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

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

Toronto's Best Dressed 2014: our annual list of the city's most stylish people Chloe Rogers (Photograph by Norman Wong)
 

Toronto's Best Dressed 2014: The IT Girl Dress, Giambattista Valli Couture, The Room; earrings, J.Crew; bracelets and rings, Vita Fede, Intermix (Photograph by Norman Wong)
 
The IT Girl
Chloe Rogers

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.

Toronto's Best Dressed 2014: The Wonder Woman Cohon, at home in Rosedale, wears an Alexander McQueen jumpsuit and Tiffany and Co. jewellery (Photograph by Evaan Kheraj)
 
The Wonder Woman
Suzanne Cohon

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.

Vitals

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

Style Inspiration

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

Her Current Obsessions
Current Obsessions
Classy bangle
“I’ve always loved Tiffany’s Atlas collection.” Hinged bangle, $7,050. Tiffany and Co., 150 Bloor St. W.,
416-921-3900.
Suzanne Cohon: Current ObsessionsBlack jumpsuit
“I’m obsessed: anytime I see an interesting one, it’s added to the wardrobe.” 424 Fifth jumpsuit, $199. The Bay, 176 Yonge St., 416-861-9111.
Suzanne Cohon: Current ObsessionsTata Harper body oil
“I plow through the stuff.” Rejuvenating body oil, $90. Gee Beauty, 2 Roxborough St. W., 416-486-0080.
Current ObsessionsSuzanne Cohon: Current ObsessionsPractical shoes
“Vince Camuto’s booties are stylish, comfortable and don’t break the bank.” Klayton booties, $180. The Bay, 176 Yonge St., 416-861-9111.
Suzanne Cohon: Current ObsessionsChic trench
“I plan on wearing a Burberry trench over my leather jumpsuit.” Westminster trench coat, $1,850. Burberry, 144 Bloor St. W., 416-920-7717.
Mason, shown here at the Drake Hotel, wears a Davido Afnani suit and a K. T. Linens pocket square (Photograph by Evaan Kheraj) Mason, shown here at the Drake Hotel, wears a Davido Afnani suit and a K. T. Linens pocket square (Photograph by Evaan Kheraj)
 
The Silver Fox
Paul Mason

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.”

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Silver Fox
A fitted wool sweater
“I like simple pieces that don’t date.” $298. Club Monaco, various locations.
Current Obsessions: The Silver FoxHair gel
“I don’t use many grooming products. If I run out of this, I run hand moisturizer through my hair.” L’Oréal Indestructible hair gel, $8 Shoppers Drug Mart, various locations.
Current Obsessions: The Silver FoxSignature fragrance
“It’s a gentlemen’s cologne—clean and a little citrusy.” Penhaligon’s Blenheim Bouquet, $85. MenEssentials, 412 Danforth Ave., 1-800-833-1055.
Current Obsessions: The Silver FoxTan brogues
“You can’t go wrong.” Church’s wingtip brogues, $525. Gravitypope, 1010 Queen St. W., 647-748-5155.
Current Obsessions: The Silver FoxDark, fitted chinos
“I can pull off the best suits in the world, but I’m a chinos kind of guy.” $75. J.Crew, various locations.
Toronto's Best Dressed 2014: The Tomboy Lui, at the eTalk studios on Queen West, wears a Stella McCartney dress and Chanel shoes (Photograph by Evaan Kheraj)
 
The Tomboy
Elaine Lui

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.

