Tommy Ton, the acclaimed Canadian photographer who helped define and document the rise of street style photography, has spent over two decades capturing how fashion enthusiasts around the world express themselves through clothing. The 40-something Montreal native, who created the influential blog Jak & Jil and has worked with major brands including Dries Van Noten, Louis Vuitton, and H&M, reflects on his career journey and the evolution of personal style in the digital age.
Ton's path to becoming one of fashion's most recognizable street style photographers began in an unexpected place. Growing up in a Vietnamese Canadian family in Ontario, he would beg his sister to record Fashion TV episodes so he could study designers. After interning at a small Canadian fashion company during high school, he landed a job at Holt Renfrew, a major Canadian department store in Toronto, where his passion for real-world fashion began to crystallize.
"I didn't know it was called street style then. I'm not sure it was called street style then," Ton explains. "But I was so interested in life outside the runway. I was curious about how people actually wore clothes." Walking through Toronto streets, he would spot recognizable pieces like McQueen skull scarves or Chloé Paddington boots, fascinated by how individuals styled high-end fashion in their daily lives.
While working in a corporate retail office, Ton launched Jak & Jil in the early 2000s as an outlet for his photography. The timing coincided with the first wave of accessible website creation, allowing individuals to share their unique perspectives with a global audience. He describes his process of hunting for subjects as similar to being a taxi driver – sometimes finding multiple subjects quickly, other times searching extensively for the perfect shot.
"People still ask me, 'Tommy, why do you always shoot outside fashion shows? What about other places?' And I love other places. I do shoot other places! But it's like going fishing. You want to go to a pond where you know there will be fish. And fashion shows have the most fish," he notes.
Ton credits French Vogue editors Carine Roitfeld and Emmanuelle Alt with dramatically shifting perceptions of how fashion insiders dressed around 2005 and 2006. Before their influence, there was a widespread misconception that fashion people wore exclusively black clothing with oversized glasses, resembling Edna Mode from "The Incredibles." The French editors presented a different image – sophisticated, adult women who appeared effortlessly put-together without trying too hard.
"Everyone thought fashion people wore all black. Then Carine happened," Ton observes. Roitfeld's signature look – Alaïa boots with laser-cut lattice work, tight pencil skirts, black denim, and medium heels – became incredibly influential. Her natural habit of draping oversized blazers over her shoulders after hot fashion shows sparked a global trend, though Ton notes many people missed the crucial detail that such styling required exceptionally well-cut garments.
The early 2010s brought another wave of influential figures, including Eva Chen, Lauren Santo Domingo, and Taylor Tomasi Hill, along with their assistants Danielle Prescod and Laurel Pantin. Ton calls them "the Teen Vogue Girls," noting their stark contrast to the French editors' aesthetic. These women stacked bracelets up their arms, mixed colors and textures boldly, and paired unexpected items like lace blouses with denim jackets or sports jerseys.
"They were just fun. They'd walk by, and you'd see the whole street just smile, like, 'Wait, I can dress like that? And still be cool?'" Ton recalls. The movement gained serious commercial recognition when blogger Susie Lau began booking Gap campaigns based on her "Susie Bubble" persona, while Leandra Medine's "Man Repeller" blog popularized concepts like "arm parties" with multiple bracelets.
By 2014, "influencer" became an official professional designation, marking a shift in street style culture. Ton noticed more people began dressing for cameras rather than personal expression, which he can easily detect through his lens. "You can tell when someone is stressed out about how they look or wondering if they look the way other people want them to look. It doesn't matter how many bracelets you've got on your arms. If you don't love it, it's not a party."
The impact of street style on mainstream retail became particularly evident through Jenna Lyons' work at J.Crew. The brand's aesthetic featuring French tucks and mixed patterns originated from street style photography, helping J.Crew achieve luxury status through accessible styling rather than expensive materials. Ton observed rapid translation of trends from fashion weeks to chain store windows, with styling techniques like mixing stripes with florals or pairing socks with open-toe heels appearing globally within weeks.
"I actually love that part of the equation, because street style is not dependent on your spending budget. Style is about your choices, not your money," Ton emphasizes. He has photographed compelling outfits that combined pieces from luxury houses with items from gas station minimarts, demonstrating that personal style transcends economic barriers.
While acknowledging that people in major cities like New York and Toronto are better dressed than previously, Ton notes a downside to increased access to fashion imagery. The rapid circulation of identical visual references has led to more uniform dressing, with only those who understand subtle details – better tailoring, unexpected color choices, or shoe alternatives – standing out as having genuine personal style.
The recent trend toward "quiet luxury" particularly concerns Ton, who sees it as people attempting to appear wealthy rather than fashion-informed. He contrasts this with genuinely stylish minimalists like Inès de la Fressange or Elissa Santisi, who understand precise fit and have mastered their personal uniform through years of refinement. "People who understand how to dress within a uniform are so compelling to me because they've mastered a ritual in their life, and that ritual has built their personal style."
For aspiring style enthusiasts, Ton's primary advice involves reducing phone dependency and increasing real-world cultural engagement. "Living your life through your phone takes away the experience of living in the world, and that's a real drain on personal style," he warns. In Paris, he encourages people to observe local styling details like brooches on backpacks or the current trend of carrying multiple bags simultaneously – pairing luxury Chanel pieces with casual grocery totes.
After two decades in street style photography, Ton has developed an instant ability to read people's fashion preferences and values through their clothing choices. He can immediately identify minimalists versus maximalists, or distinguish between someone devoted to The Row and Khaite's aesthetic versus another person mixing thrifted Chloé pieces with Marine Serre and Adidas. These visual choices communicate personal values and lifestyle approaches more effectively than any verbal introduction.
Ton finds himself particularly drawn to women over 40 and 50, who demonstrate confidence earned through rich, varied life experiences. He also admires contemporary retailers like Chloe King and Roopal Patel, whose styling makes it impossible to distinguish between Uniqlo and Phoebe Philo pieces. "You feel intrigued by what they're putting together. You don't have to totally get it at first. I don't always, and that's okay. That's great. You need those fish in your pond," he concludes, emphasizing that mystery and personal authenticity remain the most compelling elements of genuine street style.
