Toronto has an edgy style all its own thanks to new fashion-forward shops, inventive restaurants, and other hot spots

By Jonathan Durbin
Updated: April 17, 2017
Rob Fiocca

On a recent Saturday evening in downtown Toronto, underground superstar the Weeknd made a rare hometown appearance. The 22-year-old musician (real name: Abel Tesfaye)—known for grinding, clothing-optional hip-hop, R&B, and electronic jams—was DJ-ing a set at one of his local hangouts, a speakeasy-style cocktail lounge called Goodnight. It was too packed to dance, but that didn’t stop people from trying; the multiethnic crush of twenty- and thirtysomethings jostled roughly in time to the beat. From the unmarked alley-side entrance to the retro drinks menu (featuring such concoctions as the Monkey Gland and Satan’s Whiskers), the scene had the hallmarks of the kind of nightlife people like to later claim they’d been a part of—the sort of party that, once the hangover subsides, inspires screenplays and fashion shoots and commemorative coffee-table books. Goodnight was impossibly stylish and photogenic. It felt slightly dangerous, out of control, and loaded with possibility.

It was not the Toronto I remembered.

Safe, clean, bland: until quite recently, these were the adjectives traditionally applied to Canada’s financial and media capital. Toronto was known primarily for its livability, and for its admirably welcoming attitude toward immigrants. Yet despite a steady influx of new cultures, the city lacked verve, vitality, a sense of pride or of real identity. What Toronto was missing in character, it made up for in its rigorous pursuit of sensible liberal values. For cultural cues, Toronto looked to both New York and London, while keeping a disdainful eye on its more effortlessly hip older sibling, Montreal. It exported some of its talent to the United States, but—as is generally true of Canadian artists—those who stayed behind found that their fame stayed behind, too. (The Tragically Hip, indeed.)

Lately, however, Toronto has undergone a remarkable sea change, one that’s redefining the city as stylish, sophisticated, cosmopolitan—cool, even—yet still utterly local. Goodnight is emblematic of this new spirit, as is Matt George, the guy behind the bar, who happens to be the owner. A former snowboarder turned entrepreneur who moved to Toronto from England when he was 21, George is street-smart, business-minded, and totally committed to his adopted hometown. In addition to Goodnight—a favorite haunt of Toronto-based musicians such as Drake and Metric—he owns an upscale-casual men’s clothing store, Nomad, that features a selection of up-and-coming labels (Robert Geller; Gitman Bros. Vintage; S.N.S. Herning) and understated Canadian brands such as the easily wearable (despite the name) Wings & Horns. With footholds in fashion, music, and nightlife, George is undeniably wired into Toronto society and beyond. (At press time, he was one of only five people whom Kanye West followed on Twitter.) And his burgeoning empire—which stretches from Toronto’s increasingly polished, high-rise-filled downtown to the Queen West enclave, full of trendsetting shops, restaurants, and bars—mirrors the evolution of the city itself.

Toronto’s transformation can be traced, in part, through its changing skyline. The uninspiring, 36-year-old CN Tower, the tallest freestanding structure in North America, is no longer the city’s defining landmark. In the past decade, starchitects have been reimagining downtown Toronto: there’s Will Alsop’s Sharp Centre for Design at the Ontario College of Art & Design, a black-and-white domino held aloft by brightly colored struts that resemble pick-up sticks. There’s Daniel Libeskind’s alternately lauded and reviled Michael Lee-Chin Crystal, an addition to the Royal Ontario Museum—all steel, glass, and hard angles that sever the stately lines of an otherwise lovely building. Most successful is Frank Gehry’s expansion of the Art Gallery of Ontario, with its graceful, curvilinear glasswork melded to the exterior of the building. And at the heart of downtown—just west of the Financial District—is the monolithic TIFF Bell Lightbox, the $191 million headquarters of the Toronto International Film Festival, held each September.

Plenty of cities can lay claim to high-profile architecture. Paralleling this, however, is an insatiable boom in residential and hotel development. According to research company Emporis, Toronto has more high-rises under construction than any other city on the continent. The view from the roof of my hotel, the recently opened Thompson, recalls Shanghai or Dubai; I lost count of all the cranes. Among the current builds are the new flagship Four Seasons Hotel, opening this summer and featuring Daniel Boulud’s first restaurant in the city; and the massive Shangri-La Hotel, debuting next month with another New York restaurant import, an outpost of David Chang’s Momofuku chain. Both properties arrive hard on the heels of the Ritz-Carlton and Trump hotels that opened in February 2011 and January 2012, respectively.

The real estate market, meanwhile, has been humming along unabated by the financial crisis, a fact that can be partly attributed to immigration: greater Toronto is growing by 100,000 people each year, with the biggest percentage arriving from urban centers in South Asia and China. (It’s a good town for dumplings.) Indeed, the population is large enough to support two Chinatowns in the city center alone, one downtown and one just east. Still other neighborhoods are dominated by émigrés from Italy, Portugal, Greece, and the Philippines. When I was growing up there in the 1970’s and 80’s, multiculturalism was the ethos of Toronto’s immigration policy—in contrast to the “melting pot” drive for homogeneity embraced in the United States—and remains very much a point of local pride. The range and variety of national heritages here is never more evident than during the FIFA World Cup, when the entire city develops a raging case of fútbol fever.

