What We Wore – Episode 162

Guest: Tommy Ton
Host: Laura Vinroot Poole
Podcast Release Date: September 17, 2025

Overview

This episode of What We Wore features visionary street style photographer Tommy Ton, known for documenting the intersection of fashion and digital culture over the past two decades. Laura Vinroot Poole dives deep with Tommy into his Canadian upbringing, how his obsession with fashion led to a trailblazing career, the paradigm shift he helped spark in the fashion industry, and the challenges and rewards of working independently as a creative.

Key Discussion Points & Insights

1. Early Influences and Childhood ([00:55]–[06:05])

• Tommy grew up in Oakville, Ontario, near Toronto, and recalls a "normal,” outdoorsy childhood.
• First exposure to fashion: His sister’s magazine collages and an episode of Fashion Television featuring Tom Ford’s iconic “Heroin Chic” collection.
• He describes the immediate effect the episode had:

  “From there, I just knew I had to digest as much information as I could about fashion.” – Tommy ([05:13])

• Tommy’s initial dream was to be a designer; he sketched runway looks and strategized early about building a career in fashion.

2. Breaking Into Fashion: Work Ethic & Internships ([07:08]–[13:52])

• Began with menial tasks at a local menswear store and interned with Canadian designer Wayne Clark:

  “I wrote a handwrote a letter and then I mailed it. ... As impatient as showed up, I showed up at their studio and they're like, oh, hi, we just got your letter.” – Tommy ([08:45])

• Emphasizes learning every aspect of the fashion business, from making swatch books to sewing buttons.
• Recognizes that no task in fashion is wasted effort; hands-on experience is invaluable.

3. Shift from Design to Retail, Buying, and Media ([12:03]–[14:46])

• Worked retail at Holt Renfrew, immersing himself in the customer and post-production side of fashion.
• Realized he preferred creative work, fueling his move toward documentation rather than traditional design or buying roles.

4. The Birth of Street Style Blogging ([14:46]–[17:04])

• Launches his blog Jak & Jil in 2005 (early fashion blogging era), photographing Toronto’s fashion events and capturing real people’s style.

• “It was just at the very beginning stages of street style becoming a thing, but it was only seen in publications. It was never really like an online thing.” – Tommy ([14:46])

5. European Fashion Week: Breaking New Ground ([17:04]–[22:53])

• First European trip in 2007; supportive boss funded airfare, Tommy funded the rest.
• Describes the tight-knit, pioneering group of less than 15 street style photographers.
• Recalls the impact of seeing the Vogue Paris team and how candid, real-life images resonated:

  “I was just so seduced by this very slim, skinny silhouette, very sharp and high heels. ... It was almost like witnessing nature.” – Tommy ([20:24])

6. Monetizing & Recognizing the Shift ([21:48]–[25:58])

• Early monetization came from magazine and newspaper assignments; day jobs funded trips.
• First major ad campaign shoot: Lane Crawford, in Paris. The brand specifically requested Tommy's candid, editorial style.

• “I was just, I think I was just really excited to be able to have a job, first of all. And. And the fact that someone was contacting me to do a job on this level.” – Tommy ([23:35])

7. The Dolce & Gabbana Blogger Front Row & Industry Disruption ([26:06]–[30:45])

• In 2009, Tommy and colleagues become the first bloggers to sit front row at a major show, laptops in hand, live-tweeting—a radical move for the then-exclusive world of high fashion shows.

  “So myself, Scott, Garance and Brian Boy were kind of just in shock that we were used as props, basically.” – Tommy ([27:36]) “As I looked, I see my seat is right next to Hamish Bowles and feet away from Anna Wintour. ... I can see everyone just, you know, just looking at me with, like, fire in their eyes.” – Tommy ([27:36])

8. Style.com Era and Impact on Fashion Imaging ([30:54]–[34:00])

• Hired as the official street style photographer for Style.com—the “fashion bible.”
• Tommy emphasizes the editorial, detail-focused approach that set his imagery apart:

  “My approach was not just a person wearing a look from head to toe. I was zooming in on the shoes or a handbag or details. I was a fashion enthusiast, basically taking photos.” – Tommy ([32:23])

9. Transition, Brand Consulting, and the Devoe Chapter ([34:08]–[39:11])

• Post-Style.com, sold Jak & Jil and rebranded under his own name.
• Consulted on collections, fulfilling his “teenage dream” of designing.
• Learned key retail lessons (e.g., “Women like to buy cardigans” – [37:12]), highlighting the pragmatism needed in design versus retail.

