162. Tommy Ton | On the Street

Summary

What We Wore – Episode 162

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

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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.

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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])

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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])

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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]

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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.

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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.

Transcript

[A]

Foreign. I'm Laura Vinroot Poole and this is what we wore. Tommy Ton is one of fashion's first street style photographers. Tommy jumped into the industry at a pivotal time in the first moments where bloggers and fashion collided. He's a pioneer of the integration of fashion and digital media and he was born to tell this story. I'm the one person that can claim that I brought Tommy Ton to a NASCAR race. That's true.

[B]

You're the only person that's ever brought me to an event any like that of that magnitude. And I always cherish that memory.

[A]

Well, I cherish that you would agreed to come. Of course.

[B]

I mean that was way back then. I would still go now. I remember so much, but I obviously remember the race and Bojangles and this store. So whenever anyone asked me if I've ever been to Charlotte, I go, yeah, of course.

[A]

The first time we met, I think was with Joseph Altazara.

[B]

Yes. So that was. We hadn't even met before that. You inquired coming down to Charlotte when Joseph was still in his infant stages of his design career.

[A]

As were you.

[B]

Yes, right. It was actually just before the whole saudotcon thing happened.

[A]

You were pretty far along. So tell me, you're Canadian, where are you from?

[B]

I'm originally from Oakville, Ontario, which is just the suburbs outside of Toronto, about a 20 minute drive. So I lived there up until the age of 35.

[A]

And then you're in New York now?

[B]

I'm in New York now. So I made the move in 2017, 2019. Sorry.

[A]

And what do you miss about Canada?

[B]

The people? I mean, I, I miss how incredibly polite we are or. I don't know, I don't want to say we were, I mean we, we still are. Like, we still uphold to a certain way of our manners and our etiquette. But I feel like in this day and age, times have changed a bit and. Yeah, I mean I haven't spent a lot of time in Toronto for quite some time. So I'm not sure how things are. But I'm. I'm pretty sure when I go back there, people don't say. When you say thank you.

[A]

You grew up outside of Toronto in a small town. Was it like how many people?

[B]

I think the population was about 500,000. So okay, it wasn't like a small rural town, but it was like a suburb.

[A]

And what was your childhood like there?

[B]

Quite normal. I really do relish the childhood that I had because obviously I have nephews and nieces now and I look at how they were how they were being raised. And I spent a lot of time outdoors with friends and especially with my parents. So a lot of my weekends were spent going up north and we would go fishing or camping. So I had a lot of time to let my imagination run wild.

[A]

And did you have anybody in your family that worked in a creative field?

[B]

I didn't. I had my brother. My older brother and older sister, they were very much into what was popular in culture at the time. So whether my brother was very fixated on U2 or Depeche mode. And then my sister was very much into Madonna and house and Vogue scene of the 90s. I had two older siblings to look up to. But my sister had plastered her walls with like, lots of clippings of from magazines. So whether it was Claudia Schiffer and the guest ads, I think my first memory of fashion was this cut out of Linda Evangelista from the Chanel Runway. And she had like this seafoam shellacked wig. And I don't know. I can't remember why I was so drawn to it at the time, but I just probably thought, this is just so wacky on the back of my sister's door. So she had cut out all these Runway images and just created a collage on the back of her bedroom door. But she also plastered her walls with guest ads of Chloe Schiffer and Anna Nicole Smith.

[A]

And so you started to become interested in fashion as she did?

[B]

No. So up until the age of 13, I was very much into my own little things as a little boy would. So I like comic books and this. Watching Saturday cartoons and all that and playing outside. And then one summer in 1997, when she was away, she asked me to record with VHS recorder this program called Fashion Television. I don't know if you had it.

[A]

Oh, yeah. Yes.

[B]

She asked me to record it for her one weekend, and I begrudgingly said yes. So when I was sitting and recording it, it was this one episode that was focused on Tom Ford's famous Heroin she collection. It was the collection with the interlocking GS on the G string.

[A]

Yeah, yeah.

[B]

And I remember the moment that segment started and he started speaking. I just became so enraptured and seduced by his choice of words and how he describing the collection. I had seen provocative imagery thanks to Madonna and the Blonde Ambition tour years before, but just seeing how someone was able to create this type of visual imagery and put it out into the world, I was seduced by what he was putting out there that weekend.

[A]

You Saw that. And then what did you do? Were you like, oh, my God, I need to go look at magazines?

[B]

It was love at first sight. So from there, I just knew I had to digest as much information as I could about fashion. So I would go to the library, I would rip out clippings. I would. I mean, I. I owe a lot of money. Money to the public, but it was any way that I could take in fashion, whether it was through fashion programming and typing these specials or weekly episodes and then going to the library, it was just. I became really fixated and obsessed.

[A]

How old were you, Tommy?

[B]

I was 13 at the time.

[A]

Oh, wow.

[B]

This is obviously pre social media. Everything was so prehistoric. Like, I had to find my. Of delving into the culture of fashion.

[A]

So nobody in your family worked in fashion, I gather. So, like, how at 13, did you not forge a path, but, like, even see possibilities as to how you could combine or have this be a part of your life?

