The Best Dressed List

The platinum drag queen became Canada’s newest national treasure the moment she stepped into the Werkroom on RuPaul’s Drag Race and crowned herself Queen of the North. As the only Canadian on an American show, Hytes donned a Mountie uniform bedazzled in maple leaf–red sequins, fulfilling the collective camp-glamour fantasies of a country. And she has the selfie to prove it: there she is on Justin Trudeau’s Instagram feed, the prime ministerial arm wrapped around her six-foot-seven (in heels) frame, posed like an otherworldly goddess and draped for Pride in ultramarine. Brock Hayhoe, the Etobicoke man behind the queen, imagined BLH as a wealthy and powerful Amazonian, a style child of Linda Evangelista and Grace Jones, all extreme cheekbones, shiny vinyls, space-age silhouettes and, as he puts it, “bitchy shoulders,” softened by Hayhoe’s balletic aura (earned through years of classical dance training). Hytes finished second in her season of Drag Race, but racked up almost a million Instagram followers and a gaggle of endorsement deals in the process, making her Toronto’s most influential and beloved lewk queen. Read the Toronto Life profile of BLH here.

The Toronto Raptors power forward had a very good year between all those opponent-crushing blocks and the whole championship thing. But it was his pre-game walks down the media tunnel at Scotiabank Arena that turned him into an off-court style sensation. Slick, custom-made suits, bold colour pairings and hats aplenty—cashmere beanies and leather ball caps, polished newsboys and one memorable cherry-blossom-pink fedora—earned him a Vogue stamp of approval and front-row seats at men’s fashion weeks all over Europe. He flitted from show to show in designer pieces, each better than the last: a knee-length lily-of-the-valley-printed coat at Valentino, an outsized Balmain poncho emblazoned with a desertscape awash in golden-hour tones, and a Thom Browne kilted skirt suit worn without a lick of irony or insecurity.

Born and raised in Iran, Dorian Rahimzadeh was a reluctant adherent to her country’s modest dress code, longing to play with nail polish or wear a simple pair of sneakers, both verboten there. At 22, she attended fashion school at LaSalle College in Istanbul and soon made her way to Toronto, a move she describes as “an explosion in my mind.” Now she’s the creative director behind her own avant-garde line, Dorian Who, where she experiments with a playful more-is-more ethos: shorts and pants ballooned to cartoonish proportions, sleeves so puffed they’d dwarf Lady Di’s on her wedding day and hats with just a dash of Fraggle Rock eccentricity.

The Toronto-born model’s rise through the fashion ranks has been slow and steady—a turn on America’s Next Top Model, a cameo in Beyoncé’s visual album Lemonade, a Sprite ad—until this year, when she pulled off the model’s equivalent of a hat trick: a Vogue cover and a coveted spot in the annual Victoria’s Secret wings-and-G-strings extravaganza. And with supermodeldom comes red carpets. Harlow worked for four months on her Met Gala look with fashion fairy godfather Tommy Hilfiger, who designed a beaded bra and skirt inspired by Harlow’s Caribbean roots and, daringly, the movie Showgirls. She also fearlessly worked the Cannes film festival, first in a red tulle ruffle dress and matching veil by Jean Paul Gaultier, then in a sheer Ralph and Russo number that wrapped a faux crocodile around her lithe torso. Rumour has it she’s about to break into the beauty biz, too, with an upcoming kollaboration for Kim Kardashian’s KKW line.

The gossip blogger, co-host of The Social and eTalk presenter would rather be polarizing than pretty, goofy than boring, brazenly pig-tailed than sleekly low-ponied. Her no-basics-allowed spirit comes from a girlhood spent idolizing edgy pop icons like Janet Jackson, Madonna and Lisa Lisa and, at age 45, knowing exactly what works for her—and how to ask for it. “When I first got into TV, the bandage dress was really in,” says Lui. “So I did the bandage dress—I didn’t have a style voice to be able to speak up and say, ‘Bodycon isn’t my thing.’ Over time, I grew as a person and became more assertive. Thankfully, we’ve since imagined other ways for women to look. On-trend clothing doesn’t have to be tight; it can be dimensional and asymmetrical and baggy and boxy.” Baggy and Boxy could easily be the name of a Lainey Lui workwear line designed for the woman who dashes from TV set to laptop (where she pumps out up to 4,000 words a day). “I have very little free time to fuck around. Clothes that restrict me also restrict my productivity,” she says, explaining a commitment to comfort so radical she hasn’t worn an underwire bra in nearly seven years.

