Toronto’s Best Dressed 2014: our annual list of the city’s most stylish people

Twenty-three Torontonians, from shopkeepers to enterpeneurs to heiresses, who paint a portrait of a supremely stylish city

Profiles by Jean Grant, Danielle Groen, Gabrielle Johnson and Michelle Taylor

Chloe rogers is unlike any other Toronto teenager. The 17-year-old daughter of media scion Ed Rogers and his socialite wife, Suzanne, lives in a mini-château in Forest Hill. She spends her vacations in Barcelona, London and Anguilla. And she attends fashion week galas and charity balls with style stars like Zac Posen and Coco Rocha. Rogers recently took her sartorial passion one step further, signing a contract with Elite Models—she’s since appeared in editorial shoots for Flare and The Kit, and donned feathered frocks in David Dixon’s fall 2014 runway show. Off the catwalk, she prefers to dress like any 17-year-old: body-con cocktail dresses, crop tops and skinny jeans. They’re not exactly the pastel confections favoured by her mother, but Chloe insists “she has never raised an eyebrow at anything I have worn.” Maybe Suzanne is just relieved that her daughter only raids her closet for the loungewear. “She has the softest bathrobes ever,” Chloe says.

Suzanne Cohon is a consummate multi-tasker. She spent the last decade building her PR firm into a communications powerhouse, she has an eight-year-old daughter with her ­husband, CFL commissioner Mark Cohon, and she’s also an active philanthropist (she sits on the committee for the Ronald McDonald House’s annual gala). For her chaotic day-to-day, she sticks to a simple and ­stylish uniform: jeans, blazer and diamond studs, amped up with leopard-print Gucci slingbacks, hot pink Brian Atwood pumps or another choice from her 100-pair-strong shoe collection. But at fashion parties and charity dos, she trades out her ­working-mom attire for ­jumpsuits, bright colours and chunky jewellery that ensure she gets noticed.

The 40-year-old owns ASC Public Relations, which reps fashion heavyweights like Calvin Klein, Ann Taylor and Hugo Boss.

“My clients! We work with some of the most creative and talented designers in the world.”

Less than two years into a social work degree at Ryerson, Paul Mason was signed to the Judy Welch agency. In the 26 years since, he’s walked every major runway in the world, and appeared in ad campaigns for Gap and Donna Karan. But despite his industry cred, Mason is wary of looking overly fussy or styled. “I’m not very trendy,” he insists. So what of that hipster beard? His decision to stop shaving was a symbolic act following the death of his mother, but the net result has boosted his modelling career. Mason credits his facial hair with landing his most interesting gigs yet: “Instead of catalogues, I’m booking crazy editorials,” he says. “For a recent magazine shoot, I spent four hours getting fake tattoos all over my body. I never would have done that before.”

Mason has appeared in ad campaigns for D&G and Hugo Boss, and in editorials for GQ and Fashion.

“Daniel Craig, Jude Law—the Brits are right on point with style without trying too hard.”

When Justin Bieber began swaggering around in pants with a crotch as slack as the nation’s collective jaw, it became near-impossible to rummage up a drop-crotch-pants enthusiast. But whether promoting her recent memoir, Listen to the Squawking Chicken, or appearing on her daytime talk show, The Social, Elaine Lui will not ditch the drop. (“The fit is flattering when it’s put on properly, not halfway down the ass,” she insists.) Lui favours ­tailored clothes with strong, structured shapes—boxy tops, ’80s shoulders, a cropped white-pleather jacket she’s worn to threads—that allow her to move from the small screen to the red carpet to the dozen daily posts she writes for her website, LaineyGossip. The one exception to this wearable rule: Lui’s weakness for beautiful, often utterly impractical shoes. Even the most astute sartorial pragmatist needs a vice of her own.

Lui, 40, runs the blog LaineyGossip and co-hosts The Social on CTV.

“Charlotte Gainsbourg, Gwen Stefani and Kate Moss know exactly what their style brands are. That self-awareness sets them apart.”