What makes all this especially exciting for travelers is that while downtown Toronto grows ever denser and more international, the city’s creative classes have established stylish outposts all their own. Look at Queen West (one of the city’s thriving art and design districts, anchored along a three-mile stretch of Queen Street); at the Distillery District (a complex of shops, restaurants, and arts organizations located on the 14-acre grounds of a former whiskey distillery, on Toronto’s east side); and at Little Italy (a charming district of bars and eateries along College Street, to the north). In any of the above, you can’t get too far without running into a table crafted out of a reclaimed barn door. There’s a bountiful supply of Edison-bulb-lit restaurants emphasizing seasonal organic ingredients; stores stocking both international and homegrown designers; galleries, theaters, and music venues; and clubs and lounges you might actually want to spend an evening in. And despite the increasingly urbane and worldly vibe, the city still pays tribute to the big-sky country surrounding it. (Drive north from downtown and you reach real Canadian wilderness in almost no time.) In its way, Toronto feels like a frontier town—one that’s in the midst of a cultural gold rush.

Queen West is the apotheosis of the city’s new energy, a swath of row houses and former factories reminiscent of London’s East End or parts of Brooklyn. This is where you’d want to move if you were young and in a band. “My joke was always that you couldn’t find a roll of toilet paper, and now you can get an ironic Sonic Youth onesie for your baby,” said singer Emily Haines, of Metric and Broken Social Scene, a longtime Queen West resident.

On weekends the neighborhood feels like a playground for street-style photographers—not surprising given the ever expanding collection of fashion boutiques. Besides Matt George’s Nomad, there’s Sydney’s, which carries men’s wear from Dries Van Noten, Jil Sander, and Japanese brand the Viridi-anne; and the local label Klaxon Howl, which, in addition to vintage military gear, sells its own men’s clothing: stiff selvage denim and chinos; flannel scarves; ultra-structured shirts. It’s the chic, woodsy look: wear it the next time you’re hiking to a model casting.

For all the global brands, there’s a distinctly local flavor to Queen West—this isn’t Hipsterville, Anywhere. The neighborhood’s two standout hotels, the Gladstone and the Drake, both feature Canadian artworks; at the former, a different Ontario artist decorated each of the 37 guest rooms, while the Drake employs a full-time curator and rotates its collection throughout the hotel every month. Both properties were 19th-century Trunk Railway lodgings that had fallen on hard times before being renovated. Jeff Stober, who bought the Drake in 2001 and reopened it three years later, sees the hotel as a cultural space for Torontonians. “As the downtown core becomes more dense, you can only do so much entertaining in your personal living spaces,” he said. “What happens by default is that the city becomes your living room. From store owners to restaurateurs, everyone recognizes that this is a really good place to pitch a tent.”

Or to build a brand. Stober also owns three shops—one of them attached to the hotel—called Drake General Store. Their stock capitalizes on a groundswell of hometown pride, running the gamut from genuinely desirable stuff (Hudson’s Bay Company blankets) to Canadiana kitsch—maple syrup, red-cedar incense (which, full disclosure, I bought and love), and a decorative ceramic dish that reads I miss the old Blue Jays, a reference to the 1990’s glory days of Toronto’s baseball team.

This sense of affectionate irreverence is pervasive in the city. My favorite instance: a quote from the late journalist Pierre Berton, emblazoned in a hallway at the Thompson: “A Canadian is someone who knows how to make love in a canoe.” At the splendid Frank’s Kitchen, a small, chef-owned spot in Little Italy, half the menu reads like a caricature of what you’d think Canadians might eat: rare elk loin; rarer venison tartare. Both are fantastic.

Torontonians are effusive in promoting one another. After a tour through his Nomad boutique, George took me to a new boutique hotel in the Entertainment District designed by a friend of his named Del Terrelonge. Called the Templar Hotel—“as in Simon, not the Knights,” Terrelonge qualified—the hotel has 27 smartly decorated suites and lofts, a spa, and a chef’s-table restaurant called Monk Kitchen; deploys a Porsche Panamera as an airport shuttle; and features a lap pool with a transparent floor that’s positioned over the lobby’s lounge area.

When I asked for dinner recommendations, George steered me to Woodlot: bakery by day, restaurant by night, in a warm, inviting, bi-level space with Native Canadian artwork on the walls and a casually stylish waitstaff. Chef-owner David Haman’s style of cooking has been dubbed “urban lumberjack” by the Toronto press; though I was skeptical, his food turned out to be the finest of my trip. The bipartite menu offers both “Regular” and “Without Meat” options: whey-fed pork chop and steak on one side, caramelized Jerusalem artichokes and roast Japanese sweet potato on the other. Almost everything comes out of the restaurant’s wood-burning oven.