[B]

I mean, the initial dream was obviously, obviously, to become a fashion designer. So as soon as I started becoming in love with fashion, I started sketching into, like, a sketchbook. And, I mean, I was very much into art as well. So I was applying these artistic skills towards sketching. Sketching women's clothes. I mean, I was obviously knocking off what I was seeing on the Runway, but adding my own little twist to it. But that was just the seed that was planted into my head that I wanted to work in fashion was to become a designer. Obviously, as I was finishing middle school and then moving into high school, like, as this obsession grew, I started understanding what I needed to do, which was eventually work for a designer as an intern. That didn't happen until 10 or grade 10 or 11. But I was very strategic about how I wanted to forge this career in fashion. So even though I couldn't go to downtown Toronto and visit department stores, I realized, oh, I should work at a. At a local store if I could. So it was a menswear store, and I was vacuuming and folding clothes and doing all the medial labor.

[A]

But I mean, and also it's smart, though, because you. I always say, like, no job is bad in fashion because you learn, you know, 360, like, all the things that need to happen to. To make it happen. A lot of young people want to start and go straight to buying or what. You're like, you probably just need to steam first. Yeah, exactly.

[B]

Push the rocks down the garment district or. So what I did with my internship was it was just a very simple design internship, but at Least I learned the basics of production. I was hand stoning rhinestones on evening gowns.

[A]

Wow.

[B]

So I was working for evening wear designer in Toronto.

[A]

How did that come about? I mean, and were your parents supportive?

[B]

They weren't. I mean, there was a program at school, there was an internship program where, you know, you get to choose, you know, where a work placement. And so I wanted to work for a designer. So obviously the school wasn't responsible for that. It was me. So I had been reading a lot of local Canadian magazines and realized, oh, there's a community of fashion designers in Toronto. So I just saw this one designer named Wayne Clark, and his. He was considered the king of glamour of Canada. I thought, oh, this could be an interesting way to start. So I. I just started. I wrote a letter. I didn't hear from them for maybe three days. And as an impatient teenager, I got on the train, I went down. I went down to the studio and I walked right in and I said, hi. I sent a letter in.

[A]

And I think when you say you wrote a letter, you actually, like, physically, like, wrote a letter and put it in the mail. Right. I mean, because that's also something that maybe it hadn't arrived yet in three days.

[B]

I don't even think I had an email address because this was in 2001. Yeah, this is in the fall of 2001. I wrote a handwrote a letter and then I mailed it. And then as impatient as showed up, I showed up at their studio and they're like, oh, hi, we just got your letter. And I was like, can. Can I intern for you guys? And like, sure, you'll start in February and this was in November on weekends or what?

[A]

When did you go?

[B]

So for four days of the week, I would go to this internship. And then on the fifth day, you would go back to school.

[A]

Wow.

[B]

And report back to the class of what you did for the week.

[A]

Wow. And so really, your. Your parents weren't supportive at all, or what was. What was that conversation like?

[B]

I think they just shrugged their shoulders because, I mean, they. I think they knew that it was just. Just for one semester. So it was just for three months. But then little did they know that this was going to fuel a passion.

[A]

And was your sister still into fashion at this point?

[B]

She was. But the thing is, as I became more immersed into fashion, I realized, oh, her. Her fixation with. With fashion was more of the glamour side of it and just being a happy observer and not being, like, particular about this look from that collection or right So I became really fixated in a way that a comic book nerd would, you know, like, yes, yeah. Every single detail. Or what designer is hot at the moment, Et cetera, et cetera.

[A]

And what was it at that time, other than the. The interlocking GS?

[B]

Well, I mean, this. At the time of the late 90s, this was the era of John Galliano, Christian Dior, Alexander McQueen, Tom Fortigucci, Mitra, Prada.

[A]

Golden times.

[B]

It was a golden era. And it was just. And the thing is, I wasn't very much into the avant garde aspect of fashion. I was more drawn into, obviously, the more glamorous side, which is Tom Ford and John Galliano. But as you become more and more immersed into fashion, you start realizing, oh, there's so much more storytelling with certain designers. So at the time, with Alexander McQueen or Hussein Shalayan, like, these were designers that were being very conceptual with their collections. So it was a very interesting time.

[A]

So you had that month or semester, and then what happened when you got back to school? Were you bored out of your mind?

[B]

They hired me for the summer, and then I was very flattered and then obviously accepted the position. And I still had another year of school, but I think at the same time, they still allowed me to come down to work. I think. I don't know how many days a week, but maybe like a few days, whether it was after school or. Because I had a little bit of taste of fashion, so I felt like I needed to continue.

[A]

And you were doing all the things. I mean, you were sweeping the floors and steaming clothes and, like, everything.

[B]

Yeah, I was doing. What is it that you do when you. I'm already forgetting. When you cut out swatches and you make.

[A]

Oh, yeah. Swatch books.

[B]

Oh, yeah, I was making swatch books or.

[A]

And did you enjoy the. The tediousness, like those. All those projects, did you enjoy it?

[B]

I mean, at the time, I was like, this is not what I was hoping to be doing. But at the same time, I realized.

[A]

But aren't you glad you understand it now?

[B]

Yeah, absolutely, because I know how to sew a button on. And people still question, how do you sew a button? Because I spent months doing okay, so.

[A]

Worked there in the summer and then went back and graduated, graduated high school.