When J.S. Vann was growing up, the eldest of five kids born to Cambodian refugees, there was always a sewing machine in the house. “My dad would tailor things for us and make sure we looked really good heading to class,” says Vann. “Even though we didn’t speak English, we could still present the right image.” Now, as the creative director for suit maker Garrison Bespoke, Vann helps others do the same thing, whether for Drake (a jacket lined with a vintage Raptors jersey), the Toronto FC (matching pinstripe three-pieces) or his siblings (“I make sure they’re the best dressed for proms and church”). As for his own outfits, it might be polka-dot shoes, quilted pants and a houndstooth jacket one day, head-to-toe orange the next. “People talk about having eclectic style,” he says, “but I really try to live it.”

The 34-year-old Vann is the creative director for Garrison Bespoke tailor shop.

“Kanye West and Tom Ford. I like that they don’t put limits on their creativity. They understand male dynamics and shapes.”

For Jason Burke, sneakers are a lingua franca: they connect him with punk, skate and hip-hop subcultures. Since receiving his first Air Jordans at the age of 12, Burke has owned close to 5,000 pairs of shoes. A good chunk of that collection—snatched up in places like Shanghai, Milan and Copenhagen—is available on Burke’s e-commerce site, Snkrbox, for those with a fondness for vintage kicks and a size-12 foot. (Burke would put any of his shoes on the site, though he does admit to bouts of seller’s remorse.) “I don’t go places if I can’t wear sneakers,” he says. “The Thompson Hotel adopted a sneaker policy because of me.” Find him there in suits with white Chuck Taylors, or skinny jeans with an old-school ­basketball tongue sticking out—unless he just sold those ­Jordan 11 Concords, in which case, find him there mourning the loss over a drink.

Burke, 39, is a retired CFL player who heads up merchandising for Canada Goose and runs Snkrbox.com.

“Kanye West for his attitude. Michael Jordan for his performance. Spike Lee for his cultural influence.”

Lisa Corbo, who grew up in Italy and ­Australia, learned to dress with intention from a young age. “You don’t dress for work or to impress someone—you dress for yourself. Always.” For Corbo, that means making an effort, yet feeling effortless—the key to great style. A good haircut, attractive shoes, a bright lipstick and a smart skin care regime are her foundation. “It all starts from within, doesn’t it? The frock is probably the last thing on my list.” Whether she’s helping clients at her Yorkville boutique, relaxing at home or hosting a fundraiser for the Princess Margaret ­Cancer Foundation, Corbo looks ­striking. Structured clothing in luxurious fabrics, statement accessories and her perfect red lips complete the picture.

Corbo, 53, is the co-owner of Yorkville’s George C. boutique

“My mother, who collected Dior accessories, and my daughter’s way with relaxed separates.”

There’s hardly a job Markus Anderson hasn’t held in his 11 years with Soho House: he walked in a waiter, managed the restaurant, then the club and now serves as a ­company consultant. But it was his time spent as the House’s global membership director that shaped Anderson’s style. In London, where he befriended fashion designers like ­Alexander McQueen, Anderson came to appreciate quality structured jackets and a Chelsea boot. (“They make sense—the weather’s shit most of the time,” he says.) In Sydney, where “it’s crazy hot,” he sought out jeans and T-shirts with a tailored fit. Those pieces now serve as something of a uniform for Anderson, with the occasional cardigan thrown in. “I do enjoy a bit of knitwear,” he says—lucky for him, since Toronto winters are plenty long.

Anderson, 37, is a consultant with the Soho House group.

“The easy style of Paul Newman and Steve McQueen.”

Morad Reid Affifi is a sartorial ­contradiction. He rhapsodizes about the days when men wore their dapper finest to a hockey game at Maple Leaf Gardens, but can’t quite abandon his childhood infatuation with disco colours and fits. He donned a tux every Friday night for a month—he felt good in it, and his tux needed some wear—yet unapologetically advocates for rubber Havaianas flip-flops. It’s created some confusion in his social circle: “My corporate friends think I’m a hipster, and my hipster friends think I’m corporate,” Affifi says. For now, he’s happy to play the double agent.

Affifi, 35, is a partner at the marketing agency Portland Stewart.

“My dad was a huge influence—he embodied classic style. I still wear the vintage Pierre Cardin belt I stole from him.”