The Toronto-born Brother Vellies designer is best known for her elegant sandals, slides and pumps handcrafted in Kenya, Ethiopia and South Africa. They’ve graced the famous feet of Rihanna and Solange and recently earned her CAFA’s international Canadian designer award, an accolade bestowed upon heavy hitters like Erdem Moralioğlu and Jason Wu. This year, her personal style, from the ankles up, also had fashion insiders buzzing. James rolled into the Girlboss conference in a sweet puffed-sleeved babydoll blouse paired unexpectedly with a set of knee-length bicycle shorts and a froth of natural curls. And for the 2019 Met Gala, James had Brother Vellies artisans create several custom pieces, including three dresses woven with bamboo, wood, raffia and feathers—an earthy, African-inspired counterpoint to camp’s technicolour plasticity. She ended the Gala night in a halo of monarch butterflies perched, mid-flutter, atop a cascade of braids.

As a fashion creative, Poole spent years in New York City’s style pressure cooker, first at Barneys and then at V Magazine, where she conformed to a buttoned-down, upper-east-side look predicated on Céline bags and look-at-me labels. But it never felt like her. “I’ve worked in many environments where I was the only person of colour, so the need to assimilate was very strong,” she says. “But of course, this desire to blend in conflicts with a larger wish to feel free and be myself.” Now back in her hometown and installed as the VP and creative director at the chic-and-chong cannabiz Tokyo Smoke, she dresses more casually and expressively, which means bodysuits with blazers, work-appropriate tie-dye and denim with a twist: “I love my pair of Y/Project jeans. They’re super weird, structured and bizarre. They’re a conversation,” says Poole.

The 21-year-old human sunshine emoji got his big break last January when he posted an Instagram video of himself dancing in his parents’ Scarborough basement, all Beyoncé booty and life-affirming swag: “Keep on working your dream,” “You can do anything.” Queen B herself shared the vid, Ariana Grande invited Colley to dance in her “Monopoly” video and he garnered 784,000 followers, who now take style notes from their favourite motivational meme maker. Colley’s look is an idiosyncratic blend of adorable new adult (overalls), Canadian practicality (over 50 toques in bright, mood-lifting colours for grey Toronto winters) and gender-fluid fun (wide-legged, high-waisted pants). “Growing up with a single parent,” says Colley, “I’d look at my mom and wonder why there weren’t any guy’s styles like that. I’d go to the women’s section to see what I could find, because fashion is about not giving a shit.”

The Toronto-based Egyptian artist has gained international acclaim for her thought-provoking installations and still-life paintings that take on identity and immigration. When it comes to dressing, her style sense is as surprising and fresh as her work. Take, for example, the time-tested concept of a statement piece: “I don’t like to have just one loud thing,” says Gohar. “If you’re going to do a statement, you have to add in another statement so it’s not standing on its own. Have a few statements and then you can add a basic.” She layers those sartorial assertions like a well-crafted contradiction. See: a cream puff Simone Rocha blouse on top of a military-grade canvas kilt, heavy with hardware and masculine pleating. But most of her days are spent more casually dressed in a studio uniform of jeans or classic black pants and sweaters covered in paint, plaster and woodworking dust. “I don’t feel too precious about anything,” says Gohar. “I’ll wear something to the max and then if it’s done, it’s done.”

This summer, O’Hara received an Emmy nomination for her portrayal of clothes horse gadabout Moira Rose. The character’s evolution from self-involved soap star to self-involved resident of nowhere Ontario has brought five seasons of outfits so outrageously unfit for small-town life that Schitt’s Creek’s costume designer, Debra Hanson, was nominated for an Emmy of her own. O’Hara has been an essential part of creating Moira’s look from day one, bringing to early show meetings a mood board that included the avant-garde English socialite Daphne Guinness. That offbeat inspiration translates into to a dressing room stacked with labels (Alexander McQueen, Isabel Marant, Balenciaga and Givenchy), brooch-bedazzled sleepwear (Moira likes to keep her pajayjays formal), and wigs to suit her many moods (our favourites: punk Queen Elizabeth and goth Goldilocks). Ever the actor in search of subtext, O’Hara has described her character’s use of fashion as armour, protecting her as her big-city life is ripped out from under her. If that’s the case, Moira Rose is having the chicest identity crisis on TV.

