Toronto is a good-looking town, with no shortage of beautiful people in beautiful clothes. But only a few are bona fide head-turners: city characters who take fashion to the next level. We celebrate them with our second annual list of Toronto’s best dressed.
Occupation: Chef and owner, The Harbord Room.
Stomping grounds: “Fiesta Farms in the Annex—the No Frills of gourmet food. Otherwise, my social life suffers because the restaurant keeps me busy. Thankfully, my friends come over to my place.”
Look: “Dishwasher chic. I spend 95 per cent of my time in clogs and an apron.”
Style philosophy: “Never wear shoes that form a point.”
Fall must-haves: “Thick and cozy wool knit sweaters from Rag and Bone, and a tweed vest.”
Obsession: “Custom suits made at Garrison Bespoke.”
Can’t live without: “My bathrobe. I’m a man of leisure at heart.”
Inspiration: “Larry David. On the inside, too.”
Signature scent: “Onions, garlic and Febreze. Works just fine.”
He’s wearing: Garrison Bespoke shirt and blazer, Vince pants, Sartorial tie, John Varvatos shoes, Stolen Riches laces.
Occupation: He’s the Joe in Joe Fresh.
Stomping grounds: Home is Forest Hill. “I’m also a regular at Sotto Sotto.”
Look: Sartorialist with an edge.
Style philosophy: “Less is more. Focus on the fit, shape, stitch detail and hand feel—properly executed, they will elevate the product.”
Fall must-have: “What’s more elegant than a simple white shirt? I have mine custom made by one of my suppliers.”
365 style: “I like to ensure that silhouettes are up to date. I prefer much slimmer, shorter pants, and jackets with a sharp lapel, slim arms and soft shoulders. And from April to October, I’m not wearing socks.”
Inspirations: “The enduring styles of the movies, particularly the ’50s and ’60s. Blow-up inspired my fall collection.”
Signature scent: “I’ve been wearing Gucci Pour Homme forever. It’s discontinued now, but I’ve found a ton on websites like fragrance.com. I’ve stocked up for the next couple of years.”
He’s wearing: Garrison Bespoke suit, Hermès belt, vintage 1960s sunglasses.
Occupation: Executive vice-president, in charge of international film sales at Entertainment One.
Stomping grounds: The Annex and every film festival.
Look: “I’m drawn to the gamine and the Edwardian—peplums, kitten heels, hoops on skirts and Liberty of London. I just bought Liberty-print Dr. Martens!”
Style philosophy: “Take pleasure in dressing, and with that, try to give others pleasure.”
Fall must-haves: Cocoon coats and velvet skirts by Thomas Tait. “Reminds me of Romeo Gigli.”
Inspirations: “The wonderful artist Christine Davis, the amazing hairstylist Bill Angst and the smart and fabulous Inès de la Fressange.”
At home: “I call my apartment the Museum of Charlotte, to warn civilians of my collections. I like shoes and possess many. I’ve rediscovered Hermès silk scarves, and I collect accessories by the Danish designer Charlotte Sparre.”
Signature scents: “Narciso Rodriguez for Her. I also have a soft spot for old, powdery Guerlain scents.”
She’s wearing: Prada dress, Cartier glasses, Falke tights.
Stomping grounds: “I’m a foodie and a bit of a wine snob, so I cook at home in King West, or eat out at The Ace in Roncey or Terroni on Queen.”
Look: “Timeless, in that I love to wear suits and ties. I follow the styles of the moment, but not too over-the-top. So when paisley was in, I wasn’t wearing paisley.”
Style philosophy: “Dress for the occasion.”
Fall must-have: A lightweight, preferably checkered gentleman’s scarf.
On getting ready to go out with his wife, Sarah Slean: “We definitely don’t need to hold items up and ask, ‘Do these match?’ We have similar aesthetics and we never clash. We always look good.”
Signature scent: “Old Spice deodorant.”