[B]

And then I went back to work for the designer.

[A]

Yeah.

[B]

Then I started having these thoughts of, well, I think I kind of want to work in retail and the buying aspect of fashion. So then I applied for another job. While I was working for the designer with the designer.

[A]

Did you ever meet the clients that bought the clothes and did you ever have that experience?

[B]

I did not have that experience, which is also very crucial.

[A]

Yeah, Yeah.

[B]

A very impressionable teenager that thinks that they can become the next big designer.

[A]

Right. But I mean, I think it's smart that. So your next job was in retail because you wanted to understand that part of it.

[B]

Yeah. So I plugged for a seasonal job at Climatico. I got turned down. I applied for a job at Holt Renfrew, which is Canada's luxury department store. And then I was initially offered a job selling evening wear. But I was thinking to Myself, as an 18 year old, I don't think I could handle this type of clientele. I mean, I guess I made a smart decision. I said, I would love this job, but I can't work in evening wear. And they said, well, why don't you work in accessories? And I said, perfect. So I started working in the sales department, run through selling accessories while also doing the other job working on production.

[A]

And wow.

[B]

Yeah. For the designer.

[A]

Did you connect to the retail part?

[B]

I loved interacting with consumers and having a better understanding of life of a product once it's been shipped to a department store. So then once I started having that appreciation, I thought, okay, so I'm also going to start college and I'm studying fashion marketing. Maybe I want to become a buyer. So I thought there's also a program when you go to college where you intern at the end at the school year. So that's when I thought I would love to intern in the buying office at Holt Renfrew. So once I finished my first year in college, I realized I should intern at Hope Renfrew, which is what I did. And I was in the buying office for a few months and then I realized, this is too boring.

[A]

Tommy, did you have anybody mentoring you along the way? Anybody that gave you advice?

[B]

Yeah, I mean, a few of the buyers were very, very kind and shown me the way. Barbara Atkin. I'm sure you've met her before. Oh, no, you haven't. She was the fashion director. So I had met her a few times and I guess she was very receptive to my energy because I was very excited. And yeah, young in the office is really fun. But then when I was working at Horton Fruit in the buying office and also on the sales floor at the same time, I realized maybe I'm more of a creative person. So this was in 2005 when I started realizing, oh, on the Internet, there's more, there's more to just Going to a website and I mean, blogs were not even existent at the time, but I thought of my own online publication. So this was just prior to blogging becoming something. So I launched my website at the time, which was Jack and Jill.

[A]

Yep.

[B]

You remember, I finished my retail journey and I started working on this online publication where I wanted to be able to feature product but also go and photograph people at parties and events in Toronto. So this 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. And then style.com started featuring street style imagery from fashion shows. And that's when I started thinking, oh, you know, maybe I want to capture this on the street in Toronto. Long story short, I was offered a job with this e commerce site called Vintage Couture. So this woman, Linda Latner, she had hired me and said, oh, you know, you're more than welcome to continue this publication you want to do, but you can also work with me and help me build my online business. So I had left my job at HO Renfrew, but same time I was working for this for Linda and helping.

[A]

Her develop her website and photographing the clothes on models.

[B]

Yeah, I was photographing the clothes on mannequins and just helping an E commerce business for her vintage business.

[A]

And had you ever picked up a camera before?

[B]

No, no, I did, I did in high school. So just for one class, there's one point we were just experimenting with photography, but that was with film.

[A]

And you, you used a real camera. It was, it wasn't your phone, it was always a camera.

[B]

There was no phone cameras at the time. So this.

[A]

Yeah, right.

[B]

The most, the only camera you'd have on, on a phone would be on your flip flow. But even the photography I was taking with my camera, which I bought, was still grainy, but I was still excited to be documenting what people were wearing because I think that was. I didn't realize it way back when I became interested in fashion, but I was really interested in how people dress. But I just didn't understand how I was going to document it and showcase it to the world.

[A]

It's not only how do you document it, but it's also how do you share it with.

[B]

Exactly. And having a platform such as a website or even a blog, that didn't happen until the mid 2000s. So when I started realizing I had this platform and I could capture people just, and socialize and engage with people just going out on the street, I realized, oh, this is an opportunity for me to enter fashion in a way that, you know, it's not so one sided, where I'm. I'm viewing it from my bedroom in my parents house, you know.

[A]

Right, right, yeah, yeah. I mean, and it was huge. I mean it became massive. Jack and Jill.

[B]

It took several years. It took four years actually, because I had launched in 2005, but in 2007, which is when I first started going to the European shows, my boss at the time, she had seen how much I had an interest in taking pictures of people on the street. And she said, oh, you know, if you want to go to Europe, I'd be happy to get you a ticket as a bonus. So that was the real kickstart.

[A]

How did you fund it? How did you monetize it? Even from the beginning, it was all a hobby.

[B]

I mean she, she just said go ahead. She took care of my ticket, which is very nice. I saved my, I paid for my own accommodation. She had luckily connected me with someone in Paris who was able to get me a few tickets. I can't complain that in my first season I had ticket to like Saint Laurent or Chanel, but it was just finding out where the shows were and actually just being outside and seeing a different type of fashion person which I know existed obviously. You know, seeing a movie like the Devil Wears Prada or, or the September issue, you, you have, you kind of have an inside view of what fashion looks like. But when you're physically there at the shows, like because you had been, you've been going to the shows for so many years, you just see something different than other than what you're seeing in a magazine.