For the Heartbreaker novelist and co-owner of the cult fashion line Horses Atelier, dressing is a daily act of authenticity. “From the earliest age, I saw style as an expression of personal liberty and self-respect,” she says. “It was a feminist act, a form of autobiography. A woman must dress for who she is inside at that moment.” Naturally, Dey has always skipped the mall in favour of her mother’s closet, costume trunks and vintage stores, where she hunts for timeless treasures, like her grandfather’s blue velvet tuxedo jacket, a pre-loved tourist T-shirt, a ladylike pair of high-heeled boots and Victoriana of all kinds. The result is a well-lived-in sartorial spirit that flickers teenage angst one second—jeans, combat boots and outsized fisherman knit—and flashes midlife empowerment the next: “My hair is turning silver and this feels like a small mercy. I can’t wait to turn 50,” says Dey.

The dapper Scarborough-raised actor is the biggest thing to graduate from the halls of Degrassi High since Drake. This past year, he starred in two knockout productions, the Oscar-nominated If Beale Street Could Talk and the eminently creepy speculative fiction series Homecoming, alongside Julia Roberts. When his big break came, James was ready to dress the part in a lineup of impeccably tailored suits that telegraphed quiet luxury with a twist. See: the green velvet Burberry number he paired with high-heeled floral Christian Louboutin Chelsea boots, or a berry Etro tux studded with a starburst lapel pin and contrasted with gleaming white boots. But only close observers will notice his most surprising accessory of all: a dainty nose stud that’s barely perceptible in photos—and a dead giveaway that James is a child of the ’90s.

The Toronto-born photographer, curator and videographer spent 2019 upholding her status as an alternative it girl and millennial emissary for Gucci, infusing her looks for the label with a wilted-flower Virgin Suicides aesthetic that dominates the rest of her portfolio. Her #currentmood was best expressed at this year’s Met Gala, where she donned three mod looks. First, she was a vision in ornate ’80s-inspired chintz, complete with puffed sleeves, a bubble skirt and an artfully exposed midriff. Next came a shiny black latex bodysuit under a ruffled strawberry-print jumper by Alessandro Michele for Gucci. And later, she lit up the floor at Gucci’s high-school-dance-themed after-party in a tiered and fringed turquoise gown reminiscent of an under-the-sea prom. Collins’s boldest style moment of the year, however, happened when muse turned artist: for her collaboration with the erotic publication Baron Magazine, Collins cast mannequins from her own body and dressed them in ethereally feminine looks rooted in childhood memories, which means Laura Ashley leotards, ruffled ankle socks and bright white bralette-and-panty sets.

The classically trained tenor, Polaris winner and Indigenous rights activist sees his personal style as a form of political expression. Take the astonishing custom cape he wore to the Junos this past winter. A gauzy butterfly garden twirled and trailed around his body, symbolizing the current blooming of Indigenous artists; underneath the cape, printed in Cree characters, was the phrase “We Will Succeed.” On daily dressing, Dutcher, who is two-spirited, says, “It’s never male at one end of the spectrum and female at the other—it’s more of a circle. Almost all the rules around fashion are methods of control, and I don’t buy into any of that. The whole point of fashion is freedom.”

The city’s splashiest socialite has a jam-packed social calendar: co-chairing several fundraising galas, sitting front row at Dolce and Gabbana’s couture show and mingling with fashion’s upper echelon, including Gucci creative director Alessandro Michele and model Coco Rocha. All that hobnobbing requires a deep closet of runway gowns and sky-high heels. Her look—decadent on an ordinary day—has soared to even more extravagant heights this year. She spent three months working with Canadian designer Stephan Caras on a custom CAFA dress dripping in lace floral appliqués and 3,000 hand-sewn Swarovski crystals. And on her annual pilgrimage to Dolce and Gabbana’s Alta Moda presentation, she went full fairy-tale, donning a street-clearing ball gown with a cornucopia-inspired print and off-the-shoulder Victorian sleeves, topped off with a regal golden crown. The effect was so compelling that a gaggle of Italian choir children embraced her like a real-life Disney princess.

