Described by Canadian Art’s Richard Rhodes as “elegant and understated,” the AGO revamp by Frank Gehry added curves and swirls to the original space. (Photo: Raina + Wilson; Stylist: Alexis Honce (Plutino Group); Hair & make-up: Anita Cane (Products: TRESemmÉ Hair Care); Gown: Ramona Keveza; Necklace: Maryam Keyhani; Hat: Lilliput;  Suit: Hugo Boss; Sweater: Pink Tartan; Models: Ashley S. and Mark H. (Elite).)

All of moneyed young Toronto is at the ROM Prom Noir fundraiser tonight, partying with MTV queen and king Jessi Cruickshank and Dan Levy while William Thorsell, former Royal Ontario Museum director and CEO, chats in the shadows. “I want to text but it’s impossible,” says an aspiring Ava Gardner, her glove just covering a forearm tattoo. “My stiletto’s caught in the floor grates,” winces her Grace Kellyesque pal, unwittingly joining the critical chorus against Daniel Libeskind’s renovation of the grand museum. “This new generation of socialites has watched a lot of Gossip Girl and The Hills. They know exactly what to do,” says National Post social observer Shinan Govani. “They send me flowers and thank-you notes. They know how to borrow dresses for parties.”

Left: AGO revamp by Frank Gehry; Right: At the ROM, Daniel Libeskind’s controversial Crystal features diagonal slashes that energize the space. (Photo: Raina + Wilson)

It’s not just the youngsters who know how to strut; Toronto has the swagger right now of a place that knows it’s a place to be. Glassy condos and luxury hotels sprout like wheatgrass shoots. The world’s most successful public film festival illuminates the new TIFF Bell Lightbox this month. If the post-Victorian city was once known as Toronto the Good, today’s slightly louche urban playground, home to both a prim new Ritz-Carlton and a phallic Trump tower, is closer to Toronto the Badass. The Wall Street Journal recently winked that it’s a favoured destination of pro athletes, who like its “libertine gentleman’s clubs” and “cool international vibe.”


If any of the above makes you roll your eyes, you’re in good Toronto-bashing company; even the CBC commissioned a 2007 movie called Let’s All Hate Toronto. The Centre of the Universe, Hogtown, the Big Smoke – nicknames that, I assure you (as a native Western Canadian who lived for several years in Quebec), are used frequently and derisively by the rest of the country.

Take another look. Not that Toronto is asking you to. Toronto doesn’t care anymore; it’s done seeking your approval. Its favourite multiculti son, Armenian-Canadian filmmaker Atom Egoyan, cares so little that he set his latest film, Chloe, in Toronto – not Toronto as Chicago or Toronto as New York but Toronto of the tony, money-scented and celebrity-cheffed Hazelton Hotel and the venerable Windsor Arms, where Tiffany bags and flawless facelifts crowd the tea room on this Sunday as I check in. I’m camped out for a few days in my own butler-serviced suite in a hotel so homey, one music-industry guest comes to breakfast in his bathrobe.

The Windsor Arms is a civilized place to be, whether just for tea time or for an extended stay. (Photo: Raina + Wilson; Dress: Marika Brose; Shirt and pants: J. Lindeberg; Shoes: Townshoes.)

Everything Old Toronto is new. A changing of the garde-manger has made Splendido, where a champagne trolley and Bay Street bankers long commanded the tables, a redecorated hot spot again. I graze on a value-priced half-portion of rabbit pappardelle, transfixed by the dark and handsome half of a first date at the next table and the uncork-and-decant ritual being performed for the suits in the corner.


Over a few days, I inhale a tobacco-infused, dry-ice swirled Mad Man cocktail at Barchef; caffeinate on theatrically brewed “siphon coffee” at Sam James Coffee Bar; and chew a tartare sandwich, hot-sauce inscribed with the word “horse,” at the Black Hoof (named one of the best new restaurants in the country by enRoute in 2009). Decadence is clearly in again. Other smart restaurateurs are indulging in a rethought comfort-food groove, like molecular gastronomist Claudio Aprile, who opened the fast and loose east-side Origin, where frozen rocks of malted-milk foam top a spicy chocolate pudding nearly as sexy as the chef himself.

Caplansky’s is the spot to get your hands greasy with delicious, caloric, meaty marvels. (Photo: Raina + Wilson)

“Lean” is a four-letter word in Toronto the Badass. At Caplansky’s Delicatessen, crowds order fatty and extra-fatty smoked meat in such quantity that its namesake owner, Zane, had to invent dishes (like the brisket-stuffed burger) using the slender cuts. His life story is Toronto in a nutshell. As the delis of his youth disappeared, Zane Caplan rode his motorcycle to culinary adventures abroad before returning to open Caplansky’s – he reverted to his family’s original surname – last year. “Feeling good about who I really am is a big part of what I’m doing,” he tells me from behind the bar, simultaneously greeting guests and pulling drafts. “I don’t have to be what the rest of the world wants me to be: I’m fine as I am.”