Inspiration: “Hollywood old guard: Gene Kelly. His style was amazing.”
He’s wearing: Farley Chatto shirt and windowpane-check jacket, Fidelity jeans.
Occupation: Musician, artist.
Stomping grounds: “I’ve always been a west-ender, but there are so many pockets of Toronto I adore.”
Look: “A somewhat nerdy poetess inspired by fearless glamour.”
Style philosophy: “If it turns up your wattage, buy it.”
Fall must-have: “A sweater that wraps and ties up at the front—it’s like being hugged all day long.”
Inspiration: “Women who dare to be themselves in a culture obsessed with how they look.”
She’s wearing: Farley Chatto top and pants, Swarovski bracelet, vintage earrings.
Occupation: “Shop boy, glamour enabler and creative director of The Room at The Bay.”
Stomping grounds: Home is Yonge and St. Clair. “Where do I hang out? I don’t hang out!”
Look: “Preppy and all-American, but I prefer a European cut.”
Style philosophy: “I find something I like and I stick to it to the point of being repetitive. I wear things to death, so the pieces have to be versatile—navy jacket, blue jeans, crisp shirts and bow ties. Novelty in shoes is key, as are colour and texture.”
Fall must-have: “The classic moderns and separates from Patrick Grant’s E. Tautz line.”
Inspirations: Cary Grant. “I also like the younger musicians—well, young to me. Jay-Z is super chic.”
Evening staple: “A good tuxedo with a two-button jacket and a peaked lapel.”
Cocktails of choice: A Park Hyatt roof bar Hendrick’s gin martini with an eighth of vermouth and olives. Or an Aperol spritz at Bar Centrale. “So many bars, so little time!”
He’s wearing: Cutler and Gross glasses, Gucci by Tom Ford jacket, Hugo Boss shirt, Tom Ford bow tie, Lanvin pocket square.
Occupation: Musician and fashion stylist.
Look: Jekyll and Hyde–ish. “One day I’ll be a gypsy, the next a sports guy, the next a Bay Street banker.”
Stomping grounds: “Scarborough, midtown and Queen West.”
Style philosophy: “Wear it once, wear it twice, switch it up and wear it thrice. In other words, never give anything away.”
Fall must-have: Quality boots—that one pair you can dress up or down for any occasion.
Obsession: “Prints! They can be gingham, Hawaiian, plaid or tribal. I just can’t get enough—put me in printed fabrics from head to toe and I’ll be happy for the rest of my life.”
365 style: “I wear my Army Surplus boots in the winter and summer, untied if I’m feeling grungy.“
Inspiration: “My mother, Brigitte, was a fashion plate in her youth and has managed to pass her eccentric style on to me.”
He’s wearing: Bape print pants, H&M shirt, vintage lion necklace, Swatch watch, Max Azria cuff bracelet, Supreme sunglasses, Pamela Love rings.
Age: In her 60s. “I want to keep it magical and secret.”
Occupation: Sales consultant, Dolce and Gabbana at Holt Renfrew.
Stomping grounds: Leaside.
Look: Statuesque in couture.
Style philosophy: “Nothing conventional. Everything with a twist.”
Fall must-have: “I want to move away from black, so I’d like to own several pairs of slim indigo pants.”
Inspiration: “I’ve taken fashion risks since I was 14, but I’m not the most stylish person in my family; my father was. I remember gazing in awe at a red party dress in a shop window, and my father bought it for me for my 15th birthday. It was a magic moment.”
Wardrobe staple: A black leather jacket.
Signature scent: I have always worn Angel by Thierry Mugler. My sister told me that when I leave a room, the flowers leave with me.”
She’s wearing: Jean Paul Gaultier dress, Céline shoes, Lanvin bracelet, string jade bracelet made by a friend.
Occupation: Co-founder of the iconic media-based artist collective General Idea, and professional “healer.”
Stomping grounds: Jarvis and Gerrard.
Look: Magisterial shaman.