David Zilber grew up making matzo balls with his mom in Scarborough, a self-dubbed dorky kid in sweatpants and Birkenstocks. Now a culinary polymath manning Noma’s fermentation laboratory in Copenhagen, Zilber has honed a fashion sense that’s as bold and playful as his kitchen experiments. “I’m unapologetic. I’m not afraid to be noticed. I dress very brightly, but there’s not so much going on that you’re blinded and confused by straps and dongles,” says Zilber. Those pops of pantone are a happy hangover from his days of dancing to electro-disco in the mid-oughts, and his signature aviators come courtesy of his father, who wore the same model long before Kim Kardashian made them a thing. “I might come to work in Comme des Garçons pants,” says Zilber, explaining his always-on approach to dressing, “and I might only be wearing them for an hour that day, going to work and back, but I’d rather be on my A game.”

The go-to photographers for OVO and the sharpshooting couple behind Drake’s iconic Scorpion album cover, Wong and Schill have cultivated a joint image of cool minimalism: black on black on black for Wong and fresh whites, creams and beiges for Schill. For two-year-old Lius, they splash out on kicks—“He has quite the sneaker collection for his age. He chooses the shoes he wants to wear each day,” says Schill—and dig up adorable vintage mementos. “We recently found some of my childhood clothes from Germany in a box, she says, “so Lius has been wearing a lot of vintage, like a super-old U.S. military jacket my grandfather got from a surplus store in a baby size.”

The model, former Glamour editor and founder of Henning, a workwear label for women sizes 12 and up, learned about fashion the way most teens did not so long ago: through print magazines. She had a stack of them in her Brantford, bedroom, the most coveted title being Vogue. That’s where she learned to think about editorial presentation of fashion. But she didn’t see her body represented in those pages. “I’ve worn sizes from 12 to 20,” she says, “and when you don’t see yourself, it’s hard to imagine putting those clothes on.” Instead, the plus-size section offered her garish floral patterns and muumuus. Now that she runs her own brand in New York City, she’s continually inspired by the city’s multiplicity. “The amazing thing about living here,” says Chan, “is that there are so many kinds of people. I look to the women around me every day—whether I work with them or see them on the subway.” She dresses for ping-ponging between meetings, errands and dinners: a roomy APC tote that fits business-ready heels and an umbrella, jeans, soft button-downs, tailored blazers and not a tropical muumuu in sight.

Holt Renfrew’s VP of accessories grew up wanting to be an Olympic skier, coveting the highest-tech gear every season. As an adult with two business degrees, that near-nerdy enthusiasm for the latest and greatest goods has translated into a plum fashion job and a closet full of finds plucked, often months before they hit boutique shelves, from her many buying trips to Paris and New York City. Keepsake items, like elegantly elfin heels from Phoebe Philo’s last Céline collection, or custom black diamond eternity bands set by Spinelli Kilcollin, add special-occasion awe to a sturdy set of staples that, as Wright describes them, skew masculine and practical, never frilly. That means wide-leg black trousers, pleated skirts and long, well-cut coats. “There’s nothing better than an oversized white shirt,” Wright says with the fuss-free minimalism reserved for the truly fashion-fluent.

After a mental health break from social media last fall, the Scarborough-raised YouTuber with 15 million subscribers is bigger than ever. This month, she’ll take over Carson Daly’s 1:35 a.m. slot as host of A Little Late With Lilly Singh, becoming a unicorn on the late-night scene: a queer woman of colour under the age of 40. As her star has risen, Singh has refined her sporty, live-from-her-bedroom look. She still wears her cherished baseball hats, sneakers, baggy jeans and bra tops (all in top form courtside during the Raptors playoff run), but has also proven she can sparkle with the brightest red-carpet stars of her adopted home, Los Angeles. See: the disco ball of a body suit she wore to the Grammys, or the chartreuse layer cake of a Christian Siriano gown she strutted at the GLAAD awards. And for her turn as the millennial Johnny Carson, expect plenty of power suits, which she wears in a rainbow of mood-brightening hues, all accessorized, of course, with her bawse attitude.

As a designer, artistic director of Indigenous Fashion Week Toronto and costumier (she’s created looks for Kent Monkman’s fabulously gender-fluid alter ego, Miss Eagle Testickle), Paul is keenly thoughtful about her style. “I struggle with having a professional persona,” she says. “I don’t want to seem inaccessible to emerging designers or Indigenous designers. If I’m in a dress or wearing a blazer, I like to dress things down, so I typically wear sneakers or flat shoes—sometimes Doc Martens or Vans.” Those last accessories, like other pieces in her closet, are a nod to her upbringing in the grunge-loving 1990s, when she took notes from the Cranberries, Garbage and No Doubt, not to mention her father, who would hand her down his flannel shirts and denim jackets. She’s also conscious of the impact fashion has on the planet and weaves together her wardrobe from Value Village finds, upcycled textiles and DIY garments. “I don’t want to hurt the Earth more, and that’s an important part of Indigenous culture,” says Paul. “When you hunt an animal, you use every single piece of it, for clothes, food and tools.”