Vitals

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

Style Inspiration

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

Her Current Obsessions
Current Obsessions: The Tomboy
Monogrammed pyjamas
“When I’m blogging at home, I’m in pyjamas. I’m very particular about them.” $112. J.Crew, Eaton Centre, 416-977-0941.
Current Obsessions: The TomboyDrop-crotch pants
“The drop-crotch elongates your body and hides problem areas.” Fidelity jeans, $210. Over the Rainbow, 101 Yorkville Ave., 416-967-7448.
Current Obsessions: The TomboyDenim jacket
“One item that’s impervious to those stupid fashion rules is the denim jacket. It never ages.” Rag and Bone jacket, $150. Rag-bone.com.
Current Obsessions: The TomboyConverse sneakers
“I have 15 pairs, maybe 20. They’re scattered on every floor of the house.” $74. Getoutside, 437 Queen St. W., 416-593-5598.
Current Obsessions: The TomboyA bright lip colour
“Vincent Longo’s Priscilla lipstick lasts forever and polishes my look.” Thinstick lipstick, $27. Vincentlongo.com.
Toronto's Best Dressed 2014: The Print Master Vann, photographed on King Street East, wears a Raptors cap, a Garrison Bespoke suit made with Holland and Sherry summer wool and Finsbury shoes (Photograph by Evaan Kheraj)
 
The Print Master
J.S. Vann

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.”

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Print Master
Flattering glasses
“These can really change or complete a look.” Warby Parker Haskell glasses, $120. Ca.warbyparker.com.
Current Obsessions: The Print MasterSoft navy jacket
“It goes over everything.” Jacket, from $1,200. Garrison Bespoke, 101-26 Wellington St. E., 416-566-2041.
Current Obsessions: The Print MasterBright shoes
“Purple, yellow, red; I love that pop of colour.” Gaziano and Girling Derwent fox suede shoes, from $1,600. Gazianogirling.com.
Current Obsessions: The Print MasterA signature scent
“My go-to is Tom Ford Oud Wood. It’s mysterious.” $225. Holt Renfrew, 50 Bloor St. W., 416-922-2333.
Current Obsessions: The Print MasterGreat clippers
“A well-groomed man needs a variety of clippers for a polished look.” Wahl Stainless Steel Lithium Ion, $70. Canadian Tire, various locations.
Toronto's Best Dressed 2014: The Sneaker Prince Burke, shot at the Thompson Hotel, wears a Strellson suit, Converse Chuck Taylors and a Chanel J12 watch (Photograph by Evaan Kheraj)
 
The Sneaker Prince
Jason Burke

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Sneaker Prince
Converse Chuck Taylors
“I switch to grey, black, or red if I feel like a pop.” $68. Little Burgundy, Eaton Centre, 416-260-0497.
Current Obsessions: The Sneaker PrinceDark suit
“I’ve bought them at Tom’s for 20 years—all I do is update the colour.” Strellson Rick James Suit, $650. Tom’s Place, 190 Baldwin St., 416-596-0297.
Current Obsessions: The Sneaker PrinceSkinny jeans
“I wore them every day for a year until they got a hole.” United Stock jeans, $160. Snkrbox.com.
Current Obsessions: The Sneaker PrinceOxford shirt
“Clean, simple, and I can carry my electronic devices around in the chest pocket.” $120. Snkrbox.com.
Current Obsessions: The Sneaker PrinceSturdy suitcase
“It fits my sneakers and their boxes.” Salsa suitcase, $599. Rimowa, 101 Bloor St. W., 416-922-2644.
Toronto's Best Dressed 2014: The Countess Corbo, pictured at home, wears a Vionnet skirt and shoes, and a Fausto Puglisi top. The handbag is also Vionnet (Photograph by Evaan Kheraj)
 
The Countess
Lisa Corbo

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.

Vitals

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

Style Inspiration

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

Her Current Obsessions
Current Obsessions: The Countess
Red lipstick
“Dolce and Gabbana makes the best lipsticks. I will never go back!” Monica Voluptuous lipstick, $33. Sephora, various locations.
Current Obsessions: The CountessSexy but understated pumps
“Shoes should be interesting but never overpower an outfit. I have the same stilettos by Gianvito Rossi in many colours.” From $640. Shop.gianvitorossi.com.
Current Obsessions: The CountessStatement dresses
“When you travel for work like I do, dresses are easy to pack. I love my pieces by Jason Wu, Ungaro or Altuzarra.” Altuzarra dresses, from $1,600. George C, 21 Hazelton Ave., 416-962-1991.
Current Obsessions: The CountessImpeccable bra
“A good-fitting bra is essential. My favourite is a lace number by Simone Perele.” Push-up bra, from $120. Melmira, 3319 Yonge St., 416-485-0576.
Current Obsessions: The CountessLoree Rodkin sunglasses
“I am addicted.” Miranda sunglasses, $950. Samaeyewearshop.com.
Toronto's Best Dressed 2014: The Marlboro Man Anderson, at Soho House on Adelaide, wears APC jeans, a Ralph Lauren corduroy shirt and a vintage leather jacket he discovered in the club’s lost and found (Photograph by Evaan Kheraj)
 