Style philosophy: “Wear your heart on your sleeve.”
Fall must-have: “A bespoke suit from Arnys, the menswear store in Paris that has been purchased (and will be closed) by LVMH.”
In memoriam: “The story of shopping in Toronto is a litany of places long gone or moved: I still have Pantherella socks that I bought on sale at Perry’s in the Colonnade on Bloor, as well as Yohji Yamamoto from Mari, and Issey Miyake from Yushi.”
Inspiration: Mark Jan Krayenhoff van de Leur. (They met at Bronson’s 50th birthday party in the Colonnade and have been together since.)
Evening attire: “Formal. It’s usually minimalist, but often over-the-top and probably black, like an Issey Miyake jacket.”
What he’s wearing: Carpe Diem shirt, pants and boots, Yohji Yamamoto black shirt, Bless scarf, bag from Arnys.
Look: European tailoring meets Midnight Cowboy couture.
Style philosophy: “Buy good designs and wear them for a long time. Never mind the trends.”
Fall must-have: “Four of my suits, including a gold-check Thierry Mugler, have worn out recently, leaving shirts and ties orphaned. I need to replace them.”
Day and night: “I have two distinct sides to my wardrobe. For work, it’s colourful, avant-garde formal, like Ozwald Boateng. I wear very specific combinations of patterns, colours and styles. For evening, I go for more conceptual designers like Margiela, Miyake and Yamamoto.”
He’s wearing: Levi’s and Mohawk deerskin jackets, Alexander McQueen shirt, custom Martin Margiela jeans, vintage belt, Comme des Gar.ons shoes.
Occupation: Artistic director, Toronto International Film Festival.
Stomping grounds: Trinity Bellwoods, Roncesvalles, TIFF Lightbox.
Look: “1962, with occasional reckless flashes of 1972, 1982 and 2012.”
Style philosophy: “Like most grown-ups, I’ve spent years figuring out what I like and what I don’t. When I see dudes strolling in capri pants, I know that’s not me.”
Fall must-have: “A pair of shiny black oxfords that I can walk in for 17 hours a day.”
Inspirations (art): “Tony Leung in the films of Wong Kar Wai; Sidney Poitier in his buttoned-down ’60s heroism. Even Tom Cruise wore great suits in Mission: Impossible 4, proving a good Super-200 fabric can stand up to global annihilation.”
Inspirations (life): “All the Caribbean men who stepped off the ships in 1950s England in sharp suits and hats pitched just so. They wore uniforms during the week, badass slippery shirts on Saturday nights and cricket whites on Sundays.”
Obsession: “I collect watches, but I’m the opposite of a watch snob. One of my favourites is a surprisingly reliable imitation of an Italian beauty that I found in Istanbul’s Grand Bazaar.”
Signature scent: “I never developed a taste for cologne. I prefer the scent of a woman.”
He’s wearing: Hugo Boss.
Occupation: Student and editor of Rostam magazine.
Stomping grounds: “Ella’s Uncle or Sam James for coffee; Saving Grace for brunch; Delux for dinner; Stella Luna, I Miss You, Penny Arcade, TNT and Holt Renfrew for shopping.”
Look: “Iranian gamine: masculine-feminine without looking butch.”
Style philosophy: “Looking put together should not take hours, or a fortune, to achieve.”
Fall must-have: A black turtleneck. “Because it looks killer with high-waisted black jeans and low-heeled black boots.”
Obsession: Sunglasses—currently, her Jason Wu tortoiseshell cat’s-eyes with light purple lenses. “I feel strong and slightly pervy when I wear them.”
Inspiration: “Men and women who have effortless swagger, without being overly accessorized.”
She’s wearing: Jason Wu glasses, Rag and Bone jeans, Lacoste turtleneck, Ann-Sofie Back coat.
Occupation: Fashion assistant and photographer, vintagecouture.com.
Stomping grounds: Parkdale and watering holes like Bambi’s on Dundas West.
