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With the restaurant Drake One Fifty, Jeff Stober is taking his Drake Hotel brand into a very different environment. But it borrows the hotel’s attention to culture and a bit of its loose, Queen West atmosphere: the retro-style photo booth here resembles one at the hotel, and a mural (at right) by the artist Douglas Coupland is incorporated into the space.Peter Power/The Globe and Mail

It is the end of September, and Jeff Stober does not look worried. The Toronto International Film Festival – that yearly deadline for restaurateurs and hoteliers to launch their new wares – has passed, and he's sitting in a cove at his new restaurant, Drake One Fifty, as it prepares to open two weeks later than planned. Some of his 200 employees amble in to test the restaurant's first lunch service. The retro photo booth, just like the one at the hotel, is being assembled. The marble bistro counter is shining with just the right degree of lustre.

Everything is, or will soon be, just right. And the timing? It opens Oct. 2. "There's always another TIFF," says Mr. Stober, his thin, cardiganed figure in a yoga-perfect posture on the banquette. "When you're opening for 10 or 20 years, there will be many TIFFs." This sounds audacious – but to believe Mr. Stober and his creative staff, it's absolutely sincere. His company has a 10-year lease on the space, a former bank in the Financial District, and it's been expensively fitted out with custom-made cabinetry, furnishings and panelling – some of which is made of plywood. Drake One Fifty shows the scope of Mr. Stober's ambition, for his businesses and for the unusual design sensibility that sets them apart. This is a restaurant, but it is also a brand extension: "Drake without beds," as Mr. Stober puts it. Will it work on Bay Street?

If it does, that plywood will be an important detail. The restaurant's interior is by the London designer Martin Brudnizki, who's worked with the private Soho House clubs, but it draws on a style born in Parkdale.

When the Drake Hotel opened in 2004, it was distinguished by its mashup sensibility, blending the old terrazzo floors and wainscoting of the rundown hotel with contemporary additions. Cabinets and panels made of Douglas fir plywood, designed by Torontonian John Tong, were everywhere: straight from the lumberyard but used in a sophisticated manner, and as Canadian as your Dad's garage workshop.

Here, the plywood stands in counterpoint to much more refined materials, like that Calacatta marble bartop – which is thick and solid and keeps going where you can't see it. "We talk a lot about authenticity," Mr. Stober says. "When you put your hand under a marble bar, and you feel that it stops after one or two inches? I hate that stuff. Build it quality, build it to last, and people will recognize that, and you'll be rewarded for those design choices."

This is one of Mr. Stober's credos, and it has turned this former IT-industry entrepreneur into a hospitality impresario and, he is hoping, a Toronto ambassador of design.

At some point, the Drake style became a brand and the heart of a business. The enterprise includes Drake One Fifty, the hotel, three retail stores, and as of April another hotel, Drake Devonshire, in Prince Edward County, designed by Mr. Tong's office. All carry a blend of materials and products that evoke urban thrift-shop Canadiana with hints of Europe and a big dash of Brooklyn.

After that comes an expansion of the original Drake Hotel that will add about 20 rooms and new event space, and then, Mr. Stober hopes, a hotel-restaurant-cultural venue, taking over an entire building in "a fabulous American city." (Mr. Stober has a second home in Manhattan.)

"Going forward, we are the small Queen West brand that we believe has legs," he says. "We believe Torontonians want to stand behind us and we've got something to offer that is relevant."

And the heart of Drake's offering is design: an eclectic combination of new and old, rough and polished, modernist and (very loosely) historic. While the food and beverage program at the Drake properties is serious, the design sensibility is what sets them apart. Sitting with Mr. Stober at the restaurant are two of his collaborators: Mia Nielsen, the Drake's curator, and Michael Awad, an architect, former academic and artist who works as Mr. Stober's sounding board and detail master.

Mr. Awad quotes from a corporate "style guide," really a manifesto for the Drake's vision: "A playful hybrid of respect for heritage and forward-looking contemporary design." There is a slide show of perhaps 100 photos, mostly culled or taken by Mr. Stober himself. Flipping through the sequence, rapt by the presentation, Mr. Stober and company call out references: a hotel in Berlin, the restaurant at the Standard Hotel in New York, a house by the Chilean architect Sebastian Irarrazaval, who worked on a never-built plan for the Drake Hotel. Some themes emerge: a prominent role for art; lots of wood, in various states and finishes; contrasts of old and new, high and low art.