[A]

You really do because it's editors.

[B]

Yeah.

[A]

You went to Europe first before you went to New York to do this.

[B]

And I only did London and Paris. That's it.

[A]

There weren't many of you doing it? Oh, there was, right.

[B]

Like probably less than maybe 15. Sometimes even just myself or one other photographer sometimes.

[A]

And did everybody connect and did you learn from them? I mean, were you, was it a generous relationship with them?

[B]

It was fairly easy, like just asking innocently, oh, hi, can I please take your photos? So at the time I didn't know who, you know, who a Karine Roitvel or Emmanuel Alt was or an Anna de la Russo. This is prior to the fashion insiders becoming street style stars. I was just totally just enthralled by the idea of just being around like minded people that loved fashion and just chasing them around the city and just going to different shows and Seeing how they go about their lives in this very short period of time, I just thought was really.

[A]

Yeah.

[B]

But I knew from that first trip I was. I said to myself, I have to go every season from now on.

[A]

Yeah.

[B]

I just knew that I had to be part of this seasonal Olympic super bowl type of experience.

[A]

You know, one thing that strikes me too, and is just when, you know, seeing all these different men and women and how they dress and how differently they dress from Charlotte or Toronto and how just like, mind blowing it is. One of the big things that sticks out for me is something like the Vogue Paris team and just how incredible they looked. And you know, in thinking about that, incredible because they're the chicest, but also because they're riding the metro, you know, or they're. Because of practicalities. Whereas, you know, think about somebody like Ana de la Russo, the heels, like, out of control. She's always in a car.

[B]

Yes.

[A]

You know, and. And the practicalities mixed with like, you know, what you want to look like are so interesting to me.

[B]

It's very true. Because when you go about your day to day life and whether it's Toronto or Charlotte or interesting with the idea of fashion in mind, they're dressing a practical uniform or just this mindset of I have to go pick up my kids or I have to go to work.

[A]

Right.

[B]

So it's just be. And it's so funny that you mentioned the Vogue Paris team because they were the first group of women who I had seen at the Bauman show come out. And I was just so. Just seduced by this very slim, skinny silhouette, very sharp and high heels. And they were just all together and it was almost like witnessing nature. And you're watching this very beautiful group of animals, just.

[A]

Group of peacocks. Yeah.

[B]

Basically walk in front of you without, you know, demanding any attention. And I just thought, oh, this is so interesting. But this is before I even started taking candid photos. I just thought the way of documenting this was asking someone, please can I take your photo?

[A]

Right.

[B]

So after like the whole week and understanding the dynamic of how things worked, I just started.

[A]

Yeah.

[B]

The very last day of Paris was. Just started taking photos of people as they walked by. And then I realized maybe this is the way I should go about it. But it's a bit too late.

[A]

Right, right.

[B]

So obviously the next few seasons when I started finding a balance between taking a very uniform photo, which is asking someone, can I please take your photo? And then also just taking those photos in between of someone getting out of their car, or walking to something. And then when I started uploading these images to my blog, I started realizing, oh, people are resonating more with these types of photos because it just tells more of an editorial story as opposed to just, you know, like a stop and repeat photo.

[A]

Right. Jack and Jill just got bigger and bigger. But when were you first able to monetize it? Did designers ask you to photograph for advertising campaigns at that point?

[B]

So actually I was on assignment for local magazines in Canada and newspapers because they knew that I was the only photographer going to shows in Europe. So it wasn't a very prevalent thing, seeing streetsoft imagery in. In magazines or newspapers, but it was just a kind of a glimpse of. So that's why I started getting commissioned and I was making a little bit of money, but not that much money. So my day job was funding these trips. But it wasn't until the fall of 2008, a year before we met, when I was reached out by Lean Crawford to shoot their Spring Summer 2009 campaign. And initially I thought, is this, like, is someone pranking me? Because the last photographers that shot the campaign were in as a venue. I just. I just thought, why on earth would they ask me? And when I found out that it was a legitimate email, I couldn't believe that.

[A]

Wow.

[B]

My type of photography was being considered editorial to shoot a camp, like an international campaign.

[A]

And so did they fly you to Hong Kong?

[B]

No, they flew me to Paris. So.

[A]

Wow.

[B]

I had never been to the men's or Paris show. Sorry, the men's or couture shows. So I'd gone a month prior to. To shoot those shows, but also shoot this campaign on models in front of the shows.

[A]

I mean, from having, you know, not having studied it in school and having learned just from doing. Were you nervous about, like, your photography equipment or also more the back end of that. Were you concerned about not knowing the language of the industry or of advertising photography?

[B]

No. I mean, when I look back at it now, I think I wasn't. 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.

[A]

Yeah.

[B]

And the thing is, I didn't have any equipment. All I had was just my camera. So.

[A]

Yeah.

[B]

So when they approached me to do this shoot, it wasn't like I thought, oh, I need, you know, assistant.

[A]

Well, that's. I'm worried about, like, assistant and also, like, lighting. I mean, do you get there and you're just like this, we do it just the way I do it and that's it.

