These 22 sartorial heroes have a passion for fashion and a rare talent for putting together outfits that make heads turn—and this, more than anything, is a reason to celebrate them
The 25-year-old entrepreneur will launch her fashion site InSepia Inc. in October.
“As Diana Vreeland said, ‘The only real elegance is in the mind; if you’ve got that, the rest really comes from it.’ ”
“Two-toned leather brogues by Bally.”
“When I worked at vogue.com, I spilled coffee on a 3.1 Phillip Lim dress I’d borrowed from the Vogue closet to wear to the Met Ball. I was so worried. When I returned it in a dry-cleaning bag, the fashion associate laughed, saying it was just an old sample.”
Tevrow and Chase coat, Rag and Bone pants, Stuart Weitzman booties.
The 34-year-old MPP for Bramalea-Gore-Malton lives in Derry West Village, Mississauga.
“Bespoke with a splash of fun.”
“Don’t over-follow trends. Keep the trendy items to an accessory or a highlight of the outfit.”
“Tom Ford’s suits for their powerful lines. But most of all, I’m obsessed with artisans, the idea of handmade things and how they’re perfection and imperfection at the same time.”
“Suits from Trend Custom Tailors and Garrison Bespoke, plus colourful turbans and pocket squares. Fashion is both social armour and a barrier breaker—if I’m wearing a bright turban, for example, it’s a conversation starter.”
“For breaking into fashion, the Punjabi-American actor and jewellery designer Waris Ahluwalia.”
“A handmade briefcase—I’m searching for the right style. And it’s not fall-ish, but I’m looking to buy a Moto Guzzi motorcycle and a Jaeger-LeCoultre timepiece.”
Garrison Bespoke tweed blazer, custom-made oxford shirt and trousers, Dion silk pocket square, Rolex watch.
The 37-year-old owner of I Miss You Vintage (and her five-year-old son, Jamie) are fixtures on Ossington
“I’ll be glamorous with an edge today, dark minimalist tomorrow, but I’m always ‘cool mom.’”
“Wear what suits you because it suits you, not because someone tells you it does.
“My 1963 Thunderbird.”
“I love fashion history—Thierry Mugler, 1980s Azzedine Alaïa and Alexander McQueen, to name a few. I never get bored of looking at my collection of vintage fashion magazines, like Vogue, Delineator, Glamour, Harper’s Bazaar and L’Officiel.”
“I’m asking the vintage gods to bring me something from the ’30s or ’40s in black velvet with metallic embroidery and beads à la Balmain.”
Herve Leger dress, H&M ring, Jeffrey Campbell heels.
H&M jeans and oxfords, Zara vest and hat, vintage jacket and belt.
Formerly of Fashion magazine and eLuxe, the 54-year-old Sheffman is now one of the city’s top freelance creative directors and stylists.
“Relentlessly casual, boyish and devoted to comfort.
“Playing tennis and learning to play the cello.”
“Men’s cardigans and loafers, white V-neck and black-and-white striped tees, skinny jeans, pencil skirts, my tennis skirt, anything in grey cashmere.”
“There’s a full-on carnival in my head. Photo shoot ideas strike in the shower, on my spin bike—anything, anytime, anywhere.”
“The search for the perfect flat black bootie continues.”
Joe Fresh shirt, The Row jacket, Citizens of Humanity jeans, Baume and Mercier watch, Brioni necklace, Carole Tanenbaum vintage bracelet, Jean-Michel Cazabat pumps.
The 31-year-old is a designer collections buyer at Harry Rosen.
“A friend described me as ‘like a buyer at Pitti Uomo [the defining menswear trade show, held in Florence], but more badass.’”
“Dress for how you want to tackle the day—if you want to do something boldly, dress bold.”
“Zegna designer Stefano Pilati, whose work is both architectural and fluid, and the brilliant Vogue Italia editor Franca Sozzani.”
“Crisp white dress shirts. You can never have enough.”
“Chunky cardigans and a black shearling bomber jacket, both from Ralph Lauren’s black label.”
