At Toronto shop Labour of Love, owner Regina Sheung curates a thoughtful selection of giftables such as paper goods, apothecary items and handmade jewellery. It’s a cheerful retail approach that the 48-year-old spreads over to her colourful ensembles, a sensibility that she attributes to her haircut. “My current sense of style was greatly influenced by my hair stylist,” Sheung explains. “She gave me my first pixie cut, which inspired a more playful energy.” In Sheung’s wardrobe, that energy manifests itself via creative combinations such as a linen wrap dress by Cedar & Vine that Sheung wears as a vest over a denim jumper by Ilana Kohn, or a wool dress by Kloke under a boxy coat by Pas de Calais. “I’m an emotional dresser and use clothing to express myself. It’s a great conversation starter and an easy way to communicate who I am,” Sheung says. To get the message across, Sheung sets aside a few minutes every Sunday to plan her outfits for the entire week, selecting core pieces and layering on accessories the day of, saving her most flamboyant add-ons for the weekend. “I work Saturdays and so my wardrobe is less focused on comfort and more on style, energy and fun. This way I’m ready for any social events right from work.”

An individual sense of style is something that Toronto-based hairstylist Sergio Rodriguez developed out of necessity at a young age. “I quickly learned the hard way that, to other kids my age, being a twin wasn’t cute or cool,” he says, explaining that he and his brother, who were born in Argentina, would take turns adopting the look of a different subculture as a way to differentiate themselves. “When I was a goth, he was a hippie. When I was a rockabilly, he was a mod.” Now 42, Rodriguez constructs his outfits around two different facts of life: first, his destination, and second, how he’s going to get there. “Where I’m heading will always define my sense of style,” he says. “If I’m driving or riding, I will most likely wear something to accommodate and complement the vehicle I’m in,” he admits. With options that include his two vintage cars, a motorcycle, bicycle, public transit or on foot, it’s easy to see why co-ordination gets top priority. While some of his staple day-to-day pieces are by Britain’s Fred Perry and Japan’s Black Sign, he reserves his favourites – including custom designs made by his wife, Tara Kelly – for special occasions. “I don’t enjoy having my good clothes covered in hair.”

“I am comfortable in my own skin. While I may be inspired by trends, they do not dictate what I wear,” says Gurpreet Kaur Ahluwalia, a marketing consultant with a fashion background. Her work life and philanthropic pursuits have led to many nights on the town, where a special-occasion ensemble could include a piece from Indian designer Anamika Khanna or Italian house Brunello Cucinelli. “My siblings were huge inspirations growing up,” she says. “They range from 10, seven and five years older than me, and I always found myself taking fashion risks because of them. The lesson that style should be timeless came from my eldest sister, Sukhbir.” Now Ahluwalia has carved her own niche in the Toronto fashion industry, punctuated by wearing more classical items such as blazers and trousers done in unusual silhouettes and patterns; she notes that her downtime is when she’ll “often try some of my more avant-garde looks, to see if I can pull them off at work or an event.” When it comes to her style direction, Ahluwalia highlights four key elements: “Oversized because I always crave comfort, structured because I like to borrow elements from men’s fashion, conservative because I love crewnecks and my collarbones rarely see the light of day and fun because I like to take risks.”

“First and foremost, my personality is pretty transparent to everyone I get an opportunity to interact with,” says Isaac Mbaziira, a print-loving relationship manager at Chartered Professional Accountants of Ontario. “This allows me to express myself in a way that is pretty much already expected.” Those in corporate roles often relish doing downtime dressing differently from their day-to-day, yet Mbaziira – who favours the quirky shoes of Canadian designer John Fluevog and high-street hip of Topman when it comes to his wardrobe essentials – says he’s been able to tread the line between official and outrageous regardless of his surroundings. “I found a way to combine both styles and make them work within the same environment, so that I am able to still retain my sense of self-expression.” Mbaziira credits his parents for influencing his eclectic sartorial sensibility, noting his mother would encourage him to flip through kid’s boutiques’ catalogues to get a sense of his own style predilections at a young age. “Being born and raised in Uganda, my parents have always been attracted to colourful outfits and that rubbed off on me as I grew up,” he says. These days, Mbaziira looks to the likes of multihyphenate Pharrell Williams and actor Chadwick Boseman for inspiration, and you can see hints of their unique styles in his own novel ensembles.

For Johanne Durocher, a life lived artfully involves everything from her soundtrack of choice (jazz) to her after-work tipple (tiki-inspired cocktails) and, of course, her clothing. “I feel that I get the most out of life through a myriad of small, enhanced moments throughout the day and what I wear is part of that way of living,” says Durocher, who was born in Thetford Mines, Que. Durocher’s strong love of vintage clothing has resulted in a closet filled with one-of-a-kind treasures that lend her an unmistakable look: loungewear by Christian Dior, silk pants from the 1940s and an exquisite collection of headwraps and chapeaux. “I always travel with a hat,” she says. The 40-year-old, who works in strategic communications at CBC/Radio-Canada in Toronto, says that, for her, it’s difficult not to come across as distinctive in her way of dressing. “Sometimes I’ll have a day when I’m heading out and I want to blend in with everyone else, but it’s a challenge and it always ends up feeling like a pep talk with myself,” she says. On festive occasions such as a concert or museum opening party, Durocher goes full glam in statement pieces such as a gold jumpsuit made for her by Canadian designer Evan Biddell or a brocade playsuit and matching sheer skirt from the 1960s. “People might be comfortable wearing jeans,” she says. “I feel comfortable in my psychedelic pants.”