[B]

That's how it was. And yeah, and it worked out perfectly. So at the time it worked for that. But obviously when I look back on it, I just thought, oh gosh, why didn't I just hire someone to help me? And it could, I mean I haven't looked at those images but I mean I should revisit it. But it was just so interesting that.

[A]

Some, I'd love to see him, someone.

[B]

Who was just like standing outside the shows wanting to be a part of this, was being tapped to shoot a campaign. And the funny thing is I did a special assignment on as we knew when I was in high school, when I was doing that photography course. So to be the photographer that followed up, followed up on them on a, on an international came was pretty shocking to me.

[A]

Yeah, it's amazing. You for this whole part of your career had been self led and that you photographed things that were interesting to you. And then in this first job from Lane Crawford, you're working with a stylist. I mean are it were some of the looks were you kind of like I would never photograph this or, or had you worked early on with the stylist to say like here's actually what would be interesting to me.

[B]

Well what was smart about the, the campaign was that that they wanted to mimic my imagery and they wanted the models to look like editors. So like got it at the time. Caitlyn Fear, who was the. Yeah where she was working at time but she had a, she still has a very, very signature look which is her, her blonde bob and she like stacks of Eddie Borgo bracelets and other jacket. They styled the model to look like her and love and then some of the other looks, whether the model is wearing Givenchy, they made them look like Emmanuel or like for someone that was really excited about fashion to see how this was a glimpse of a different side of fashion. And I think that's why Declan Chan, who was the one that hired me, he felt like, oh, you know, this is an interesting side of fashion to see it from this perspective. And it's not models wearing clothes, it's models looking like editors.

[A]

And then will you share with me your role in the 2009 Dolce and Gabbana show and how that came about.

[B]

This was actually a month after we met. So that happened because everything started coming into place where so digital media was never really embraced. Bloggers were never really embraced in fashion. And so prior to the Dolce thing weeks Before, I just taken a [e-mail] which is a huge, monumental part of my career. And because of that, that's when there wasn't digital PR branches and in fashion houses, there was just the only PR team. So I think whoever was working at Dolce Gibbana at the time, they realized, oh, there's this new side to media, which is digital. I think we should embrace them, which were the bloggers. So they just had this idea of, oh, let's basically put them in the front row and see how that disrupts the industry.

[A]

And yes, it did.

[B]

At that time, the media or the fashion landscape was always just, you know, editors, stylists, buyers, whoever worked in retail. It was just a very members only experience at a fashion show. So all of this, all of a sudden, to invite these outsiders and just basically place them in.

[A]

It's genius.

[B]

The hierarchy of fashion, and just place them in the front row really caused a lot of disruption.

[A]

People were furious.

[B]

They were furious. And because they. Yeah, they had no idea who we were. And also the fact that they. We didn't bring our laptops, they placed these laptops on stands in front of us. So myself, Scott, Garance and Brian Boy were kind of just in shock that we were used as props, basically.

[A]

Wow.

[B]

And, well, the first, it was two shows. The first instance was dng. So when we were all placed as a group before, there it was. It was quite an impact. But it wasn't until days later when Dolce wanted to do it again, but Scott and Garance pulled out. So it was just me and Brian, but we had no idea what we were walking to. And I had just been outside shooting frantically, and I was sweating and I was trying to look for my seat. And as I looked, look, I see my seat is right next to Hamish Bowles and feet away from Anna Wintour. And I just think I'm. As I. As I'm taking my seat, I kind of look in the corner of my eye, I can see everyone just, you know, just looking at me with, like, fire in their eyes.

[A]

And did anybody speak to you? Or.

[B]

So when I sat there, I. I realized, oh, they wanted me to tweet because they had the laptop screen open to Twitter and whatever. What I was. Whatever I was typing on the laptop was being projected on the screens.

[A]

Oh, my God.

[B]

So as I was typing, Hamish leaned over and he says, oh, what's Twitter? And I had to explain to Hamish, who was sitting next to me, what Twitter was, and I was like, oh, whatever, I'm typing right now. Will be tweeted to a live audience on the Internet or also right now, right in front of us. So he saw what was happening, but I didn't talk to anyone. I hadn't met anyone, whether it was Glenn or Susie Mankeys, but I was just. I was. I was just sweating because I was in so much fear and I had had so many, so much anxiety. I just couldn't believe that this was happening to me. And that from that moment on, that's when I started becoming more invited to fashion shows.

[A]

And I've asked this a couple times, but I'm really fascinated by. I mean, you didn't have an agent at this time, right? No, I mean, I'm just fascinated by you jumping into this stuff alone and not having anybody to ask. No mentor in fashion. But also, I mean, I guess Brian Boy and Garance and Scott, you could ask things.

[B]

Oh, none of us had any representation or that we, we just went into this blindly. The digital aspect of fashion was non existent. Maybe there was. Of course there was style.com and this other site called First View, but there weren't digital publications, there weren't digital journalists, There weren't bloggers that were coming from the suburbs of Toronto, an international fashion show to. To make a mark by being sat in the front row. You know, it was just non existent.

[A]

Did you have friends that you sort of confided in or. Or got support from? Because that seems really brave and really hard.