Before launching her career as a makeup artist, Misty Fox studied film in Australia and spent a year in London working as a model. “I hung out with plaid shirt-wearing, rarely-showered film guys while getting to wear very beautiful outfits and dresses for shoots,” she says. “This contrast opened up a world of fashion that somehow agreed to meet me in the middle.” While living in the U.K., she developed a talent for vintage shopping, ­scouring Spitalfields and Portobello Road for unique finds. Today, her daughter mixes thrift-store pieces into her wardrobe with ease. “Violet is so free with her expression when dressing; she doesn’t think once about what anyone will think,” says Fox. “She’s an inspiration to me.”

Misty is a 32-year-old hair, makeup and special effects artist. Her daughter, Violet, is seven.

“My style is ’60s- and ’70s-inspired boho with a flash of tattered glamour,” says Misty. “Cool and punky,” says Violet.

Ray Civello feels a little cheated by men’s clothing options. “Guys have so few chances to wear anything fun,” he says. Still, he’s managed some memorable ensembles over the years. In the ’90s, as a young hairdresser at the Rainbow Room, the city’s hottest salon, he favoured all black layers by Yohji ­Yamamoto. These days, he takes meetings, designs salons and reviews financials while wearing slick suits in unexpected hues like steel blue and aubergine, or bold checks. (He opts for even brighter colours on the golf course.) And, as you might expect from a man who takes sartorial chances, he has a dazzling collection of accessories: hats, coloured lace-ups, patterned scarves and, of course, nearly a dozen pairs of his signature thick-rimmed, tinted glasses.

The 56-year-old’s hair empire now comprises 11 salons, five training schools and more than a dozen Aveda stores.

“Though I’m Italian, I love Japanese designers like Comme des Garçons and Yohji Yamamoto.”

When Elissa Mielke meets with music ­producers, she knows she’s one among scores of aspiring singer-songwriters. So she intentionally dresses in outfits that are bold or silly to stand out. Luckily, she has a closet full of memorable pieces from vintage and consignment stores to draw from, like furry leopard-print boots (“They match nothing, so in my mind they go with everything”), a hot pink men’s dress jacket (“I feel like I’m not allowed to be sad when I’m wearing it”) or one of her 30 vintage hats. She finds quirky pieces in stores like Queen West’s Mama Loves You ­Vintage—when she comes in, the staff already know what she’ll try on—and Value ­Villages in small towns, “where people no ­longer have need for their sparkly pantsuits.” It takes serious panache to put together a ­stylish outfit from castaway clothing, and ­Mielke’s got it.

Singer-songwriter Mielke, 24, models for local label Horses Atelier.

“I love the women in the Advanced Style documentary. And Florence Welch from Florence and the Machine.”

A career in fashion sort of snuck up on Lance Chung. He applied for an internship at Sharp magazine while working on a commerce degree at the University of Alberta—and the experience stuck. He later signed on as the publication’s online editor and social media manager, where he drew on his business training to assess the viability of new labels. “In fashion today, there’s so much emphasis on branding,” he says. “A successful designer knows who they are targeting. They’ve done their research. It’s not enough to focus on the ­creative—they have to look at it as a business.” That business-first attitude extends to his wardrobe. He favours basics like crisp white shirts and dark jeans, then adds layers like printed ties and quirky lapel pins. “I stick to a foundation of traditional menswear but play around with accessories”—a clear vision that gives Chung his sartorial edge.

Chung, 25, is a brand consultant specializing in men’s fashion.

“I admire Nick Wooster for his menswear and Lapo Elkann for using statement pieces in a way that’s not tacky.”

Family is a big deal for Sacha Grierson. Not only does she share a business with her mother—Eat My Words, a bakery dedicated to raising money for the Stephen Lewis Foundation—but she describes her own daughter as her “constant companion in everything.” She’s passed her love of everything stylish to Lola, who started taking an interest in clothes at the age of four. “We were going out and she was adamant about putting together her own ensemble,” says ­Grierson. “She did a solid version of ’90s grunge without even knowing it: high-top ­Converse, Roots sweatpants, a tutu, a plaid shirt and a fur hat. It looked fantastic.”

Sacha, 40, co-founded the bakery Eat My Words. Her daughter, Lola, is nine.

“Lola and I travel together a lot. Our style is influenced by our destination.”