Look: “Technical and instinctual. I enjoy the movement and texture of clothing made out of contemporary materials.”
Style philosophy: “Emulate six-year-olds. They dress up in whatever they want and have fun with it.”
Fall must-have: Jeremy Laing’s velvet pieces and Céline sweaters with fur and leather panels.
Can’t live without: “My 12 pairs of Céline shoes.”
Quality matters: “I hoard mint-condition vintage like it’s a treasure chest of gold.”
Inspirations: “Lee Miller, old Helmut Newton photographs, Monica Vitti in Antonioni films.”
She’s wearing: Denis Gagnon bralet, J. W. Anderson sweater, Michael Angel jacket, Céline pants, vintage Rolex, homemade furry bracelet, beaded Isabel Marant bracelet, Louis Vuitton shoes.
Occupation: Designer and blogger, Beckerman Bite Plate.
Stomping grounds: “I can always be found at Yorkdale. I’m a total mall rat—it’s almost a problem.”
Look: Surfer meets cowgirl meets rock star.
Style philosophy: “When in doubt, go funky.”
Fall must-have: Chloé studded motorcycle boots.
Obsessions: “Vintage Mickey Mouse rings and pink dip-dyed hair that reminds me of Jem. And I go Balenci-gaga for Balenciaga bags.”
Inspiration: “Our friend and muse Agyness Deyn, who dresses so fierce. Also, of course, my family.”
Fashion 911: “What do you do if your Chanel light bulb shoes burn out and refuse to turn on? First, you freak out a little, and then you call in an amazing electrician named Vladimir. He took them home, worked on them for eight hours straight and drove two hours to a specific store to get the correct bulb. He’s our hero.”
She’s wearing: Prada bag and furry scarf, Proenza Schouler shirt and skirt, Balenciaga belt, Isabel Marant necklace, Marques’Almeida leg warmers, Burberry Prorsum platform boots.
Occupation: Mother of three.
Stomping grounds: Home in York Mills with her daughters and her husband, Bob.
Look: “My girls call me a rock ’n’ roll mama.”
Style philosophy: “Collect anything with studs or fringe.”
Fall must-have: Isabel Marant Dicker boots, anything from the Marc Jacobs fall collection.
Favourite fashion memory: “When the girls were little, they dressed up in my workout leotards, sweatbands and leg warmers—the leotards came down to their knees—and jumped up and down on my bed singing ‘Beat It.’ ”
Obsessions: “Handbags that are light and don’t hurt my shoulders, like my Balenciaga city clutch.”
She’s wearing: Balenciaga vest, Proenza Schouler dress and bag, Chanel gloves, Wolford tights.
Occupation: Designer and blogger, Beckerman Bite Plate.
Stomping grounds: “Starbucks, Fabbrica, Holt Renfrew, The Room, Jonathan and Olivia, flea markets and vintage fairs.”
Look: “A combo meal. A little of this, a little of that—plus a surprise. My hair and makeup, however, stay the same: red lips, black ticks on the eyes, surfer hair.”
Style philosophy: “Try a million different things, and dress up even if you’re going for a root canal.”
Fall must-have: Isabel Marant western booties.
Obsessions: Faux fur, Essie nail polish and sunglasses—either cat’s-eye pearl or diamanté from A-morir.
The hat thing: “I have quite the collection—studded hats, toques, cowboy hats and even a knit beekeeper’s bonnet. We put them on our dogs.”
Inspirations: “My mom, twin sister, Samantha, and little sister, Chloe—they rock it like no other.”
She’s wearing: Prada coat and bag, April 77 x Calla jeans, David Cohen hat, Eddie Borgo and vintage bracelets.
Occupation: Textile designer at Juicy Couture.
Stomping grounds: West Hollywood; Yorkville when she’s home.
Look: “A downtown mash-up of pin-up and tomboy.”
Fall must-have: Rachel Comey leather booties.