10. On the Realities of the Fashion Business ([38:26]–[39:59])

• Discusses the emotional and strategic challenges of commercial fashion—balancing creative vision with market realities.

  “If they can get over their ego and realize that it’s not as harmful as being on Project Runway, it is the reality check that you really need.” – Tommy ([39:37])

11. The Ongoing Role of the Photographer; Personal Projects ([40:25]–[42:01])

• Working on a book chronicling fashion and digital’s merging over the past 15 years.

  “It’s a chronicle of influence where it’s an overview of how fashion and digital intersected in this age, which is the last 15 years, and how that really turned the industry upside down and changed the landscape.” – Tommy ([41:12])

• Expresses love for the people and relationships built through fashion.

12. Signature Style, Influence, and Evolution ([42:56]–[46:01])

• Praised for his recent Celine photos, which influenced Laura’s buying decisions:

  “Your photos from the new Celine collection are the prettiest photos I have seen in so long.” – Laura ([42:56])

• Tommy reflects on what makes compelling fashion imagery—humanity, movement, tactile details.

13. Challenges, Longevity, and Philosophy ([45:20]–[47:38])

• Biggest struggle: Accepting his achievements and wrestling perfectionism.

  “Maybe it's me being a perfectionist ... But then I've realized I just need to let go and just let it be how it should be and not overthink it.” – Tommy ([46:01])

• On his legacy:

  “I helped popularize something that was already existent, but it was all about timing and being a part of the industry when it was going through a significant amount of change.” – Tommy ([47:09])

14. Personal Reflections ([47:38]–[48:56])

• Skipped prom to chase fashion. Most prized fashion purchases: a Prada leather bucket hat and Helmut Lang trousers, paid for by his own hard-earned money.
• Emphasizes pride in self-reliance:

  “I take a lot of pride in the fact that I had to buy a lot of my own fashion or I still do today.” – Tommy ([48:47])

Notable Quotes & Memorable Moments

• On discovery and obsession:

  “It was love at first sight. ... I became really fixated and obsessed.” – Tommy ([05:13])

• On learning through menial jobs:

  “No job is bad in fashion because you learn, you know, 360, like, all the things that need to happen to make it happen.” – Laura ([07:08])

• On the blogger front row at Dolce & Gabbana:

  “I can see everyone just, you know, just looking at me with, like, fire in their eyes.” – Tommy ([27:36])

• On why his style resonated:

  “My approach was not just a person wearing a look from head to toe. I was zooming in on the shoes or a handbag or details.” – Tommy ([32:23])

• On retail wisdom:

  “Women like to buy cardigans ... Because a cardigan can be worn with an even gown. A cardigan can be worn day dress, it can be worn to work.” – Tommy ([37:12])

• On perfectionism:

  “Maybe it's me being a perfectionist ... But then I've realized I just need to let go and just let it be how it should be and not overthink it.” ([46:01])

Timestamps for Important Segments

• Street Style Photography’s Birth: [14:46]
• European Fashion Weeks: [17:04]
• Dolce & Gabbana Blogger Front Row: [26:06]
• Style.com Era: [30:54]
• Transition to Consulting and Design: [34:08]
• On Celine Photos & Influencing Buyers: [42:56]
• Tommy on Perfectionism and Legacy: [45:20]

Tone & Final Thoughts

Throughout the conversation, Laura and Tommy maintain a warm, candid, and passionate tone. Both reveal the love/hate intensity of working in fashion, but agree—despite challenges, it's a uniquely fulfilling world. Tommy’s humility and wit shine as he discusses risk, reinvention, and his ongoing search for personal satisfaction in a rapidly changing industry.

This summary provides a comprehensive guide to the episode’s highlights and will be useful for anyone interested in the inner workings of the fashion industry, the evolution of digital media’s intersection with style, and the personal journey of a street style trailblazer.