The past weighs in as I stroll the hipster ’hoods of the west end. If MuchMusic brought first-wave cool to Queen Street West more than 20 years ago, the Drake and Gladstone flophouses-turned-hipster hotels – both have their own art curators – define the wild West Queen West. Boutiques like Fawn (short for fashion, attitude, wit and nostalgia) and sartorial den Green Shag have decor so artfully distressed, merchandise so vintage-quirky, they look like they’ve been there forever. As I heft industrial relics repurposed as decor objets at Commute Home and Ministry of the Interior, I think about what Richard Florida told me about Toronto’s revitalizing waterfront. “It’s a terrific analogy for a city that is transitioning from its industrial past to a post-industrial future,” said the author of The Great Reset and the director of the University of Toronto’s Martin Prosperity Institute. Toronto is embracing its gritty history with a new affection, a nostalgia that trumps even Trump and the other glittering downtown gems that thumb their noses at the – recession? What recession?

A U-shaped gentrification curve is crawling up the restaurant corridor on Ossington, past the queues at Foxley and Pizzeria Libretto, to a formerly forlorn stretch of Dundas Street, where Show & Tell gallerist Simon Cole tells me, “Dundas is the new Queen West.” By the time you read this, nearly a dozen galleries and a handful of new restaurants will be hopping.

But go east, according to Toronto’s black-T-shirted, tattooed philosopher king Mark Kingwell. Perched on his familiar dais at the Park Hyatt’s 18th-floor Roof Lounge, sipping a gin martini, he points to the redevelopment in the area of the blighted Regent Park housing project as a portent of eastward revival. “In the early 1900s, the Bloor Street Viaduct healed these two parts of the city together; it was our version of the Brooklyn Bridge,” says the contributing editor of Harper’s Magazine, evoking the dirt-streaked Toronto of Michael Ondaatje’s In the Skin of a Lion. “Culturally, it needs to happen again – movement between the two sides.”

Kingwell himself is part of a next-gen Toronto legacy, a line of brainiacs ranging from homegrown intellectuals like Innis, McLuhan, Frye and transplanted urbanist Jane Jacobs to contemporary Toronto-derived authors like Naomi Klein and Malcolm Gladwell. In a smart city like this one, it’s telling that what jump-started the current boom was mega-architecture projects behind cultural institutions: Libeskind’s ROM, the Frank Gehry remake of the Art Gallery of Ontario, the Four Seasons Centre for the Performing Arts and the stunning new home of the Royal Conservatory of Music. As he gives me a hard-hat tour of the TIFF Bell Lightbox, Toronto International Film Festival director and CEO Piers Handling notes the transformation: “There’s been a complete rejuvenation of culture in this city in the last few years. I can’t think of too many other places in the world where you see this kind of investment in the arts – maybe Berlin in the 1990s.”

We recommend the bloody caesar at Mark Kingwell’s regular hangout, the Park Hyatt’s Roof Lounge. (Photo: Raina + Wilson)

I feel like I’m crossing an East-West Rubicon of my own the next day when I pull my wheeled suitcase down unfamiliar Queen Street East. I’m headed for the Ivy, a four-room micro-hotel within Verity, a women’s club founded six years ago by former investment banker Mary Aitken as a modern alternative to the old boys’ club. “People may be virtually connected with their laptops and BlackBerries and can work anywhere, but they’re still seeking real-time connection in public spaces,” Aitken says. Places like this create points of contact for Toronto’s thinkers – from the cultural intelligentsia to CEOs and entrepreneurs – to springboard their ideas into the world.

The air is electric with connection in the lobbies and lounges of a handful of new luxury hotel-residences that now define downtown: Thompson, Ritz-Carlton and Le Germain will soon be joined by Shangri-La and Four Seasons. As explained by Dan Menchions, a principal in taste-making firm II BY IV design (responsible for the Trump tower interiors and the Thompson Hotel roof deck), “When I travel to Paris or London or Tokyo, I go to hotel restaurants and bars because they’re destinations in themselves. We haven’t had that before in Toronto. In the next few years, there will be a totally different lifestyle available in this city.”


An elite new shopping enclave downtown is ready for it. I wander the cool white calm of the Room, stroking the racks of cutting-edge Roland Mouret frocks and marvelling that I’m actually in the Queen Street Bay store. In the 1930s, a space called the St. Regis Room at what was then Simpson’s department store brought international fashion to Canada; this year it came back, a symbol of the post-recession renaissance of the city centre. “For years nothing happened downtown,” says creative director Nicholas Mellamphy. “It’s a whole new Toronto.”

At the Thompson Hotel, Toronto firm II BY IV designed the rooftop lounge. (Photo: George Pimentel)

I, too, am on a reinvention quest tonight during a Cocktail Cooking School at Ame, the nearly over-the-top Asian-themed palace of TV restaurateurs the Rubino brothers. A bartender named Moses delivers the gospel about combining sour, bitter and sweet, a flavour progression that reminds me a little of this city’s recent transformation. Choosing from a rainbow of fresh raw fruit, I toss a few lemon and lime wedges in my mixing glass, smoothing their tartness with bright, ripe nectarine slices, strawberries and sweet raspberries. I add just a dash of a Fee Brothers artisanal tincture because being bitter is so 1990s. I mash it all together with some red vermouth and strain it into a chilled martini glass. I take a sip: the perfect balance. All around me, beautiful people nibble gorgeous food from nimbly manoeuvred chopsticks and sip from slender stemware. They sink back into cushy banquettes, talking and laughing long into the night, caught up in the whirl of a metropolis that has relaxed, at last, into being Toronto.