After 12 years working in bay street’s finance shops, Michael Burns made the jump to a tech startup in January. Along with the new job came a more relaxed wardrobe: the slim, European-cut suits and silk ties that he once wore to client meetings gave way to jeans and sport jackets—and, once in a while, a pair of cowboy boots. But he still projects the sophistication of a leading man, even in laid-back attire (the silver-grey at his temples enhances the Clooney vibe). And, when he throws on a classic tuxedo for a fundraising gala—he’s the chair of the Toronto East ­General Hospital Board Foundation and the co-founder of True Patriot Love, an organization that supports military families—he earns double takes from pretty young things and society matrons alike.

The 43-year-old exec recently left Thornmark Asset Management for an e-commerce startup called AudienceView.

“The sophisticated and classic men of Hollywood: the Rat Pack, Cary Grant and Sean Connery.”

When it comes to feeling put together, Pierre Jutras has his routine down to a ­science: “A good night’s sleep, a great workout, a cold shower and a crisp suit.” As president of the Spoke Club, he spends most of his days in corporate attire but changes out of it the minute he gets home (his preference is jeans from Citizens of Humanity or Hugo Boss Orange, a V-neck pullover and high-end sneakers). His four-year-old son, meanwhile, embraces a more eclectic aesthetic and is eager to expand his fashion horizons. “Tristan’s mother became his personal stylist the minute he was born, but he has since developed his own style and frequently vetoes some of her choices,” says Jutras.

Pierre is the 40-something president of the Spoke Club. His son, Tristan, is four.

“Alain Delon, Cary Grant—I love the easy elegance of ’60s movie stars.”

As a kid, Sydney Berchtold was always dying to get into her three older sisters’ ­closets. Now she has the most covetable wardrobe of all—Rosedale’s The Narwhal boutique, where she stocks cool-girl lines like Helmut Lang, Acne and ALC—and where her sisters come for style advice. “I’m really bossy!” she says. “One is into boot-cut jeans, and I tell her she’s not allowed to wear them.” ­Buchkowsky, for her part, says she’s not as obsessed with clothes as you might expect (though her background is in buying and merchandising; Berchtold’s is interior design). “Marisa always looks badass,” says Berchtold, who thinks her partner’s edgy, street-style look complements her girly taste. “But Sydney is playful and adventurous,” says ­Buchkowsky, “and she has fun with every trend.”

Berchtold, 28, and Buchkowsky, 31, are the co-owners of The Narwhal boutique.

Berchtold: Jane Birkin, Kate Moss. Buchkowsky: the Olsen twins, the Rolling Stones.

Jimmy Molloy sells only the most ­spectacular houses and condos in neighbourhoods like Rosedale, Forest Hill and Yorkville. It’s a serious business, involving serious money, and he dresses the part: in impeccable pinstriped suits, he exudes the same aura of power as his high-profile clients. But Molloy distinguishes himself from the typical Bay Street types with the occasional lighthearted sartorial touch. He might sport rainbow-hued socks under his signature Gucci oxfords, for instance. Or, for a night out, he’ll throw on a superb aubergine Armani smoking jacket. You don’t spend 21 years married to Fashion magazine editor-in-chief Bernadette Morra without learning a few tricks.

The 54-year-old former restaurateur (he used to own the fine dining spot Auberge Gavroche) is one of Toronto’s top realtors.

“Colin Firth. He’s always elegant, but still relaxed and approachable.”

When Vanessa Morcom was 19, she preferred clothes that were short and tight and went well with a stiff drink. That’s not so unusual—but she also ran her own PR firm, handling press scheduling for Madonna, Rihanna and Drake. It was a life that proved as uncomfortable as a pleather mini, so at 24, Morcom chucked the company, volunteered with an NGO and relaxed. Now back in publicity, she likes clothes that are stylish but comfortable. “When I show up in my cowboy boots, black jeans and a crisp, white shirt, I’m there to get the job done, not to look the part,” she says. Kimono blazers and silk jumpsuits are easy staples for 18-hour days, and on weekends Morcom can be found in loose athletic wear, teaching yoga and meditation at the Toronto South Detention ­Centre. “Both in and out of work,” she says, “I’ve learned that you have to underplay it.”

The 29-year-old Morcom is the CEO of the publicity firm Morcom Media.

“Marchesa Luisa Casati, the Italian heiress and muse. I just feel her spirit.”