Style philosophy: “Lots of colour and playfulness.”
Obsessions: “I collect skull paperweights and skull jewellery—they’re good luck—plus vintage southwestern jewellery, platform shoes, fun fur and fuzzy stickers.”
Fashion faux-pas: “Showing up to the father-daughter dance at Branksome Hall in punk costumes. For some reason, I thought it was themed. My dad wore an orange Mohawk wig and leopard bell-bottoms. Everyone else was in suits and dresses.”
She’s wearing: Vintage sweater, H&M hat and bracelets, Topshop skirt, Balenciaga shoes, Chanel handbag.
Occupation: Editorial director and co-founder, Plaid magazine.
Stomping grounds: Lives at Yonge and St. Clair, plays on Queen and Dundas West.
Look: Psychedelic meets 1950s.
Style philosophy: “Have a wardrobe that makes people smile. I’m a magpie for quirky pieces—rhinestones, interesting cut glass, animal and floral prints.”
Fall must-haves: Tons of blazers and cardigans—“because they style the outfit.”
Inspirations: “Roxy Music, David Bowie and Jimi Hendrix inspire me to put my best looks together.”
Wardrobe staple: A pink wool day dress with pockets and a cowl neck by Dominic Rompollo over a blouse or on its own. “The subtle detailing is absolutely perfect.”
She’s wearing: Vintage necklace, brooch, blouse, skirt and brogues, Club Monaco blazer.
Occupation: PR and social media manager of eLuxe.
Stomping grounds: Queen West.
Look: Bauble-loving modernist.
Style philosophy: “If you won’t feel confident in it, don’t bother putting it on.”
Fall must-have: A bootie with a heel.
Fashion hero: Taylor Tomasi Hill, artistic director of the luxury online retailer Moda Operandi. “She dresses as if she doesn’t care what anyone thinks.”
Family values: “Growing up with two sisters, I realized that nothing lasts forever. Clothes either get worn out or go missing, so I’ve learned not to get attached to anything. Except for my gold and costume jewellery. I build my outfits around it.”
Signature scent: Bal d’Afrique by Byredo. “Ben Gorham, Byredo’s artistic director, picked it out for me. I sprayed it once, and it smelled wonderful.”
What she’s wearing: Vintage camo jacket, Zara skirt, Sachin and Babi shirt, W.I.S.H. Creatively necklace, bracelets by J. Crew, Madewell and Fenton.
Occupation: “Photographer, society blogger, flâneur.”
Stomping grounds: Yorkville.
Look: “Androgynous, defiant and generally impractical.”
Style philosophy: “Dressing is more about discipline than anything else. I make the same effort to dress up in the daytime as I do at night.”
Fall must-have: Black cashmere turtleneck.
Can’t live without: “A fur coat. A fantastic coat can hide a multitude of sins.”
Inspirations: “The social luminaries of parties past: Babe Paley, Millicent Rogers, Gloria Guinness and Nan Kempner. These high-society doyennes were masters of using clothes to craft a persona.”
He’s wearing: Dries Van Noten pants, Prada shoes and sweater, 1960s Tricosa coat, Mark Lash diamond and platinum cuffs, Mark Lash diamond and emerald ring.
Occupation: Director of branding at Mantella Corporation, socialite.
Stomping grounds: Thornhill. “And from spring through fall, it’s hard to beat the patio at La Société for people watching.”
Style philosophy: “It’s all about fit! More than half of my wardrobe is tailored to me on some level. My seamstress and I see each other on a regular basis. When a piece hugs your body in all the right places, you immediately feel beautiful.”
Fall must-haves: “I love velvet, and I can’t resist a pair of knee-high boots with a very high heel in any deep tone.”
Collections: Vintage evening gloves. “From delicate lace ones to beyond-the-elbow satin—a pair in every colour.”
Style icons: The Elizabethans. “Their look was spectacular, opulent and precise—but I know it isn’t practical.”