There wasn’t anyplace like Woodlot when I lived in Toronto. But the restaurant and its small-scale, artisanal approach seem to represent the future: a well-designed, thoroughly confident experience that respects Toronto’s heritage and simultaneously breaks new ground. There was no sense that the place was a knockoff or that it owed its menu and genial vibe to some other restaurant, in some other city. And thanks to the wood-burning oven, I left smelling like I’d been at a campfire. How Canadian is that?

Jonathan Durbin is a New York City–based writer whose work has appeared in Esquire, Paper, and Interview.


Getting There


Most major airlines fly to Toronto Pearson International Airport (YYZ). Porter Airlines ( flies from select U.S. cities to Toronto Island Airport (YTZ), close to downtown.

Getting Around

Toronto’s bus and subway system is efficient and costs $3 a ride—better than negotiating the city’s traffic.


Drake Hotel 1150 Queen St. W.; $

Four Seasons Hotel 60 Yorkville Ave.; $$$

Gladstone Hotel 1214 Queen St. W.; $

Ritz-Carlton 181 Wellington St. W.; $$$$

Shangri-La Hotel 188 University Ave.;; rates not available at press time.

Templar Hotel 348 Adelaide St. W.; $$$

Thompson 550 Wellington St. W.; $$

Trump International Hotel & Tower 325 Bay St.; $$$$


Café Boulud 60 Yorkville Ave.; $$$

Feasting Room Nose-to-tail pop-up (open through Nov.) from an alum of London’s St. John restaurant. 580A College St.; $$$

Frank’s Kitchen 588 College St.; 416/516-5861. $$$

Goodnight 431 Richmond St. W.;

Keriwa Café Seasonal, indigenous cuisine made by a Canadian Siksika tribe descendant. 1690 Queen St. W.; $$$

Luma Inside the TIFF Bell Lightbox and run by Oliver & Bonacini, the duo behind local hot spots Bannock, Jump, and Canoe. 350 King St. W.; $$$

Monk Kitchen 348 Adelaide St. W.; 416/479-4080. $$$$

Origin Go early for creative cocktails on the patio, and stay for favorites like the Bangkok beef salad with mango. 107-109 King St. E.; $$$

Woodlot 293 Palmerston Ave.; $$$


Art Gallery of Ontario 317 Dundas St. W.;

Distillery District 55 Mill St.;

Royal Ontario Museum 100 Bloor St. W.;

Sharp Centre for Design At Ontario College of Art & Design, 100 McCaul St.;

TIFF Bell Lightbox 350 King St. W.;


Drake General Store Queen 1144 Queen St. W.;

Klaxon Howl 706 Queen St. W.;

Nomad 819 Queen St. W.;

Sydney’s 682 Queen St. W.;


$ Less than $200
$$ $200 to $350
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$ Less than $25
$$ $25 to $75
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$$$$ More than $150

Royal Ontario Museum

The Royal Ontario Museum, located near Queen’s Park and the University of Toronto, attracts over a million people each year. Opened to the public in 1914, the Neo-Romanesque brick façade received a dazzling—if controversial—upgrade in 2007 with the Michael Lee-Chin Crystal wing. Architect Daniel Libeskind's deconstructionist plan for the Crystal (five interlocking prisms supported by steal beams) seems to crash into the original building. The museum's permanent exhibits focus on world cultures and natural history, including a stunning gem collection that inspired Libeskind's design for the Crystal, the Bishop White Gallery of Chinese Temple Art, and the second-level dinosaur galleries.

Art Gallery of Ontario (AGO)

This Frank Gehry updated art museum houses over 80,000 works spanning the first century to present day. A revolving roster of exhibits, from Davie Bowie's music and sartorial sense to Jean-Michel Basquiat make for an always interesting day out. Stop by the museum's lovely restaurant FRANK for drinks or a meal.

Drake Hotel

The west end nabe the Drake (as it's colloquially known), exists in, is called Parkdale. Gentrification has cleaned up the area and the building that used to be a flophouse on a gritty stretch that was for many years, largely forgotten until Jeff Stober stepped in and revitalized the beautiful building. He refashioned the stretch into a funky hub where creatives, dreamers and yes, partiers, gather with gleeful abandon. On the main floor a bar and dining room where smaller, live acts play. Downstairs, a more raucous party atmosphere for musicians and entertainers while upstairs, in the patio lounge, the party continues al fresco. Floral wall paper, train shelving and sock dollies crafted by a local artist decorate the hotel's nineteen rooms that range from 'crash pads' to more spacious digs. But take heed, this is a partying kind of hub, so if you're after deep zzz's and otherworldly quiet, think again.

Thompson, Toronto

The first foreign outpost for the Manhattan hotel brand, Thompson Toronto opened in 2010. Its location in King West Village puts it a short walk from the entertainment, art and design, and financial districts, as well as stellar shopping. Common areas in the 102-room property have a sleek, contempo aesthetic: clean lines, richly grained wood, marble, and hits of neo-Baroque damask. Guest rooms boast floor-to-ceiling windows and heated marble bathroom floors. Dining and bar options include chef Scott Conant’s Scarpetta, a 24-hour “modern diner,” and a rooftop lounge with infinity pool and skyline views of the city.