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Where to Stay

The bijou Windsor Arms Hotel has 28 rooms with attentive butler service and sonic-boom sound systems. The lobster-studded mac ’n’ cheese in club Twenty Two and a weekend cuppa in the Tea Room are musts.
18 St. Thomas St., 416-971-9666,

With four rooms, the Ivy is the smallest hotel in the city, but it’s large on luxury with Hästens beds and Bulgari toiletries in each spacious terraced room. Lorenzo Loseto’s soulful cooking at George is your sustenance (think veal sweetbreads, white lasagna, lemon thyme dust); the lomi lomi massage at Sweetgrass Spa, your salvation. Sorry, guys: the ozonated pool in the adjoining private club, Verity, is for women only.
111d Queen St. E., 416-368-6006,

Choose from three new properties this fall: Francophiles will feel at home at Quebec chain Le Germain’s second Toronto hotel; glamour seekers will converge at the Thompson’s rooftop pool lounge; and aficionados of old-school luxury can sleep easy at the Ritz-Carlton.

Hôtel Le Germain Maple Leaf Square 75 Bremner Blvd., 416-649-7575,
Ritz-Carlton, Toronto 181 Wellington St. W., 416-585-2500,
Thompson Toronto 550 Wellington St. W., 416-640-7778,

Where to Eat

Even after the film festival decamps, celebrity spotting is easy for Food Network fans – simply dine at Asian tapas and sushi boîte Ame (brainchild of the Rubino brothers from Made to Order) or at the cozy no-menu, prix-fixe Ruby Watchco (the daily whim of Restaurant Makeover and Pitchin’ In’s Lynn Crawford). To sip and be seen yourself, sit on Origin’s hopping bar side, or at the low bar edging the open kitchen to see the chef dish out manchego risotto topped with chorizo. At Splendido, new co-owners Carlo Catallo and chef Victor Barry have made it the place to dine again with dishes like chilled English pea soup and suckling pig. 

Ame 19 Mercer St., 416-599-7246,
Origin 107 King St. E., 416-603-8009,
Ruby Watchco 730 Queen St. E., 416-465-0100,
Splendido 88 Harbord St., 416-929-7788,

The modern carnivore food chain looks something like this: chef Ben Gundy’s Olliffe, a mecca of picnic-perfect deli meats, including black-walnut-fed wild boar; Caplansky’s, where the smoked meat will save you a trip to Montreal; and Hoof Café and its big sister Black Hoof, home to the most deliciously fashioned animal bits (no wonder enRoute named it one of Canada’s best new restos in 2009).  

Black Hoof 928 Dundas St. W., 416-551-8854

Caplansky’s Delicatessen 356 College St., 416-500-3852,
Hoof Café 923 Dundas St. W., 416-551-8854
Olliffe 1097a Yonge St., 416-928-0296,

In the goth-boudoir atmosphere of Barchef, the staff performs molecular mixology alongside classic bartending for low-key yet sophisticated imbibers. Speaking of low-key, there’s no seating space or Wi-Fi at award-winning barista Sam James’ place, where pilgrims go to take a shot of serious third-wave coffee (anyone for a siphon brew?).

Barchef 472 Queen St. W., 416-868-4800,
Sam James Coffee Bar 297 Harbord St., 416-341-2572,

What to Do

To fill your culture tank, visit the TIFF Bell Lightbox, whose gallery is showing a Tim Burton exhibition from November 18 through April next year, featuring 700 artworks from the filmmaker’s twisted imagination. Enjoy a local-cuisine brunch at Frank restaurant before touring Gehry’s updated Art Gallery of Ontario; then head to the Royal Ontario Museum for a peek at Daniel Libeskind’s renovation. 

Art Gallery of Ontario 317 Dundas St. W., 877-225-4246,
Royal Ontario Museum 100 Queens Park, 416-586-8000,
TIFF Bell Lightbox 330 King St. W., 416-968-FILM,

Remnants from bygone days abound at Commute Home, where you might score a destination banner from one of the city’s streetcars. Meanwhile, in rustic digs on Ossington, Ministry of the Interior has retro-cool and contemporary furniture and accessories. Luxury clothing enclave the Room, within the Bay, revives the spirit of the 1930s designer shop St. Regis Room. Fawn is where sophisticated dressing meets rock ’n’ roll style in a hundred shades of black and grey. 

Commute Home 819 Queen St. W., 416-861-0521,
Fawn 967 Queen St. W., 647-344-4703,
Ministry of the Interior 80 Ossington Ave., 416-533-6684,
The Room Within the Bay Queen Street, 176 Yonge St., 416-861-9111