Signature scent: Spring Flower by Creed. “Occasionally I’ll mix in a little Lolita Lempicka, and the result is delicious.”
She’s wearing: Michael Kale gown, Louboutin shoes, one Cartier bangle for each of her three kids.
Occupation: Hairstylist and makeup artist.
Stomping grounds: “Walking along Queen West beats reading any fashion blog.”
Look: Contemporary lines, statement hair.
Style philosophy: “I don’t repeat pieces, but I use everything I own. Too much of one thing seems, frankly, wasteful.“
Fall must-have: A chunky black cardigan.
Wardrobe staple: “A coworker gave me a strand of black Buddhist prayer beads. I’m not Buddhist, but I feel that they bring me good luck.”
Fashion charity: “I’ve been known to give Vivienne Westwood to Goodwill.”
Signature scents: Coromandel and Sycomore, both Chanel.
He’s wearing: Jeremy Laing jacket, Rag and Bone shirt, All Saints jeans, vintage and Links of London bracelets, Dr. Martens boots.
Stomping grounds: Bloorcourt Village.
Occupation: Fashion stylist, vintage retailer on Etsy, art student.
Look: “Witchy ’90s schoolgirl flower child who wishes she had a motorcycle.”
Style philosophy: “I get a kick out of creating an image that’s beautiful, thought-provoking and somewhat bizarre.”
Fall must-haves: Harley Davidson T-shirts, art books and leather.
Inspirations: “I find it everywhere, from my friends to my cats to books like Alice’s Adventures in Wonderland, which made me obsessed with flouncy skirts.”
I’m not above wearing: “Microscopic denim shorts to school (oops).”
She’s wearing: Chloé Comme Parris leather shirt and rings, vintage dress, American Apparel underskirt, Lara Vincent flower headpiece and vintage jewellery.
Occupation: Artistic director, Luminato.
Stomping grounds: The Annex, Harbord Room, Sotto Sotto. “And the back of our house with a gin and tonic.”
Look: “Sophisticated-boring with a touch of extravagance.”
Style philosophy: “How you move in your clothes is more important that what you wear.”
Fall must-have: A yellow raincoat. “In German, it’s called a friesennerz.”
Inspiration: “Jean-Paul Belmondo for his laid-back, brutal elegance.”
Controlling influence: “My fiancé, Rufus Wainwright. Before we go out, I always need his judgment. He usually adds a brooch, a scarf, or even a Tarot card with a pin to inject a bit of sparkle.”
Facial hair: “I’ve tried out all shapes, lengths and moustaches.”
On the inside: “I wish I could live without underwear, but I hardly ever like the no-underwear feeling. I read somewhere that people who don’t wear underwear are more successful. I’d rather wear jock straps than boxers. It’s the same for bathing suits: Speedos, not those awful surfer shorts.”
He’s wearing: Yohji Yamamoto scarf, Claudia Skoda sweater and pants, Martin Margiela boots. The carnelian ring is a gift from designers Viktor and Rolf.
Occupation: Owner, 69 Vintage.
Stomping grounds: “I’m a creature of Queen West, so I like morning coffee meetings at White Squirrel, lunches at Luna and wine-paired dinners at Local Kitchen. Parts and Labour does a great French 75; it’s my favourite champagne cocktail.
Look: “Unpredictable. My style and taste are in constant motion.”
Style philosophy: “Anyone can pull off any outfit—you just have to put it on to pull it off.”
Fall must-haves: Camilla Skovgaard boots with a sturdy heel, heavy wool winter-white button-fly work pants, and lots of cashmere.
Prized collection: Her Edwardian and Victorian antique white cotton lace and crochet textiles.
Inspiration: Historical books. “I could see a 1920s photo of a female athlete in a wool jersey or golf attire, and it could influence my wardrobe for the season.”
Signature scents: “Rose water and fresh air.”
She’s wearing: Vintage dress, cape and bracelet, Camilla Skovgaard boots.