Extravagance Enthusiast

Interior designer and partner at Kalu Interiors, Aleem Kassam has an Instagram account full of glamorous getaway photos, not to mention shots of his swish outfits (and terribly photogenic Bengal cat, Prince Theodoros). "The bulk of my wardrobe is just as well-travelled as I am, as it has come from just that – my travels. What better way to experience a new city, a culture, the people than through its fashion," the 30-year-old Vancouver native says. Kassam, who has a penchant for designer duds ranging from New York-based brand Rag & Bone to Italian icon Gucci, was immersed in the glamorous European fashion landscape at an early age. "One of my earliest and most vivid memories is when I visited Lausanne, Switzerland for the first time with my mother. I think I was about 13 years old," he recalls. "It was a new world to me, one uninhibited or unrestricted by preconceived notions of what fashion should be or is. Everything from your elderly woman in a long fur coat, to the middle-aged man in a bold patterned suit, to a young girl in a vibrant dress with bold accessories…and the bags! The shoes! Purely divine. Everyone had their own style, and it was respected." While his attire can be described as jet-set, Kassam also treats himself at favourite hometown shops including Secret Location and John Fluevog, located in Vancouver's Gastown neighbourhood. – Odessa Paloma Parker

Renata Kaveh

Sultry Minimalist

While she spends her days shooting vibrant fashion images for clients including Dress To Kill magazine and designer Matthew Gallagher, Toronto-based photographer Renata Kaveh – a self-described "dark romanticist with a sense of humour" – is swiftly becoming recognized for her own aesthetic as well. "My friends will often tell me my style changes with my mood and that I'm a human mood ring," she says. "I've also been told I have Helmut Newton tendencies." Indeed, it's easy to see a resemblance between the lensman's provocative images and Kaveh's often daring style. "I think one of the most challenging things about style can be accepting and embracing what interests you, even if it's not trendy, and being brave enough to coordinate those interests through your appearance," she says. "I like to think that, in my style evolution, that bravery sort of faded away and my style expression became a strong, open and unapologetic outlet for my creativity and curiosity." The 35-year-old, who was born in Bangkok, counts COS, Common Sort (a Toronto consignment chain) and Corbo 119 as her favourite places to shop; she also supports local designers, including Markoo, Beaufille and Greta Constantine – the label she sports in this photo. "Greta makes the most lovely silhouettes, always striking the perfect balance of volume, fabric and detail. I always feel mischievous in Greta." – Odessa Paloma Parker

Jeffrey Howard

Offbeat Executive

"The stress of taking school photos still haunts me to this day," says Jeffrey Howard. "I felt as if that image would last forever, and whatever ensemble I chose to sport on that ever-so-important day would be a direct reflection of my personality for my classmates to judge." That's not the case today for the Toronto-born co-CEO of Project Spaces, which creates and manages co-working offices. He has since learned to stand by his clothing choices despite what others might think. "I enjoy playing with the boundaries between men's wear and women's wear, masculinity and femininity," says Howard, who is drawn to unusual pieces that help him stand out in the crowd. The love of the unconventional has led him to accumulate an impressive collection of garments by Wooyoungmi and Juun J, two South Korean designers with international cult followings. He also champions local talent by investing in clothing by Rani Kim and Som Kong, two recent Ryerson University grads. "But my favourite pieces are all vintage that I have picked up during my travels, or pieces my dad wore as a teenager," he says. In the tech real estate sector, Howard's adventurous wardrobe doesn't exactly fit in, but he finds his ensembles often help break the ice when meeting with other professionals who often inquire about his clothes. "Over the last five years, I have realized the significance of making a memorable impression." – Anya Georgijevic

Marcus Troy

Man of Mystery

For digital media entrepreneur Marcus Troy, falling for the siren call of fashion happened early on. "I'd like to say I had an eye for dressing up at a very early age, I would have to say five years old or so," he says. "I always loved clothes and putting outfits together." Today, those outfits strike a balance between fashion and function that's required of his hometown of Montreal, a city known as much for its stylish residents as its inclement weather. That might mean wearing an oversized Raf Simons parka with a suit (he prefers Tiger of Sweden) or Saint Laurent wool blazer, tapered Maison Margiela pants and Red Wing boots. "You want to stay warm, but also look good," he says. On formal occasions, Troy turns to suits and tuxedoes, saying he loves to feel like James Bond. Developing a signature everyday look, however, has proved to be more challenging than appropriating the suave suiting of 007. "I was once told that a really stylish person should have a uniform, so that one day when people see a caricature of you, everyone should be able to figure it out that's you," he says. "I am still working on that uniform." – Caitlin Agnew

