Even as a development boom dramatically reshapes its skyline and an ambitious creative community positions it on the global stage, the city of Toronto still can’t quite get used to the idea that it’s kind of a big deal.

Credit: Michael Graydon

If you're ever in Toronto, a friend had told me, make sure to search out Jen Agg. Agg co-owns the Black Hoof, a farm-to-table, nose-to-tail restaurant on Dundas Street West that, many agree, has transformed Toronto’s dining scene since it opened, seven years ago. In her thirties, Agg has long brown hair and an almost predatory conversational style. “Are you mansplaining feminism to me?” she asked as we shared an asparagus dish with whipped burrata and mullet bottarga—fish roe cured to the hardness of Parmesan, then grated. “Is that what you’re doing?” I liked her immediately.

Since Agg and her husband, the Haitian-born painter Roland Jean, opened “the Hoof,” as she calls it, they have added Rhum Corner, a Haitian-style rum bar next door, and Cocktail Bar, a jewel box of a place across the street. Agg refers to the three together as “Hoofland.” On a Friday night, Hoofland was hiving with youngsters. After the rush, Agg and I settled down over Manhattans at Cocktail to discuss how she and Jean had built their mini-empire. The skyline from Sugar Beach Nikole Herriott

“The design of the Hoof is almost an anti-design,” she told me. “I’m sure you noticed the Edison bulbs and barn boards.”

I assured her that I had.

“Nicely done. Because it has neither of those things. Everyone thinks it does, but it doesn’t.” What it does have are Eames barstools, Marais chairs in seafoam green, and nothing on the walls aside from plain dark wallpaper and three angled mirrors. Rhum Corner was conceived as an idealized version of Jean’s birthplace and a tribute to the couple’s marriage, with lights strung across the ceiling, Baron Samedi art, and a voluptuous mural by Jean of a young woman, naked except for an olive-green army cap, glancing over her shoulder, Ingres-style. “You’re supposed to feel as if you’re on an outdoor patio in the Caribbean,” Agg said. Oysters and a Duro Ocho, a rum-based drink, at Cocktail Michael Graydon

And Cocktail Bar? “This is the most beautiful room I’ve designed.” I could only agree. A free-standing fireplace greets you upon entering. There are old leaded-glass windows in the cabinet doors of the back bar. The walls, barstools, and banquettes are charcoal gray. The tin ceiling reflects the room’s candlelight. The joint is dark; the joint glows. A perfect cocktail feng shui having been achieved, Agg and I traded progressively more incoherent barbs into the late hours.

She told me that she feels Toronto has “tall-poppied” her—punished her doubly for being both immodest and a woman. Blunt and ambitious— especially blunt about being ambitious—Agg expressed her frustrations with Toronto pungently. “The world will pay attention to you before this provincial town will,” she said. And the world has: Anthony Bourdain named the Black Hoof his favorite restaurant in Toronto, and Agg and Jean have teamed up with members of the band Arcade Fire to open a Haitian restaurant, called Agrikol, in Montreal later this year.

Agg was, from all appearances, trying to kill off her inner Canadian, even as I was trying to cultivate mine. Shame on me. I had arrived in Toronto expecting that famous Canadian modesty from everyone I met.

Before I spent time in Toronto, I had lazily classed it in my mind with Seattle and Portland—laid-back metropolises populated by well-adjusted knowledge workers. And it’s true that Toronto is nothing if not well-adjusted. Cops here are more likely to have bikes than weapons; cars slow down for a yellow rather than gunning it; passersby say “excuse me,” often for no discernible reason.

But Toronto is also the biggest city in the country. It is not to Canada as Seattle or Portland is to the U.S. “You could drop a small nuke in Trinity Bellwoods Park, and the entire cultural class of Canada would be wiped out,” Stephen Fowler quipped. Fowler, a preternaturally young-looking 51-year-old, moved from San Francisco to Toronto with his Canadian wife a dozen years ago, then watched in despair as everything that he is—a twirlymustache- sporting, vintagestore- rummaging, vinyllistening kind of guy—became a hipster cliché. He runs the Monkey’s Paw, an antiquarian bookstore in Little Portugal that is filled with lost curios and oddments of the Englishspeaking world. Spread across the tables of his little storefront on Dundas Street West are titles like Werewolves in Western Culture and A Guide to Gravestones and Gravestone Rubbing. Fowler is one of the more acute observers of civic manners I’ve met. He sees Toronto’s dilemma this way: From the Canadian perspective, it is the striver city the rest of the country resents. But from a global perspective, it remains a provincial city where the brightest lights leave for London or Dubai. “Or worse,” he adds, “for New York. Beneath all the decency and modesty is a chip on the shoulder so huge it took me years to understand it.” Candy Apple, a street performance group, in front of a new condo in Little Portugal Michael Graydon