[B]

I mean, I just talked about it to my other colleagues that were also other photographers. We were all kind of going through the same thing. But when that moment happened, that's when this dynamic that I had with certain editors, when I was photographing them, it was more than just, oh, hi, sure, I'll take a photo. She's like, oh, hey, Tommy, like today. And this was when Anna Della Russo, after that Dolce moment, she came and sought me out and said, oh, you're Tommy, because obviously I can place a face to name now. And I realized she was like, I realize you're Mr. Style.com and Jack, right? So, yeah, having that platform and responsibility was a huge thing, but also being acknowledged as a voice in the industry, that was another.

[A]

And then tell me about style.com. what was that like? And that must have been challenging to go from kind of working for yourself to working for a big corporation.

[B]

It was the fashion bible.

[A]

Yeah. Yeah.

[B]

And it was. It was the website I would log into when I was in high school in the computer lab and printing out looks from the Runway because I remember I came to Charlotte in August, right? Okay, Joseph. So a few weeks after New York Fashion Week had started, and I got asked first to meet with New York magazine and to become their street style photographer. And I thought, great, I finally have an official job shooting for the cut. And then days later, I get reached out by Style.com and they asked me to come to their office. And I was just like, okay, what's this all about? And they said, well, we'd like to offer you our official street style job because Scott has moved on. And I just thought, oh, God, no. I just accepted another. But then I said, it would be ridiculous if I didn't accept this job because it's the dream.

[A]

Dream job.

[B]

The dream job. So obviously, I had to go back to New York magazine and turn them down. And they were angry, but I couldn't care less because I was working for SAO.com and it was just really exciting to be the eyes of so many people that would log onto this site and everyone is looking at the collections, but also to see fashion in a more democratic and accessible way. So 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. So I think that's why people resonated with the photos instantly, because it just felt like a fashion editor's perspective.

[A]

Did they always respect or trust your point of view, or did they try to. Did they want it to look like Scott's look? Were they fine with you being you?

[B]

They were completely fine with me doing what I was doing because they'd seen my photos on my own blog, and that's what they wanted the photos to look like. Because initially it was always vertical images. It was never a horizontal image. So I guess my photos kind of change the direction of StreetSoft Focus Photos, where it wasn't so much, you know, opposed photo that was vertical. It was a horizontal candid photo of someone walking or someone holding a bag.

[A]

And then. How long were you there, Tommy?

[B]

I was there from 2009 until the end, which is 2015. So I realized this past summer that it's been 10 years since stuff.com had folded, but it was a very important time in fashion.

[A]

And you were still in Toronto at that time?

[B]

Yeah, I was still kind of living in Toronto. I was traveling for probably seven to nine months the year. So I'd been doing a lot of work in New York or abroad. So I was always. I was coming home all the Time, but I was always traveling.

[A]

And you were able to do editorial jobs at the same time, or was it full and that became like, a thing?

[B]

Yeah. All of a sudden I was doing campaigns or editorials for international editions for Vogue. It just became such a hot thing in fashion. Was street sports the next thing everyone was discussing? So whether I was doing, yeah, a shoot for Saks and focusing on footwear or going to Dubai and photographing a famous influencer, it was just all across the board. So.

[A]

And at that point, you. You get an agent.

[B]

I hope I got an agent in 2011 and that. Okay, that made a huge difference.

[A]

And then when Style.com folded, what next?

[B]

I realized after Saw.com fold that I wanted to. Well, this is also after I had sold Jack and Jill because I. There was a Brazilian shoe company that wanted to buy the rights to the name. So I just thought, sure, why not? I was very busy. So when I sold, it was 2014. And I realized, you know, like, all my. My energy is always focused on SA.com and. And also, obviously, it was a very lucrative offer. So I. Yeah. But then I just decided maybe it's time to rebrand as myself and not the Jack and Jill photographer.

[A]

Was that scary?

[B]

No, not at all. I felt enough people knew who I was by my name, so that's why I decided to launch my own website under my own name and not continue having a blog under an alias.

[A]

And then you started to consult with brands. How did that come about?

[B]

It started in 2017. So I had been doing street photography for 10 years at that point, and I realized, you know, like, working in fashion is not always brain surgery. You know, if. If you have an idea and then you have a team that can help manifest your ideas, then of course you can be a creative director or designer. So I had made friends with a brand in New York called DeVoe, and I realized, oh, you know, they wanted to launch a women's line. So I thought this could be an opportunity for me to. To have this teenage dream that I had, which is become a fashion designer. So I kind of voluntarily offered myself, and they happily accepted me. So then that's when I helped launch devoe into women's.

[A]

Was it a total fit in that, like, from day one, did you know what you wanted to do and what was missing and how it needed to change or what it needed?

[B]

It definitely was a learning curve because initially I thought, oh, what a great idea would be to have a unisex collection and we create everything to be not just for men's. Sizing or women's sizing, but it's just one size fits all. And the idea sounds great, but realistically when you meet with buyers, you get the questions. That idea was pursued initially and then obviously having some experience with some buyers and realizing, okay, there needs to be a separation between the two. You can't dissock. Yeah, a one size fits all. And then obviously when I learned, when we learned that lesson, we launched a proper women's collection and that's when things were great and I was able to balance that career and also still doing photography at the same time. So that was about like four years of my life. So 2017 to 2021, it was a fun time. But then I realized, you know, at the end of it, it was, it was really hard because obviously going through Covid was a very difficult time. But also just it's, it's not easy managing a business or a brand in fashion. You know, obviously being an American one too, you know, like the demands are very difficult and obviously the realities are just even more difficult. You know, that's another whole discussion when it comes to like talking about exclusivities with certain retailers or.

