How to Dress Like The New Yorkville Modern Man

New Yorkville Modern Man at John Ferrigamo

Sci-fi sneakers, harness bags, and skincare serums are the definition of cool for the new stylish, modern man in Yorkville.

The second floor of Prada’s Bloor street boutique is a paradise for a certain kind of man. With its minimalist modern lounge chairs, plush checkerboard rug and green velvet curtains, it’s designed to appeal to a man of sophisticated tastes and modern sensibilities, one who covets colourful sneakers and statement jewelry, and scours the internet for the latest runway looks.

Once a rarity in Canada, where men have lagged behind their European counterparts in embracing bold prints and tailored fits, fashionistas can now be found in abundance strolling the streets of Yorkville. Retailers have responded with enthusiasm, and now offer a huge range of adventurous clothes, accessories and beauty products for the man who wants to broadcast his contemporary good taste.


At Prada, bestsellers include Linea Rossa, a collection of jackets, pants, and vests in shiny technical nylon. While these pieces are designed to stand up to the rigours of America’s Cup yacht racing, they’re much more likely to make a splash on the street. Particularly popular, says the black-clad salesman, is the brand’s range of harness bags, which hold valuables strapped to the chest like a fashionable parachute, and belt bags. “People come in asking for them by their model number, 2VL977,” he says, clearly impressed by his customers’ dedication.

At the nearby Gucci store, the star of the show is a footwear collection, which takes up an entire wall. The classic horse-bit loafer remains, but it is dwarfed by a selection of sandals, slip-ons, and sneakers in a Willy Wonka-like array of colours, shapes, textures, and styles. Among these is the Flashtrek, a chunky-soled sneaker that looks like a cross between a hiking boot and something out of science fiction.


Away from the rich hunting grounds of Bloor Street, a smaller but equally fascinating ecosystem of fashion flourishes on Yorkville Avenue. At Off-White, wunderkind designer Virgil Abloh has decorated the store to look like a forest, complete with fake trees and moss, all the better to show off his oversized sweaters, paint-spattered jeans, and shiny vinyl baseball caps. One street over, DECIEM | The Abnormal Beauty Company specializes in a wide range of skin-care products that are noteworthy for being completely unisex. For the modern fashionable man, having the right skin serum and daily cleanser can be just as important as sporting the latest runway collection.

Inside the Yorkville Village shopping centre, Philip Zappacosta’s menswear boutique, philip, offers still more variety for the style-seeking man. “It’s about respect for tradition with a look towards the future,” says Zappacosta of his shop’s wide range of offerings, from Italian made-to-measure Corneliani suits to high-tech sportswear pieces from Paul & Shark. Zappacosta’s newest addition is Atelier & Repairs, an Italian label that takes well-worn vintage pieces like Levi’s 501s and elevates them with colourful patches and flourishes of decorative embroidery. “It borrows iconic pieces from around the world and turns them into fashionable staples. We really like what it stands for,” says Zappacosta of the brand, which offers its wearers sustainability and stylishness in equal measure.

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John Ferrigamo

Despite the popularity of statement sneakers and nylon jackets among Yorkville’s menswear acolytes, the classic suit is not without its place in this brave new world, according to John Ferrigamo, a bespoke tailor with an atelier on Cumberland Street. “I find men are more daring now when it comes to suits,” he says. Like the neighbourhood’s other retailers, Ferrigamo is happy to cater to the new Yorkville man’s colourful tastes, cutting suits in big stripes and checks, in hues of lavender, plum, and bright blue. “Still,” he adds. “It’s not for everyone. Classic tailoring and styling will always be there.”

Indeed, while the pendulum of men’s fashion has swung to the extreme of late, the navy blue suit, the white shirt, and the polished black oxford wait patiently in the wings for their return to centre stage. After all, if recent decades tell us anything about the clothes we wear, it’s that nothing remains out of vogue forever.

READ MORE: Design Outlook 2020.

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