The Marlboro Man
Markus Anderson

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Marlboro Man
Grey sweats
“I’ve been wearing Roots sweats my whole life. I’ve never found anything as cozy.” Sweatpants, $50–$68. Roots, 100 Bloor St. W., 416-323-3289.
Current Obsessions: The Marlboro ManButton-down shirt
“Thom Browne’s are fitted without making you look like a sausage.” Thom Browne oxford, $285–$350. Contraband, 154 Cumberland St., 416-928-1414.
Current Obsessions: The Marlboro ManLeather clipper
“It’s been my carry-on for years—very English. It looks exactly the same 10 years later.” $2,050. Mulberry, 131 Bloor St. W., 944-8251.
Current Obsessions: The Marlboro ManRound sunglasses
“I discovered Moscot frames years ago and have them in six different colours and styles. Classic.” Frames, $240. Moscot.com.
Current Obsessions: The Marlboro ManLeather loafers
“You can wear them with jeans, shorts, suits—they look old-school. Mine are still beautiful, even after a decade of abuse.” NDC Made by Hand loafers, $197. Farfetch.com.
Toronto's Best Dressed 2014: The Office Hipster Affifi, shot in front of Roy Thomson Hall, wears head-to-toe Tiger of Sweden (Photograph by Evaan Kheraj)
 
The Office Hipster
Morad Reid Affifi

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Office Hipster
Flannel shirt
“It’s beaten up, fitted and really cool.” Flannel shirt, $170. Mooseknuckles.com.
Current Obsessions: The Office HipsterMykita Mylon shades
“My lenses are Zeiss—same as NASA uses. It’s a classic look with modern technology. Frames, $660. Josephson Opticians, 60 Bloor St. W. 416-964-7070.
Current Obsessions: The Office HipsterDark blazer
“When I wear a Tiger of Sweden blazer, I feel like I’ve got a custom-made jacket on. I have four of these.” Blazer, $559. Tiger of Sweden, 56 Ossington Ave., 416-588-4437.
Current Obsessions: The Office HipsterGrey suede shoes
“They’re super comfortable but still look great.” John Varvatos shoes, $698. Gravitypope, 1010 Queen St. W., 647-748-5155.
Current Obsessions: The Office HipsterBeard oil
“It smells really good. Softens the hair a bit. It’s almost like a cologne—but I don’t wear cologne.” $36. Provinceapothecary.com.
Toronto's Best Dressed 2014: The Playmates Posing on Portland Street: Violet’s outfit is from Advice From a Caterpillar, and her shoes are by Lilly New York. Misty wears a Mikhael Kale dress and J.Crew pumps (Photograph by Evaan Kheraj)
 
The Playmates
Misty Fox & Violet Keeler-Fox

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.”

Vitals

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

Style Inspiration

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

Their Current Obsessions
Current Obsessions: The Playmates
Cool play clothes
“Violet mixes them up with runners, jean jackets and some fraying tulle left over from her princess phase.” Skirt, $87. Advice From a Caterpillar, 8 Price St., 416-960-2223.
Current Obsessions: The PlaymatesPamela Love rings
“I work with and value my hands, so I dress them up.” From $125. Pamelalovenyc.com.
Current Obsessions: The PlaymatesChie Mihara heels
“The brand keeps impressing me with comfort and style.” $350–$500. Holt Renfrew, 50 Bloor St. W., 416-922-2333.
Current Obsessions: The PlaymatesViolet’s goggles
“She’s so mad about swimming that her goggles are usually on her head.” $25. MEC.ca.
Current Obsessions: The PlaymatesLeather pants
“I like the super-long, sexy versions from AllSaints and Citizens of Humanity.” $900. Allsaints.com.
Toronto's Best Dressed 2014: The Maestro Civello, in his Rosedale home, wears a Tom Ford suit, shirt, tie, pocket square and glasses, a Cartier watch and Tiffany and Co. cufflinks (Photograph by Evaan Kheraj)
 