Toronto’s divided self has always found expression in its urban design. In a sense, there are two Torontos: the highly planned, highly developed city known as “downtown,” a word locals sometimes say with an air of exasperation, and the city of “the neighborhoods,” enclaves of civic spontaneity like Little Portugal, where Hoofland is located. The seminal urban theorist Jane Jacobs commented on just this aspect of the city when she moved here in 1968 from her beloved Greenwich Village. “Toronto is a very refreshing city to come to from the States,” Jacobs said on a Canadian TV program. “It’s all full of romanticism and quirks and surprises and ingenuity, particularly in the way outdoor space is used.” But Jacobs also recognized Toronto’s “civic schizophrenia,” as she put it. On the one hand, it was a bottom-up, fun, free-spirited city of creatively repurposed public spaces. On the other, it was a top-down, pompous, overplanned city that seemed perversely devoted to stamping out its more creative twin. Mjölk, a design store in the Junction Michael Graydon

As of 2015, the situation has grown more curious. For most of the past decade, Toronto has been a skyline of cranes, each hoisting a fresh glass-skinned tower up from a podium slab. The boom is partly thanks to Canada’s strict lending standards, which allowed it to largely avert the global real estate bubble. And so, ironically, it was the country’s infamous prudence that helped unleash the current wave of construction and speculation. Developers completed more than 20,000 new condo units across the greater Toronto area last year, an all-time record. And yet, though international money pours in, it is not the case that pompous Toronto is swallowing indieartsy- Etsy Toronto whole. The two now encroach upon one another in novel and disorienting ways. For downtown, that means borrowing from the cachet of the arts scene, sometimes to sell real estate that is unremarkable. For the art and culture scene, it means courting international recognition and money. The key term for both is design.

“Design has followed food as the lure,” said John Baker, who co-owns Mjölk, a hybrid art gallery–design boutique in the Junction neighborhood, northwest on Dundas Street West. With his chunky Yellows Plus eyeglasses and Viridi-Anne high-waters, he could be a “creative class” avatar in Sim City. Down to the last item, his store, which reflects Japanese and Scandinavian influences, is exquisitely curated. He seeks recognition abroad, he told me, as a means of getting Canadians to acknowledge him. “Famous designers design for us,” he said, pointing to furniture by the Italian Luca Nichetto and the Norwegian duo Anderssen & Voll. “Only then do people here talk and notice.”

“Design has followed food as the lure,” said John Baker, who co-owns Mjölk, a hybrid art gallery–design boutique in the Junction neighborhood, northwest on Dundas Street West. With his chunky Yellows Plus eyeglasses and Viridi- Anne high-waters, he could be a “creative class” avatar in Sim City. Down to the last item, his store, which reflects Japanese and Scandinavian influences, is exquisitely curated. He seeks recognition abroad, he told me, as a means of getting Canadians to acknowledge him. “Famous designers design for us,” he said, pointing to furniture by the Italian Luca Nichetto and the Norwegian duo Anderssen & Voll. “Only then do people here talk and notice.” Graffiti in front of a condo development in Liberty Village Michael Graydon

Jonathan Sabine of MSDS Studio, a small firm that has exhibited work at Mjölk and has designed products for the Toronto-based housewares company Umbra, has similar feelings. “It helps to be accepted by the rest of the world in order to elevate our position here,” he said. He and his partner, Jessica Nakanishi, worry that some developers throwing up towers downtown don’t share their values, which they describe as humanism, multiculturalism, and craft. Sabine recalled a developer who bulldozed a building housing artists’ studios and in its place erected a condo called… “Art Condo.” In an effort to shape the Toronto they want to live in, MSDS is working with what Nakanishi called a “thoughtful developer” on a more human-scale condo project. “We want to build things that last,” she said, “that are beautiful rather than glitzy.” MSDS designers Jessica Nakanishi and Jonathan Sabine in their studio Michael Graydon