Shannon Heth

Chic Chameleon

Shannon Heth has come a long way since "purposefully wearing mismatched socks in Grade 2," but the playful nature of that childhood experimentation is still evident in her creative ensembles. The Vancouver-based president of Milk Creative Communications is a frequent figure on the city's event circuit, switching between looks that are often on the opposite ends of the fashion spectrum. "My style pendulum swings in very different directions. I love minimalism, but I also adore loud prints and volume," says Edmonton-born Heth. "I don't feel I have a signature style; I think personal style evolves and changes as we move through life." Now at the age of 39, she looks to build a wardrobe of timeless quality pieces, gravitating towards the designs of Stella McCartney, Gucci's Alessandro Michele and Mary Katrantzou. While the luxury lover doesn't shy away from an occasional cheap-and-chic indulgence – "I treat fast fashion the way I treat candy: I try not to have too much of it," she says – her most cherished piece is a family heirloom, a fur coat that once belonged to her grandmother, Heth's personal style icon. "She was always elegant, whether in a simple T-shirt tucked into high-waisted jeans paired with her favourite loafers – her uniform for watering her roses – or dining in a full-length sequin gown." – Anya Georgijevic

Alexandre Fida

Natty Nostalgist

"As a kid, my mom and I would visit a potter by the name of Harlan House," recalls Prince Edward County's Alexandre Fida. "He's a very tall man with a Santa-like beard. He often wore a French beret, two different coloured Puma shoes, corduroy pants and an amazing vest. He was my first intro into layering and mixing." Fida, a 30-year-old designer and the second-generation innkeeper of Angeline's Inn in Bloomfield, Ont., says he visits local thrift shops for the charmingly eclectic pieces that have become his signature. "I'm actually really shy, and often feel awkward in certain social settings," he says. "I've discovered, through fashion, an opportunity to show people who I am. I can be bold and brazen. Colour and pattern somehow coax me out of my introverted nature." Fida's penchant for previously loved pieces also extends past the vintage racks. He collaborated with Toronto tailor Philip Sparks on the ocelot-trimmed jacket in his photo; the collar was fashioned out of a coat belonging to his great-aunt. "I like mixing classics from different eras to create an element of timelessness. That being said, I hope that my style comes off as playful and fun. I try not to take myself too seriously and I like to have a good laugh." – Odessa Paloma Parker

Ann Birks

Bon Vivant

"As a young girl I got caught up in the fairy tale stories of Her Majesty the Queen – who was crowned when I was a child – and a short decade later, the magic of Jackie Kennedy. I made several scrapbooks about her Majesty and one on Jackie," says 68-year-old Montreal arts enthusiast Ann Birks, reflecting on her earliest memories of the power of style. "I was captivated by their images. My own style turned out to be something completely different, but clearly I identified with their individuality." Birks, who was nominated by Lolitta Dandoy (a member of Globe Style's inaugural best-dressed list last year), is known for her quirky, creative attire – often topped off with an eye-catching hat. "In the eighties I loved the Netherlands company Oilily, with its emphasis on a bohemian look in riotous colours and patterns stacked on top of each other," she recalls. "Because I honour my clothes, I have a storehouse of coats and jackets from that era when the owner was the designer." Her wardrobe of dynamic pieces, ranging from Dries Van Noten to Issey Miyake, catches the eyes of guests at the fundraisers and events she attends. "I think my dressing style is an extension of my personality, which I would qualify as sunny. After all I was born on the first day of spring," she notes. "I am not a dedicated follower of fashion, nor colour, nor shape. I love my clothes as works of art that have been carefully acquired to withstand the test of time." – Odessa Paloma Parker