The Maestro
Ray Civello

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Maestro
Green brogues
“Old women think they’re amazing, but so do 20-somethings.” Church’s brogues, $715. Gravitypope, 1010 Queen St. W., 647-748-5155.
Current Obsessions: The MaestroFrizz banisher
“Smooth Infusion Naturally Straight gives my curly hair a great wave.” $26. Aveda, 125 King St. E., 416-921-2961.
Current Obsessions: The MaestroSleek toiletry case
“I spend 50 per cent of my time travelling; Want’s kit is made for the busy flyer.” Kenyatta Dopp Kit, $200. Want Apothecary, 1070 Yonge St., 416-924-8080.
Current Obsessions: The MaestroA classic watch
“I’m fond of Cartier’s Santos 100.” $67,500. Cartier, 131 Bloor St. W., 416-413-4929.
Current Obsessions: The MaestroLuxurious shave cream
“When I do decide to shave, I need something that softens my beard and doesn’t leave ingrown hairs.” Pure-formance shave cream, $18. Aveda, 125 King St. E., 416-921-2961.
Toronto's Best Dressed 2014: The Natural Mielke, shown at Trinity Bellwoods Park, is wearing a Horses Atelier dress (Photograph by Evaan Kheraj)
 
The Natural
Elissa Mielke

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.

Vitals

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

Style Inspiration

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

Her Current Obsessions
Current Obsessions: The Natural
Black nail polish
“It makes me feel tough.” Nail polish in Black Lace, $6.50. Sephora, various locations.
Current Obsessions: The NaturalAll-natural toner
“I don’t like makeup, so I just treat my skin with this instead.” Thayers cucumber witch hazel toner, $12. The Big Carrot, 348 Danforth Ave., 416-466-2129.
Current Obsessions: The NaturalWeathered denim
“I love the worn-in look.” 1969 patch and repair sexy boyfriend jeans, $85. Gap, various locations.
Current Obsessions: The NaturalVanilla perfume
“I mix essential oils for fragrance, and vanilla is a nice base.” Eau de toilette, $15. The Body Shop, various locations.
Current Obsessions: The NaturalRare sunglasses
“My Henry Holland Le Specs sunglasses are the first designer item I’ve ever purchased.” From $150. Lespecs.com.
Toronto's Best Dressed 2014: The Pragmatist Chung, at Gotstyle in the Distillery District, wears a Suitsupply double-breasted corduroy suit, J.Crew shirt, Club Monaco tie, Cole Haan shoes and Bevel glasses (Photograph by Evaan Kheraj)
 
The Pragmatist
Lance Chung

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Pragmatist
Lapel accessories
“I love the whimsy of lapel accessories. I recently picked up a shiba inu pin from Lost and Found on Ossington.” $7. Lost and Found, 44 Ossington Ave., 647-348-2810.
Current Obsessions: The PragmatistSleek card holder
“If there’s one thing that I cannot stand, it’s a bulky wallet. I keep my cards and ID in this beautiful engraved silver card holder.” $32. Fineanddandyshop.com.
Current Obsessions: The PragmatistA handsome watch
“You can tell a lot about a man by the watch he wears.” Ferragamo 1898 Line watch, from $1,400. Salvatore Ferragamo, Yorkdale Shopping Centre, 416-787-4994.
Current Obsessions: The PragmatistA smart collection of ties
“Knits, patterns, prints—there’s much to choose from.” From $130. Gitman Bros., gitman.com.
Current Obsessions: The PragmatistA simple grooming regime
“I’m a fan of Dr. Bronner’s soaps.” $5. The Big Carrot, 348 Danforth Ave., 416-466-2129.
Toronto's Best Dressed 2014: The Bohos Lounging at home: Lola wears a Stella McCartney top, Zara skirt and cardigan, vintage boots, and an Urban Outfitters headpiece. Sacha wears a vintage dress she bought in Los Angeles and Balenciaga sandals. Her necklace was a gift from her mother (Photograph by Evaan Kheraj)
 
The Bohos
Sacha Grierson & Lola Flanery

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.”