[A]

Yeah.

[B]

Or certain style. Like actually the greatest lesson I learned during the entire journey with DeVoe was women like to buy cardigans. Because I had a trunk show at Bergdorf Goodman and I talked to the sales staff and I was just curious. I said, oh, you know, what's a really high selling item? And they said, we always sell cardigans. And I hated cardigans.

[A]

That's so funny.

[B]

But then I learned that the reality is women are very self conscious about their bodies and arms. Their arms, right. Because a cardigan can be worn with an even gown. A cardigan can be worn day dress, it can be worn to work, it can be worn home with the kids. You know, it's very versatile item. But the thing is, you can't downplay certain items that will sell. And that's why as a designer, you need to work with the merchandiser because they will tell you what will sell. So as you like a bonded heavy twill, it's not going to perform well if you're selling to or in the south where a woman can't buy that and wear that all the time because she'll be sweating.

[A]

And also just the business of selling a collection, you live with it for kind of a long time, you know, developing it, then selling it, then producing it, then I mean, all the stuff. And it's a, it's A pretty long period. And you could. I'm sure you get sick of was.

[B]

It was so difficult because I felt I was haunted every night trying to think of certain bodies and styles that would not only obviously be new and creative, but also, will it sell? The fun stage, which is designing a collection and being it. Being paraded on a Runway is great, but at the same time, to meet with the buyers and obviously hear about the statistics of what sold or not, you know.

[A]

Yeah. Meeting with the buyers, I'm sure, is, like, the least fun part, actually. I know, because I am one.

[B]

No, actually, I really. I've actually become really good friends with a lot of buyers that would come and visit and see the collection, but I actually do. If I ever did go down that road again, I think it's so important to. To be. For designers to be present with buyers and just listen to what.

[A]

Well, yes, But I will say, too, it's really hard for us because when the designer's there, designers typically maybe sometimes don't really take feedback super well. And so it's really hard to be honest and say, we didn't sell this because it was ugly. You know, whatever. It didn't fit. It made you look fat. Like I. You know, like any of the things. And so you. You'd almost. It's kind of difficult, truly, to be with a designer.

[B]

It can be, but I think if they can get over their ego and realize that it's not as. It's not as harmful as being on Project Runway, it is the reality check that you really need. If you're going to sustain a business, especially this day and age, you really need to listen to the consumer. And obviously, you guys are the ones that are curating the wardrobes of all these consumers.

[A]

Yeah.

[B]

There's no better experience than being in the same room as a consumer and understanding what a woman needs in her wardrobe.

[A]

Totally agree. And that's sort of the magic of it, too. We were talking about it in the store today. I mean, that's just the real fun of it, is to dress a person head to toe and have them walk out happy and excited and like a different person. It's thrilling.

[B]

Yeah.

[A]

After that, you went back to working with brands and doing their editorial.

[B]

Yeah. So since I left Devo, I. Well, while I was at Devo, I was still trying to work on my book project, and I've still been working on that. I realized, you know, I had some unfinished business. So I've been still working on this book project and adding more images to the archive. I am still working as a photographer, but at the same time I'm still trying to finally put together this huge project which I'm still to this day waiting to put out into the world. I'll tell you what it is. It's a bit of, I'll give you a bit of a teaser. 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.

[A]

I mean, I watched it. I mean, you were, you were. It. It's so amazing.

[B]

Well, we were, we were both part of it. We.

[A]

It was, it was so fascinating to watch. Really was.

[B]

Yeah.

[A]

I read an article from years ago that you, when you were asked what, what your ultimate goal was for yourself and you said, my ultimate. I think the ultimate goal for me is to continue. And I just love that sentiment.

[B]

Would I change that answer today? Yes, but I, you know, we're so lucky to work in this industry where, you know, we love what we do and we also get to meet other people that, yeah, are, you know, just like minded and also share the same passions. Yeah. All my best friends and my best relationships are with people that are in the industry. And even when I go, when I'm standing outside the shows and it's extremely hot, my feet hurt. I mean, I'm just lucky that this is what I wake up and I get to do. But I feel like I can only do that for so much longer because I am much older than I was when I started. But I feel like what I've been working towards is. And I know that this is probably what I've been born to do is, was to tell this story, which is what I've been working on. Once I've put it out, I, I feel like it can step back and not be present at every fashion show.

[A]

Well, I feel the same way. I mean, I feel it really. Fashion will wear you down and it will exhaust you and it will test your last nerve. But I do not want to do anything else. I do not. I love it and I hate it.

[B]

Yeah. It's such a love hate relationship. Of course, you know, that we can't pry ourselves away from it, but I find that my relationship with fashion is very different from what it was, you know, 20 years ago when I first became interested in fashion. You know, I don't think I love fashion. I love clothes.

