette decides to give Vann free reign. “When I go to a restaurant I like to let the chef feed me,” he says, “so why not give Sox an open brief? He knows more about tuxes than I do.”

Guenette’s measurements are taken over two fittings and the fabric is hand-cut and sewn into a partially constructed jacket and trousers. Then Guenette tries on the pieces. “I’m a tailor’s worst nightmare,” he says. “I gained ten pounds this summer.”

Guenette wants a slim look, with tapered pants. “But I still want to be able to sit down comfortably,” he says. Other topics of discussion: buttons, ticket pockets and, most importantly, lapel size. “If it’s too exaggerated it looks like the suit is wearing you,” says Guenette. Once the details have been hammered out, the garments are sent to Montreal to be hand-stitched in an artisanal factory.

Three weeks later, it’s time for the big reveal. Guenette’s classic black tux pairs a bold lining with an exaggerated houndstooth vest.

“You know how people say you can tell a guy’s style from his shoes?" says Guenette. “Well I think it’s from their trouser length. Someone can have a well-fitting suit, but if their trousers are too long or bunched up at the bottom, they might as well go home.”

Guenette’s second suit is a sophisticated take on the Canadian tuxedo with cowboy pockets, a thick waistband, wide satin lapels and angled pockets. It took Tcherkachina a while to come up with the concept: “He’s such a fashionista—there’s nothing he doesn’t have,” she says. Guenette’s reaction: “That’s so hot.”

With a few more touch-ups, Tcherkachina’s confident the fit will be spot-on—and Guenette can’t wait for all the compliments he’ll get at his next party.