Vitals

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

Style Inspiration

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

Their Current Obsessions
Current Obsessions: The Bohos
Essie nail polish
“Lola’s one beauty obsession is painted nails. Her colour du jour is A Cut Above.” $9. Tradesecrets.ca.
Current Obsessions: The BohosCashmere scarf
“I’ll wear it with Acne jeans and a Sundry tee.” $199. Club Monaco, various locations.
Current Obsessions: The BohosJo Malone Pomegranate Noir
“I only feel complete once I have my fragrance on.” Jo Malone perfume, $136. Holt Renfrew, 50 Bloor St. W., 416-922-2333.
Current Obsessions: The BohosAkid shoes
“Lola can climb trees in them—which is really how we should all measure a good shoe.” $70. Akidbrand.com.
Current Obsessions: The BohosGold high-heeled sandals
“The mix of skin and straps is the best.” Louboutin sandals, $895. Net-a-porter.com.
Toronto's Best Dressed 2014: The Leading Man Burns, at Toronto East General Hospital, wears a Gotstyle jacket, Duchamp London shirt, Paul Betenly pants and Prime shoes (Photograph by Evaan Kheraj)
 
The Leading Man
Michael Burns

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Leading Man
Masculine bracelet
“I even wear it with a suit.” Miansai bracelet, $115. Elevator, 1273 Queen St. W., 416-535-9671.
Current Obsessions: The Leading ManCozy scarf
“Brunello Cucinelli makes a great one that I wear with a peacoat.” Cashmere scarf, $595. Brunellocucinelli.com.
Current Obsessions: The Leading ManMoney clip
“I often use a Tiffany money clip—but I would resort to a paper clip in a pinch.” Paloma’s Caliper clip, $400. Tiffany and Co., 150 Bloor St. W., 416-921-3900.
Current Obsessions: The Leading ManSturdy boots
“There’s nothing better than slipping on a pair of Frye boots, especially if you’re going for the urban cowboy look.” Frye Harness Boots, $180. Ron White, Manulife Centre, 416-964-6400.
Current Obsessions: The Leading ManSlick cufflinks
“I have an enormous collection.” Eyecandy cufflinks, $65. Cuffwear, 993 Queen St. W., 416-306-0031.
Toronto's Best Dressed 2014: The Dandies Pierre, photographed at his east-end home, wears a Marlon Durrant custom shirt, Gotstyle vest and pants, Happy Socks socks and custom shoes by Atelier de L’Egide in Montreal. Tristan wears a Jacadi shirt, shoes and pants, Gap Kids vest, and Joe Fresh hat and scarf (Photograph by Evaan Kheraj)
 
The Dandies
Pierre & Tristan Jutras

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.

Vitals

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

Style Inspiration

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

Their Current Obsessions
Current Obsessions: The Dandies
A boho vest
“Tristan likes layers. He describes his style as ‘pirate.’” Vest, $82. Jacadi, 87 Avenue Rd., 416-923-1717.
Current Obsessions: The DandiesBrightly patterned socks
“They add vibrancy to a classic look.” $12. Getoutside, 437 Queen St. W., 416-593-5598.
Current Obsessions: The DandiesA fitted ultramarine suit
“Like something Jean-Paul Belmondo would wear.” Ollie suit, $878. Tiger of Sweden, 56 Ossington Ave, 416-588-4437.
Current Obsessions: The DandiesDesigner sneakers
I love Sully Wong sneakers for their comfortable, retro feel.” $160. Sullywong.com.
Current Obsessions: The DandiesNatural beachy hair
“Trying to put product in Tristan’s hair is an epic battle.” Aveda Be Curly enhancer, $24. Aveda.com.
Toronto's Best Dressed 2014: The Shopgirls Buchkowksy (left) wears a Rag and Bone hat, Iro jacket and booties, and a Raquel Allegra dress. Berchtold wears a skirt and top by ALC, Rag and Bone sandals, and jewellery by Pamela Love, Grace Lee and Finn NY. The women are photographed in The Narwhal boutique (Photograph by Evaan Kheraj)
 
The Shopgirls
Sydney Berchtold & Marisa Buchkowsky

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.”