To succeed as a social columnist, going from ballroom to boardroom and everywhere in between, one must possess a chameleon-like ability to blend in while standing out. It’s a savvy sartorial skill that Vancouver’s Fred Lee has in spades. “With my suits, they generally go from day to evening quite well,” the 52-year-old explains of his collection that includes names such as Hugo Boss, Calvin Klein and Emporio Armani. The director of alumni engagement at the University of British Columbia, in the evenings Lee hits the city’s party circuit, chronicling the comings and goings of Vancouver’s social set on CBC Radio’s The Early Edition and in columns in The Province, Vancouver Magazine and Vancouver Living Magazine. He also takes on hosting duties at charity events for organizations such as CampOut, a summer leadership camp for LGBTQ youth and their allies. With such a full social calendar, Lee turns to playful accessories to keep his look fresh, embellishing his signature suits with pocket squares, cufflinks, watches and tie clips. But there’s one staple he’s been wearing nearly every day for years: black patent shoes. “They have always made a positive impression, whether with my jeans or my suits,” he says. “They really elevate an outfit, in my books.”

“Clean” is a theme throughout Mary Futher’s life. As the founder of eco-beauty brand Kaia Naturals, Futher works to redefine Canada’s skin-care choices; she also favours simplicity when it comes to her own wardrobe – the quick addition of combat boots takes her outfits from polished to playful. Describing her look as “timeless with a dark twist,” Futher sticks to a black palette using pops of colour sparingly – “mostly kept for my lips,” she says. Relying on the appeal of black’s chic mysteriousness, it’s no surprise that Inès de La Fressange, the French fashion muse, is one of her icons, as is Linda Rodin, the skin-care entrepreneur and former model whose hallmark style includes a pair of eye-catching glasses; Futher’s own bold black frames have become a signature of sorts for her as well. Their commanding presence plays off structured garments from COS and Canadian fashion icon Lida Baday – Futher’s go-to brands – with fabulous finds from designer resale shops such as Rewind Couture taking residence in her closet, too. Futher also indulges in the occasional trip to New York’s Century 21 store, noting that “you never know what you are going to find!” While she considers her all-black-everything look a uniform, there’s certainly nothing standard about it.

For a fashionista with a cultured eye, working at the George C boutique in Toronto’s tony Yorkville neighbourhood has more benefits than proximity to stylish apparel. It’s also a natural starting point for exploring the city’s most inspired locales. “I spend a lot of time finding conceptual spaces, whether it’s shops, art galleries or somewhere to grab a drink,” Maxwell Graydon Thompson says. Raised in the cottage country of Ontario’s Muskoka region, 20-year-old Thompson has winter dressing down to a science. “I couldn’t live without my vintage Max Mara coat, it’s like a blanket,” he says. At work, Thompson favours practical pieces such as white sneakers and turtlenecks, but after hours it’s a different story. “I definitely like to dress more impractically, like an oversized sleeve that I can barely text in, or boots with a heel just high enough to slow me down.” Some of his statement pieces include a mint-green suit with matching beret and a rhinestone-covered black velvet jacket. “One thing in life I will always appreciate is a fully thought-out, head-to-toe look.” It’s a level of commitment that Thompson is certainly not one to shy away from.

Halifax-based designer Maggie MacCormick has built a reputation on creating thoughtfully crafted wardrobe staples such as jumpsuits and wrap dresses, and she adopts a similar “easy, functional” ethos in her own way of dressing. “I think my style changes a lot based on how I am feeling and what is going on in my life,” she notes. “So maybe it says that I am adaptable and kind of open.” Drawn to thrifting and Canadian brands such as Tony Chestnut and Marigold by Marilyne Baril, MacCormick embodies a highly personal approach to style – one that incorporates treasures found on trips abroad with artisanal local offerings, adding the flourish of florals and artful earrings to elevate her outfits. And there’s a persistent element that guides her approach to dressing, too. “One of my earliest style memories is from Grade 5, when I got a pair of green suede Adidas Gazelles. … I kept them for years, and I think they represent a sort of aspirational aesthetic for me,” she says. “There is this consistent look I try to achieve at different points every summer – I would describe it as 1970s gym class; it’s kind of defined by vintage athletic wear and that specific shade of green.”

When you spend your youth flipping through Vogue, Elle and Harper’s Bazaar, the likelihood of a style fixation creeping into your adult life is quite high. Katrina Olson-Mottahed, Calgary-based content creator and director of the Canadian International Fashion Film Festival, not only indulges her fascination with fashion through her career, but also by treating herself as a walking work of art. Olson-Mottahed can be seen sporting pieces from brands ranging from Fendi to Montreal’s Unttld and Marie Saint Pierre, and she counts fashion-forward e-commerce site Ssense as a go-to shopping destination. Though Olson-Mottahed is a devoted champion of design – “[I hope] my style shows that I deeply appreciate the designers who make beautiful pieces” – she’s undertaken quite the challenge for a fashionista. “I am having a sustainable 2019, which means I will do absolutely no shopping for this entire year,” she says. “I am taking a year to really appreciate what I have and work my pieces into my life.” While she can rock her treasured wild Gucci accessories on an evening out, Olson-Mottahed admits her workday wardrobe leans on more classic accents. “It is easy to look put together when you cover up with a beautiful coat, big sunnies and a nice handbag,” she notes.