Once an adolescent pop punk outfit, the Toronto quad have arrived as chic alternative rockers—so talented the Rolling Stones tapped them to open a concert this past summer. On stage, the women are a high-energy blur of feathers (Jordan’s vintage Motown gown), fringe (Leandra’s western leather jackets), silver (Kylie’s fistfuls of rings) and red lipstick (Eliza won’t go onstage without it). “Embracing our femininity is really important to us as rock musicians but also as young women,” says Jordan. “You can hear that in our music, too. The base is rock but all our lyrics are about being young women in Toronto.” True to that vision, their collective style influences are diverse, clashing and playful. There’s Alice Cooper, Edie Sedgwick, David Bowie and Shania Twain. (On Shania, Kylie says, “I wore a denim shirt with denim jeans with a star on the butt. I ripped them on the dance floor. I dropped it too low and they split down the ass. It was tragic.”) The resulting glam-girl vibe is an impressive evolution from the band’s early look, when Leandra once showed up for a gig in a hockey jersey: “I was like, ‘The Leafs are playing tonight, guys!’”

If you ask mother-and-daughter Sue and Tanner Kidd, an arts patron and interior designer, respectively, to describe the other’s personal taste, each will de facto describe her own: “My mom’s style is elegant and classic, with a contemporary twist,” says Tanner. “Tanner is classic,” says Sue, “but there’s always an element of fun.” The two even wear the same scent: Jour d’Hermès. Their highly polished mirroring is perhaps what happens when a strong sense self-possession is passed down through generations of women, manifesting a little differently as the decades pass. “Both my grandmothers liked to dress nicely,” says Sue. “And my mother was a stay-at-home mom, but she always changed into a nice pair of slacks and a sweater when my dad came home for dinner.” Tanner drew the same lesson from Sue: “I always remember my mom coming to pick us up from school and people would say, ‘Your mom is such an elegant woman.’ That’s the biggest thing I’ve tried to pull into my everyday style: it’s important to make an effort. I think people feel a level of respect for that.”

With a world tour, two Grammy nominations and a Calvin Klein underwear campaign, the formerly awkward teenage Vine star (turned preposterously chiselled Billboard chart topper) is officially one of music’s major players. Mendes’s longtime stylist Tiffany Briseno recently told Vogue that his look can be broken down into three stages: during the “plaid stage” he wore whatever he wanted; the leather jacket stage was an attempt to skew a little more mature; and now, for his latest world tour, they worked together on a stage they call “natural rock star,” a mix of custom designer pieces (Calvin Klein, Dzojchen, Dsquared2, Saint Laurent) and vintage finds. This stage, it seems, is inspired by a pantheon of rock gods, including Elvis (the collared shirts), Jimi Hendrix (the prints), James Dean (the hair) and Bruce Springsteen (the jean vests). Or maybe every character in The Outsiders. The general rule is to layer up at the beginning of a concert and slowly disrobe—à la James Brown—as the show goes on. Briseno said that the idea is to create a sense of anticipation throughout the show, as the layers come off. Mission accomplished.

Not long ago, Mulroney was best known as Ben’s wife or Meghan Markle’s BFF and (unofficial) stylist. After the royal wedding and her viral butt moment, however, the socialite has become a superstar in her own right, landing a gig as Good Morning America’s style guru. Though she’s breaking big stateside, Mulroney is often called the fairy godmother of Canadian fashion for her commitment to northern designers. At this spring’s CAFAs, she wore a champagne-coloured bodycon gown by Montreal designer Caroline Constas; her polished power suits often emerge from the studio of Toronto blazer savants Smythe Les Vestes; and she’s a devotee of Nonie, the Calgary label responsible for the ankle-skimming leopard-print coat she wore in a recent Harper’s Bazaar photo spread. So if you’ve seen more celebrities in Canadian labels lately, Mulroney likely has something to do with it. Rumour has it she’s even convinced Mindy Kaling, one of her other unofficial celebrity muses (she says her influence on her famous friends is more organic than a stylist-client relationship) to don a Rosedale-ready suit by the Montreal label Landscape Clothing. Proof that Mulroney’s fashion influence goes way beyond Instagram.