Vitals

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

Style Inspiration

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

Their Current Obsessions
Current Obsessions: The Shopgirls
Black leather booties
SB: “These classics by Rag and Bone will carry you from day to night.” $525. The Narwhal, 8 Price St., Unit 101, 647-351-5011.
Current Obsessions: The ShopgirlsSkin care with active ingredients
SB: “Gee Beauty has changed my skin. I love the lactic acid in this corrective serum.” $105. Gee Beauty, 2 Roxborough St. W., 416-486-0080.
Current Obsessions: The ShopgirlsRosy blush
MB: “It makes me look fresh.” Nars blush, $33. Holt Renfrew, 50 Bloor St. W., 416-922-2333.
Current Obsessions: The ShopgirlsBig leather bag
MB: “It holds my life!” Jerome Dreyfuss Florent backpack, $1,127. Farfetch.com.
Current Obsessions: The ShopgirlsStatement jacket
MB: “The star.” Acne jacket, $650. The Narwhal, 8 Price St., Unit 101, 647-351-5011.
Toronto's Best Dressed 2014: The Gentleman Molloy, at home in the Annex, wears a Brooks Brothers tux and pocket square, Prada shoes, Paul Smith socks, Lindberg glasses, and Tiffany and Co. cufflinks (Photograph by Evaan Kheraj)
 
The Gentleman
Jimmy Molloy

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.

Vitals

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

Style Inspiration

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

His Current Obsessions
Current Obsessions: The Gentleman
Gucci loafers
“They’re fabulous with jeans and a cashmere sweater. Looking presentable makes all the difference.” Horse bit loafers, $590. Gucci, 130 Bloor St. W., Ste. 102, 416-963-5127.
Current Obsessions: The GentlemanSimple polo
“Joe Fresh polos are great value.” Classic polo, $12. Joe Fresh, 589 Queen St. W., 416-361-6342.
Current Obsessions: The GentlemanBulgari green tea shampoo
“It’s carried at some of the best resorts in the world, so I feel like I’m on vacation when I use it.” $49. Sephora, various locations.
Current Obsessions: The GentlemanCashmere sweater
“A necessity for fall evenings.” V-neck cashmere sweater, $100. Uniqlo.com.
Current Obsessions: The GentlemanRugged jacket
“It’s great for storing keys and has a special pocket that keeps cellphone radiation contained.” Loro Piana jacket, $6,450. Via Cavour, 87 Avenue Rd., 416-925-1866.
Toronto's Best Dressed 2014: The Fearless Femme Morcom, at Casa Loma, wears vintage kimono and jewellery (Photograph by Evaan Kheraj)
 
The Fearless Femme
Vanessa Morcom

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.”

Vitals

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

Style Inspiration

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

Her Current Obsessions
Current Obsessions: The Fearless Femme
Kimono jacket
“It’s how I imagine satin sheets to feel—so why not wear bedding all day if that’s what you long for?” Filippa K jacket, $350. Filippa-k.com.
Current Obsessions: The Fearless FemmeGraphic T-shirts
“I love my commemorative Basquiat T-shirt. It’s a collaboration with the MoMA—affordable high art.” T-shirt, $20. Uniqlo.com.
Current Obsessions: The Fearless FemmeLavender eye mask
“I’m a terribly nervous flyer. The smell of lavender calms me.” Eye mask, $85. Holisticsilk.com.
Current Obsessions: The Fearless FemmeHanae Mori perfume
“This soft scent has been my signature for more than 10 years.” $100. Sephora, various locations.
Current Obsessions: The Fearless FemmeLaptop case
“It’s my on-the-go, Japanese-inspired hardware protection, and it doubles as a clutch.” Modako laptop case, $100. Wearemodako.com.