Andy Dixon

Avant-Garde Artiste

With a wardrobe that's as vibrant as his paints, Andy Dixon brings a shock of technicolour maximalism with him wherever he goes. "I'm pretty much camouflaged in my studio," says the 37-year-old. Based in Vancouver, Dixon is a self-taught artist who takes a playful approach to his work, touching on themes of wealth and currency in a cheeky manner. This rebellious spirit has informed his choice of clothing since his teenage years in North Vancouver. "I was a punk kid growing up, and I think my natural tendency to subvert culture propelled me towards some kind of counterculture to the counterculture," he says. "Next thing I knew, I was wearing suits to hardcore shows." It's a habit that stuck, and today he's almost always sporting a suit from made-in-Italy brands including Barba Napoli, Reporter and Boglioli. For evenings out, Dixon ups the dandy factor with accessories such as a women's silk scarf worn as a pocket square or a white carnation on his lapel. Day to day, he mixes in colourful thrift-store finds – his favourite being a baby-blue imitation Gucci sweatshirt from the early 1990s – and Nike sneakers, following the street-wise fashion advice of 30 Rock character Tracy Jordan: "Dress every day like you're going to get murdered in those clothes." – Caitlin Agnew

Sophie Hackett

Suited Sophisticate

Having worked on exhibitions featuring photos by the likes of Patti Smith, Irving Penn and Edward Steichen as curator of photography at the Art Gallery of Ontario in Toronto, Sophie Hackett is constantly surrounded by history's most stylish imagery. Born in Montreal, the 45-year-old has an affinity for the tailored silhouette of men's wear, including her navy Junya Watanabe coat and dark brown boots by John Fluevog. "I'm always on the lookout for things that have at once clean lines and some distinguishing – even dandy – detail," she says. While her day-to-day uniform of Naked & Famous jeans and an A.P.C. jacket requires minimal consideration in the mornings ("I just think about it for a few minutes in the shower"), Hackett's sense of style is ever evolving, and it experienced a particularly significant shift when she came out. "I felt another sartorial vocabulary opened up to me at that point, one that suited me more," she says. Her style has also developed a certain sensibility with age. "I think there's something about getting older. My conversation about what to wear is more with myself rather than with some abstract idea." – Caitlin Agnew

Vintage Queen

"I gained confidence in my late twenties and with that came the freedom to be bolder in my choices," says Mo Handahu, a Halifax-based digital content strategist. Handahu, who was born in Harare, Zimbabwe, documents her fearless print and colour-heavy ensembles on her blog Lion Hunter (the meaning of her last name in Tonga), which she shares with her brother Ten. Her love of fashion stems from Saturday shopping jaunts with her mother while growing up in Zimbabwe. "I have fond memories of tagging along with my mom and watching her go through the racks of her favourite boutique," she says. Today, the 34-year-old describes herself as "thrifter and vintage shopper at heart" and scours Halifax's second-hand and consignment shops for unique pieces such as the 1970s theatre costume cape she wore for this photo shoot. Two months ago, she made a daring move (for a fashion blogger) and sold about 80 per cent of her wardrobe. "I'm slowly rebuilding, exploring and challenging my style beyond my obsession with prints," says Handahu who looks to Solange and Tracee Ellis Ross, as well as fashion insiders Frédérique Harrel, Candace Marie Stewart and Gray Castillo, for inspiration. Although her closet may be undergoing a major overhaul, Handahu's style mantra always embodies one word: "Unafraid." – Anya Georgijevic

How we did it

To compile this list, a group of Globe Style editors and contributors (Caitlin Agnew, Nathalie Atkinson, Nolan Bryant, Anya Georgijevic, Odessa Paloma Parker and Andrew Sardone) reached out to their networks of wardrobe watchers, dug deep into their Instagram feeds and surveyed 2016's honorees to create a roster of candidates from across the country. After narrowing the nominees down to 10, photographers in Toronto, Vancouver, Montreal and Halifax were commissioned to capture the subjects' signature styles.

Think we missed the mark and have a best-dressed suggestion of your own? Post a photo of your fashionable contender to Instagram and tag the picture @globestyle and #GlobeStyleBestDressed.

PHOTOGRAPHED BY: Kamil Bialous/Vancouver, Riley Stewart/Toronto, Marie H. Rainville/Montreal, Riley Smith/Halifax

PHOTO SHOOT CREDITS: Halifax - Makeup by Shanea Sparks. Toronto - Makeup and hair by Taylor Savage for M.A.C Cosmetics. Vancouver - Makeup and hair by Jessica Venturi for THEY Rep/M.A.C Cosmetics. Styling by Carla Pederson/THEY Rep. Montreal - Makeup and hair by Carmelle Da Rosa for Judy Inc./M.A.C Cosmetics. Styling by Henri Soumah/Judy Inc.

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