Dolce and Gabbana shirt, Danier jacket, Zegna scarf and trousers.
The 28-year-old vintage lover runs the Etsy store InPastTimes.
“The older the better.”
“Two-tone leather saddle shoes, oxfords and loafers.”
“Big, bright and bold vintage costume jewellery.”
“Black and white movies, cheesy musicals, mid-century department store catalogues and re-runs of The Price is Right from the ’70s. I find inspiration on lookbook.nu—it’s a great way to see what people are wearing all around the world—and shorpy.com, which showcases real photographs from the 1850s to the 1950s that depict everyday life and fashion.”
“I’m wearing socks with my sandals right now.”
1960s Eaton’s faux leopard coat, vintage pink dress and jewellery, bird’s nest brooch that she made. She’s holding her Yashica Mat-124G TLR camera.
The 32-year-old tailor and men’s stylist owns Garrison Bespoke.
“Sharply tailored with a Canadian twist.”
“Always keep your jacket buttoned.”
“Deconstructed suits. I make them in lightweight tweeds and washed fabrics, without shoulder pads or lining, which creates a tailored look but more casual feel on the body.”
“London tailors of Savile Row because of their commitment to tradition and precision, and Scandinavians because their lifestyle dictates their fashion. Also: Bond.”
“Spectacle. I love my shades—you can feel like a totally different person in glasses.”
Garrison Bespoke flannel suit, poplin shirt, pocket square and brogues; Fumagalli paisley tie.
The 40-year-old owner of the Jordan Group of Companies (a partner in lookbooks.com) splits her time between Rosedale and Chelsea, New York.
“Mix of everything new and vintage.”
“Hold on to special pieces. Fashion always comes back around.”
“The designers Azzedine Alaïa, Brian Atwood and Adam Lippes for their incredible taste.”
“White tank tops from the Gap, which I pair with designer pieces by Givenchy and Christopher Kane.”
“Diana Ross in Mahogany and the conceptual artist James Turrell for his fantastic perspective.”
“Pony-hair shoes by Brian Atwood.”
“L’Atelier for home, The Room for everything pretty and Teatro Verde for beautiful flowers and gifts.”
YSL dress, Tom Ford gladiator boots, Lanvin belt, Bottega Veneta fingerless gloves.
JT: The 27-year-old is an elementary school teacher at Howlett Academy.
DT: The 34-year-old is the founder and designer of the label 18 Waits.
JT: “Mainly boho, sometimes rocker.”
DT: “Elegantly dishevelled.”
JT: “Edit your closet every season and, as my husband, Daniel, says, make friends with a good tailor.”
DT: “It’s an ongoing obsession: the Rolling Stones and their style in the 1970s.”
JT: “The Parisian lifestyle, the Little Golden Books from the 1970s and my parents’ old photo albums from when they lived in Poland.”
DT: “Workwear from the past, including fishermen’s clothes, plus the Wild West and gypsies.”
JT: “A cozy wrap-around vintage scarf.”
Vintage blazer and hat, Urban Outfitters jumpsuit, Jenny Bird canteen purse, Ka’kia necklace.
18 Waits clothing and jewellery, Lunettes Kollektion glasses, scarf from a fabric store in Paris.
She’s 33 and the director of brand strategy at Holt Renfrew.
“I love adding a unique element—something with a story—to a classic look.”
“Aish scarves and jewellery, Lizzie Fortunato accessories, Kenzo pants, Helmut Lang blazers.”
“A great blazer, simple pumps and a cool accessory. I’m a working mom, and these three items transition my outfit from early morning soccer to office chic.”
“Stella McCartney, who stays relevant while never compromising her commitment to social awareness. Livia Firth’s work on the Green Carpet Challenge, a partnership with top designers using sustainable products.”
Burberry Prorsum skirt, Dries Van Noten top, Lizzie Fortunato clutch, Aish jewellery.
The 30-year-old is the owner of the Queen West accessories shop Zane.
“Polished, relaxed, cool.”
“Kenzo’s fun prints and colours and Yves Saint Laurent’s clean lines.”