All this plays out clearly in the restaurant, which Mr. Awad says was almost named "Drake Brasserie and Bar." In keeping with the nouveau-brasserie genre of the moment, it feels vaguely classic, but is in fact absolutely 2013. There are seven different kinds of seating, including wooden Thonet chairs, modernist webbed-leather ones and high stools (elaborately custom-made) that look like sixties car seats, only more comfortable.

The art is an integral part of the room. Surrounding Mr. Stober's seat at the banquette is a mural by Douglas Coupland; over the bar is a text-based piece by distinguished local artist Micah Lexier. There are three more installations around the restaurant; they will change yearly. Ms. Nielsen calls it, accurately, a presentation "of really serious Canadian art in a pop tradition."

And wood is important. The ceilings are clad in cork, a strong move that makes the space feel much more rustic than it would be otherwise. In the middle of the dining room is an installation by local artisans the Brothers Dressler, a tipsy pergola crafted from several species of wood, including some salvaged from Georgian Bay. It is a finely crafted piece that sits right on the (very fashionable) boundary of art and design.

Many other elements speak to the "heritage" trend in the design world. Restaurants and hotels like the Standard Hotel in New York and the Ace Hotels evoke a vague sense of the olden days, providing their young urban clientele with an escape from their tech-filled lives. "People can hide behind these techy toys all day," Mr. Stober says, "but the counterpoint is that they have to feel human after all."

The roots of this approach go back about 15 years. After the sale of Mr. Stober's tech headhunting firm, CNC Global, netted him a fortune, he called the designer Mr. Tong to renovate his Forest Hill house. "He was at a transitional place in his life," says Mr. Tong; the two became friends and Mr. Tong served, as he recalls it, as "a design guide."

"We'd sit down in a bar and he'd say, 'Tell me about this. What am I looking at?'"

Mr. Tong, who lives a few blocks west of the Drake in Parkdale, had an unusual approach. It involved lots of "picking through garbage, hacking furniture, messing around." Mr. Tong, who studied architecture, was pursuing this at a time when midcentury modern wasn't hip yet, and Restoration Hardware didn't exist. "The Edison light bulb was impossible to find at the time," he says.

Mr. Tong first theorized the Drake's model in a document called "Undesign: A design sensibility." Much of it has been adopted and carried on by the Drake's team. The hotel is constantly being renovated, with new details (a group of vintage Canadian modernist light fixtures, say), showing up in the interior.

You can see the Drake's model in play at the restaurant, in its version of the Drake General Store: a giant vintage cabinet near the front door. It is an Argentinean pharmacist's cabinet, bought at Brimfield, the Connecticut antique fair that is a favourite of every New York designer and stylist. The restaurant's front vestibule was designed around it. Among the contents: retro cans of maple syrup and a log-shaped pillow, to provide Canadiana; Mast Brothers chocolate, straight from Williamsburg, Brooklyn; and a few things to shock Bay Street, including cannabis-scented candles and a teddy bear holding a cushion that reads BITCH YOU IS FINE. It's all for sale but also to embody the Drake sensibility.

That sensibility is strong and it is, still, on the edge of contemporary design culture. The Drake approach requires money, time and a lot of labour from designers and tradespeople; the references must be local, the furniture can't come from a catalogue.

Still, The Drake is no longer far ahead of the crowd. Take the Drake One Fifty's steel-framed windows, made in the style of New York loft buildings: They were designed in Switzerland, made in Vancouver, shipped here. "They're honest, real materials," says Mr. Awad. And their likes are now, if you scan design and architecture journals, everywhere. "But let's qualify that," Mr. Stober says a bit sharply. "Where in Toronto are they everywhere?"

Now they are on Bay Street. And they, together with the rest of the Drake experience, will probably fit in well; the city's more adventurous dining culture has reached the downtown core, and One Fifty's brasserie model is familiar and not too challenging to conservative eyes or palates. (If you don't notice the teddy bear, that is.)

The Drake Devonshire, which is a total renovation of a small inn, is the next test. Mr. Tong, and his firm TongTong, are designing the interior to reveal the building's history as a foundry, with an architectural language that alludes to farm buildings. (And has plywood.)

For Mr. Stober, further growth prospects await. He has started to view the Drake as a business with growth potential, and he says that they are "looking seriously at a project in an iconic American city that would allow us to bring the entirety of the Drake manifesto," from retail to music, a hotel and restaurant. They are also, Mr. Awad says, being approached by developers in Canada and in Europe for joint projects. "We are cautious," Mr. Stober says. And no matter what, he adds, "We do not deviate from the brand."