After chatting with Sabine and Nakanishi, I headed out on Dundas Street West, first on a streetcar near the burgeoning gallery neighborhood of Bloordale Village, then on foot. I passed a squat social-services building the color of whole-wheat pasta and an old Nestlé factory with large bay doors labeled KIT KAT and BATTER MAKING before finding Shane Krepakevich in his nearby studio. Krepakevich began his professional life as a geologist, then became a sculptor, and only later drifted into design. The lighting and furniture he creates under the name the Mercury Bureau is astonishing— seemingly pure investigations of surface, line, and form that are also fully functional objects. He described the things he makes as “large, solid, spectacular,” then wondered whether it were “possible to make something equally strong that doesn’t need to be spectacular to achieve strength.” It can sometimes be difficult to tell whether Krepakevich is speaking literally or in metaphors. Was he referring to design, the life cycle of cities, or time itself? A used book vending machine at the antiquarian bookstore the Monkey’s Paw Michael Graydon

Later, I met Alex Josephson, the beamingly confident cofounder of Partisans Projects, one of Toronto’s up-and-coming architecture shops, who wore leather pants and sported a sculpted hairdo. We were at one of Partisans’ latest commissions, Bar Raval, a swanky tapas joint inspired by the pintxos bars of Spain’s Basque region. He pointed out the “lingerie of steel and Spanish tiles” that hung in the front window and the molten quality of the mahogany structures suspended from the walls and ceiling. The shapes float in undulating patterns that make one think less of the artisan’s touch than of pure computing power. “The back-end nerd factor of all this is insane,” Josephson told me. “Nineteen different software patches. To carve wood!”

Canada’s conundrum, he explained, is that it has money and talent to burn but has historically lacked the egos necessary to bring the two together. The country’s “culture of humility” has translated into very few acts of public extravagance. In the United States, private developers hire starchitects to build legacy buildings. In Canada, the ambition to be “worldclass,” he says, is squandered on “architecture’s version of Fordism. It’s the purest form of prefab, in which the developer repeats the same floor plan, the same suppliers, the same materials, to get economies of scale.”

Josephson wants to rescue Toronto from the dullness of the podiumtower form—to do to it what Bar Raval has done to the pintxos concept, and what, for that matter, his stylist has done to his hair: turn it into sculpture. He imagines a condo structure that rolls like “sensuous hills,” its curvaceous landscape concealing “dynamic interior architecture” and “spatially rich outdoor spaces”—a “Swiss Cheese” tower, “inspired by the spatial richness of the Swiss-cheese block.” Josephson told me that he has already moved beyond the design phase. “I’ve been working,” he confided, “with a developer who cares about the neighborhood.” Jen Agg and Roland Jean at Cocktail Bar Michael Graydon

One raint night, I went to Trampoline Hall, a storytelling event in which people deliver lectures on subjects they know nothing about. Here was the Toronto I’d heard about: youthful, a little boozy, loose, ritualistic, and very fun, not least for not being a self-conscious “thing.” The whole evening shimmered with the delicate feeling of flying just under the radar. Robin Goodfellow, the co-owner of Bar Raval, amid the restaurant’s mahogany forms Michael Graydon

Later, I went for beers with Carl Wilson, one of the event’s founders and a music critic for Slate. “Trampoline Hall came out of a period when it seemed like Toronto was creating a really distinctive arts and culture identity,” he told me, referring to the indie music scene of the late nineties and early aughts that gave rise to bands like Broken Social Scene and Feist. Where that milieu was once spontaneous, now it is more—well, designed. As an example, he motioned to our surroundings. The bar was called Wallflower. I liked Wallflower. It was dimly lit, with floral wallpaper and Christmas lights and votive candles and an old-timey chandelier. It was calculated- eccentric, vintage right out of the box. “It used to be that the places that became bohemian hangouts were actual dive bars, taken over by artists and their friends,” Wilson said. “Now they’re custom-designed for that purpose. It cuts out the middle stage of gentrification.”

On my last day in Toronto I strolled down Dundas Street West with Fowler, who echoed this sentiment. Gesturing down Ossington Street, now busy with latte options, he said, “When I moved here, this was all Portuguese-run kitchen-supply stores and vacant lots. You had your Portuguese doctors, grocers, tax preparers.... English didn’t need to be spoken for days.” In the alleys, men would throw open their garage doors and spend the day roasting sardines, making wine, and playing cards.

Cities are always trying to recover their naïveté, the imagined pointzero before—fill in the blank—gentrification, overdevelopment, hipsterism. To be urban, though, isn’t to be naïve. It is to complain. It is, as Robert Frost said of trees, to talk of going, but never get away. Or as Fowler put it, “Why am I not doing my store in L.A.? People would get it there.” He paused, then added, “Toronto’s just too nice to leave.” The neighborhood vibe of Queen Street West Michael Graydon