[A]

Yeah. God, Tommy, your photos from the new Celine collection are the prettiest photos. I have seen in so long. They really got me excited about fashion again. And it was interesting because we buy the collection, obviously, and we had written our order and once I saw your photos, we added several things because your photos were so, they were so clear and beautiful and crisp. I mean, I've never seen prettier photos.

[B]

Tell Michael Writer that.

[A]

Yeah, yeah, we'll send them the podcast.

[B]

The funny thing is I, I, so I'm friends with Michael and I told him, I said, you know, like, what's so exciting about what he's done is it's kind of, he understands like, like fans of fashion, but that want to get dressed up again and be excited about dressing and mixing colors and proportions in a certain way. And, and I think he's, he's also like a consumer as well. And he understands like what drives desire and he's worked on very crucial collections with past designers and I think he understands that essence of wanting to excite people and want to pop the collar a certain way or stack bracelets in a different way. So I think it'll be, I mean, we're entering a very exciting time in fashion, but I just think he's someone that has been secretly behind the scenes. And going back to your response to the images, I think it's very important how fashion, whether it's a big photographer or someone that's on the street, how you capture something, whether it's from an awkward angle, that's how you get someone in. Like, that's how you're, you feel challenged to want to dress up in a certain way.

[A]

You know, I think because it feels human or something, like it feels tactile, almost like you can, you can feel.

[B]

It because like in a sea of images that you're bombarded by every day, there has to be that connection in that soul. Right. So I, it was pouring rain at that time and the house wanted me to shoot the finale and I just thought, oh, this is going to be so awkward. I'm just gonna. And they didn't. And they didn't use images, which is fine. That's not why I was hired, but I just thought it'd be a waste of these images ever seen. So that's why I posted them.

[A]

God, they're amazing.

[B]

And that's why it's kind of like, you know, standard one way imagery doesn't always capture a collection in the right way. Like, I love seeing people's videos and photos from their seat, from the show or even the showroom.

[A]

Yeah.

[B]

Sometimes people need to realize you just can't capture an image in a two dimensional way. There has to be some kind of movement and, and kind of like tactile.

[A]

Yeah.

[B]

You know, grip.

[A]

What's been your biggest personal professional struggle in the last 20 years?

[B]

I guess if I have to be honest, it's feeling content with myself and the respect that I already have. I don't know, I feel like I have to prove something to myself, which is what I'm trying to do with this project. But I feel like because I've worked so hard towards something, I feel like this is what I'm going to pour all my energy into words and just making sure that it gets out to the world. But I'm such a. Actually, no, no, maybe it's me being a perfectionist and which is why it's taken so long for me to put out this project. But then I've realized I just need to let go and just let it be how it should be and not overthink it.

[A]

Does being a photographer ever feel lonely?

[B]

No, I, I think in my field of being a street style photographer, it's, it's how I meet people. And yeah, you know, whether it's someone just randomly stopping me on the street or someone I've known for so long and observed them from a distance and just telling, and them telling me, oh, I've been such a huge fan and I'm just like, what? I couldn't have asked for a better life. Being able to work with designers that I look up to, whether it's Dries or skier and then obviously meeting the people that work in the industry.

[A]

So yeah, it's a pretty dream career when you look back at it.

[B]

The thing is, if it was over tomorrow, I'd be fine with it because I've met, I've had a lot of great moments and met a lot of great people, but I feel like what's led up till now, it's just only been half of what's going to happen next. So.

[A]

I agree. And I also think it's really, truly extraordinary. I mean, you really created this thing. This was not a path that was already there. You know, like you completely made this up.

[B]

I mean, I wouldn't say I made it up. I mean, I was, I parted.

[A]

You kind of did.

[B]

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 and. Yeah, and I was just very lucky that I was a part of a small group of people that took their hobby and interest and ran away with it and realized there was an opportunity there rather than sitting back and letting other people come in.

[A]

I can't remember. Remember we've had a lot of Canadian people on, but I can't remember if y' all have proms. What did you wear the prom?

[B]

I didn't go to my. I think it's called formal for us. So I didn't go to mine because I was obsessed with fashion and I was like, oh, I don't care about the high school experience. It was like, I'm more than happy sewing on buttons and sequins at my internship. So I think I just skipped all that and just I. What did I do? I think I was working at my internship at the time, so I just.

[A]

Well, do you have a favorite piece.

[B]

Of clothing of all time or at the moment?

[A]

Yeah, something that's really important to you?

[B]

What is important to me? I mean, I do remember the first few items I bought when I first started making money with my retail jobs, which were which is like a Prada leather bucket hat or a helmet laying pair of trousers with a zipper as the tuxedo stripe. It was just being able to feel like I can obtain, be a part of it and be a part of it and I worked hard for that. Whereas I feel like a lot of kids today, a lot of it's just given to them from their parents.

[A]

Yeah.

[B]

So yeah, I mean 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. At the time I had to work very hard with my part time jobs.

[A]

You're so nice to spend this time with me and I enjoyed it it so very much.

[B]

Thank you so much for having me.

[A]

What We Wore is produced by Capitol and Balto Creative Media. The original song Someone so Enchanting was composed and performed by Brit Drazda. Please follow us on Instagram at whatwewpodcast for additional content and show updates. QueenCityPodcastNetwork.com.