“Black leather jackets.”
“My friend Jamie Webster, a director at the fashion collective Common Good. I respect his work as an artist and his cutting-edge ideas. Also, New York and Paris.”
“A Sheffield watch by Daniel Wellington—it doesn’t have a second hand, so I won’t feel rushed—and a classic, hand-painted Il Bussetto wallet.”
Sandro jacket, Oak and Fort cardigan and pants, Kin dress shirt, Etiquette socks, Hugo Boss shoes.
The 36-year-old Bird is creative director of her eponymous accessories label.
“Mara Hoffman’s new prints for fall-winter 2013. And Lucite, in everything from fashion to furniture.”
“Maxi dresses and printed pants.”
“My mom, Linda Bird. Dressing is one of her great pleasures, and she transferred this joy to me. Designers Ossie Clark and Celia Birtwell, print designer Florence Broadhurst and style icons Grace Coddington and Talitha Getty. They all have a bohemian-meets-uptown style.”
“Rag and Bone knits and boots. Sass and Bide anything.”
Raquel Allegra dress, Theyskens Theory cape, Nine by Four hat, Jenny Bird jewellery.
Brown, who’s 27, is the creative director at the vintage collective The Art of Reuse.
“Eddie Vedder graduates from Princeton and forms a jazz band.”
“You dress better when your room is clean.”
“Diptyque candles burning in an all-white space with Future’s ‘Neva End’ on repeat.”
“Abused off-white Chuck Taylors.”
“Eddie Vedder, Grace Coddington and the designer Richard Chai. These people brought a sense of the inner city to music and fashion. Also, the film Rockers from 1978 embodies the type of clothing I want to design, with a modern approach.”
“A varsity jacket by Needs/Wants Studios, a brand I conceived earlier this year. #shamelesspromotion”
“Purple acid-wash pants from American Apparel in 2007. Luckily, no pictures were taken and I recovered gracefully.”
New Balance T-shirt, Needs/Wants peacoat, Acne sweatpants, American Apparel socks, Adidas sneakers.
The former ad executive publishes the apps WearToday, Dogbook and Catbook. He’s 60—“but just,” he says.
“As joyful as possible.”
“Colour brightens not just your day but others’ too. And layer—it’s a long winter.”
“I admire Philip Sparks, I follow artcomesfirst.com—a couple of truly amazing gentlemen from the U.K. who inspire me daily—and I’m very fond of using the Paper app on my iPad.”
“Mixing high with low—white Gap jeans with a Loro Piana jacket and a vintage scarf, for instance.”
“My father, Robert, wasn’t fancy but he wore clothes very well. My eldest son, Alexandre—I’m jealous of his sense of colour and pattern and how well he puts things together.”
“A salmon-coloured raw silk suit I bought in 1975. I was beaten up shortly after in a disco.”
Stenstrom shirt, Levi’s jean jacket, Brunello Cucinelli quilted jacket, Grown and Sewn pants, Etro scarf, Geier gloves, Tom Ford shoes with Stolen Riches custom laces, Opticianado glasses.
The 30-something freelance stylist and creative director spends most of her time in Toronto, New York and L.A. on work assignments.
“Confidence is the first step to good style.”
“Like so many others, I’m obsessed with Phoebe Philo at Céline. Besides changing the direction of fashion a few years ago, she has an authentic aesthetic and approach. It’s never trying too hard to be ‘fashion.’”
“A black Chanel blazer.”
“I’ve been fortunate to see a lot of the world, from Berber villages in Morocco’s countryside to sensory overload in Tokyo. People, nature and food provide endless inspiration and creative rejuvenation.”
“The entire Givenchy collection is jaw-droppingly gorgeous.”
Comme des Garçons top and skirt, Chanel blazer, Alaïa boots.
The 42-year-old is a baseball analyst on Sportsnet.
“I dress myself like an interior designer would decorate a room: matching colours, with lots of patterns and texture.”
“Don’t be afraid to take chances. It’s only one day of looking bad if it goes awry.”
“I love cufflinks, pocket silks, the double-breasted suits by my designer, Antonio Valente, and Mezlan exotic-skin shoes.”
“Crocodile shoes in as many colours as I can get them in.”
“Don Cherry and Denny Crane [William Shatner’s character on Boston Legal]. My stylist Deb Berman helps me achieve my look.”
“Every Canada Day.”
Antonio Valente suit, Dion Collection tie, Rolex Daytona watch, Barclay Jewellers amethyst cufflinks, Persol glasses, his 1997 World Series ring.
DR: The 21-year-old co-owner of the fashion website and accessories line Kastor and Pollux lives in Scarborough.
BV: Roche’s partner in Kastor and Pollux is also 21 and lives in Scarborough.
BV: “Mixing different influences with a smidge too much quirk.”
DR: “Impractical platform shoes and bags big enough to fit my MacBook.”
BV: “Anything yellow.”
DR: “The designers of Rodarte for prioritizing artful qualities over practicality. I like collections that are visually stimulating and have stories behind them. And the print mastery of Dries Van Noten.”
BV: “Fashion icons Michelle Harper and Miroslava Duma. I have a semi-creepy folder saved on my desktop filled with images of these two.”
DR: American Apparel long-sleeved top, Silence and Noise strapless top, Chloé boots, vintage Escada skirt, Kastor and Pollux necklace.
BV: Forever 21 sweater, vintage beaded cardigan, Asos harem pants, Jeffrey Campbell heels, J.Crew earrings.
The 40-something president and head designer of Pink Tartan lives in Forest Hill.
“I like sophisticated and elegant clothes with a sense of humour and details that are thoughtful—a raw edge, a special button, an interesting seamplacement.”
“Homemade hot-air popcorn—my favourite snack—sprinkled with Maldon salt from Williams-Sonoma and a drizzle of olive oil. And my husband, Joe, and I have just finished building a beach house:I admire a minimal, precise space filled with modern art.”
“I adore the taste level of Diana Vreeland, Audrey Hepburn, Coco Chanel, Yves Saint Laurent, Christian Dior, Hubert de Givenchy and Cristobal Balenciaga—not only for the fashion they wore or designed, but also their exquisite living spaces.”
“I’m loving a longer skirt length, either full or pencil, and a moody floral print.”
“I Miss You on Ossington for vintage pieces.”
“I have been known to put my clothes on inside out—always rushing!”
Rochas dress, Céline clutch, Seaman Schepps bracelet, Dior heels.
She’s 25 and works at Holt Renfrew as a co-ordinator of fashion direction.
“Like Gwen Stefani said, it’s ‘style detached from content, with a fatal attraction to cuteness.’”
“Next time you see something and think, ‘It’s not me,’ try it on anyway.”
“Vibrant Japanese culture and fashion, which I find fascinating. I’m planning a trip there for 2014.”
“Every girl needs a pair of Manolo Blahnik BB pointed-toe pumps.”
“I have a crush on Anne-Catherine Frey; she’s a designer and blogger living in Paris and I want to be her friend. Also, New York casting director Natalie Joos’ effervescent style and the art of Yayoi Kusama.”
“A statement coat, a simple backpack and a menswear-inspired loafer.”
Carven patterned top and heart-shaped collar, The Row leather pants, Yves Saint Laurent bag, Jenny Bird bangle, Valentino shoes.
The 39-year-old former Little Mosque on the Prairie actor lives in King West.
“Gore Vidal said it best. ‘Style is knowing who you are, what you want to say, and not giving a damn.’”
“The KISS principle—keep it simple, stupid.”
“I always wear a jacket, whether it’s a blazer or a bomber.”
“The Rat Pack with a soupçon of Brando, Dean and Clift. Also, I grew up in a home where we watched Fashion File and FT. Throw in the Beatles, Stones, Elvis and Neil Diamond with some Bollywood singers, and you can’t help but be inspired in many ways.”
Zegna leather jacket and Ron White ankle boots.
Ben Sherman T-shirt, Zegna jeans, Burberry sweater and trench, David Yurman watch.