I’m thrilled to bring you Tommy Ton for this week’s Five Fits. Tommy is an outright legend, and he was a huge factor in catapulting street style to its current heights. I spent hours looking at Tommy’s photographs before meeting him. I’m not sure what I assumed he’d be, but I know that he was very different from whatever I had imagined. This person who had taken such prolific, iconic photos was in some ways as nerdy about clothing as me, obsessed with food and the little things that make life pleasurable. He was calm and funny, and even a touch catty if provoked.
I would be lying if I said I wouldn’t stand near him and observe who and what he shot. He’d be talking to other photographers one minute and sprinting the next for the perfect shot. That urgency really stuck with me, just as his work did. After years of unexpected meetings, we became friendly, and have shared many meals and conversations together. I consider myself lucky to know Tommy, and so I attempted to have a conversation with him here much like one we’d have over tacos or Thai.
Below, Tommy and I discuss his big break on Style.com, the [de]evolution of street style and getting “the shot,” wardrobe staples and slowing down purchase velocity with age, changes he wishes to see in the fashion industry, and plenty of other topics.
There’s a lot of information on the Internet about how you started your first blog, Jak & Jil, so let’s skip over that and talk about your street style career more specifically. Which moment felt like your first big break, and how did you handle the increase in workload and travel?
The biggest break for me was scoring the gig at Style.com. Before social media took over fashion, everyone would log onto Style.com as their primary source for fashion. Intuitively, everyone would always type in the Style.com URL instantly when they went online, so to be plucked by the fashion bible and become a contributor, it was a huge deal for me. It was the most validating feeling I have experienced in my career. The workload became incredibly overwhelming when I had double duty between Style.com and GQ.com covering all fashion weeks, but I was more than pleased to be working and sharing my point of view with the world. I don’t think I could do it today because I’m much older, but for that period in my life, I felt immense pressure and joy capturing and sharing content with such a large platform.
I remember when I began my street style career, probably around 2010, there weren’t many photographers out on the streets here in New York. That’s how I had the pleasure of meeting you in the first place. It certainly made it easier to shoot subjects unobstructed. What was it like shooting street style before it really boomed into the behemoth it is today? Do you have any particularly special memories of getting “the shot” that other photographers couldn’t?
I’d say before things got chaotic, it was more enjoyable and you felt more at ease. It’s very stressful now and it gives me quite a bit of anxiety just thinking of going into that physical and mental state. It is what it is and you have to embrace it but there are just some situations where you’re dealing with noise pollution, overly aggressive security or police, and of course crowds. I think “the shot” that gets mentioned the most is the infamous Kanye group photo. It was really just timing and luck but at the time there were barely any photographers at any shows, so in the moment, I didn’t think I got anything special until after it was posted and the response it got. Nowadays I’m not concerned about getting a shot that no one else has, I’m just trying to be present in the moment and observe what is happening.
It was definitely easier to get more natural, candid moments when it was less of a circus outside the shows. It was easier to meet people and develop relationships but I can understand how stress-inducing the experience is now coming to a fashion show. You don’t exactly want to make eye contact because you have so many people looking at you and judging you.
You own a ton of clothes, but I know your wishlist is ever-evolving. Which pieces are you still on the hunt for? Are there any recent purchases or finds you’ve made that you’re happy about?
Yes, I do own a ton of clothes and I have to live with myself for that habit. [Laughs] I honestly think I’m good at the moment not having anything I’m on the hunt for. I do come across a few things I passed on the first time around, but with so many resale platforms available now, it’s easy to have a second chance at owning something you’re still on the fence about. I’ve probably been happiest with just a bunch of running shorts from Lululemon and Asics that I’ve bought for the summer. Sounds really boring, but I think my feelings towards shopping and owning particular designer clothes isn’t the same as it once was before. Maybe it comes with age…
What are some wardrobe staples that you can’t do without?
I have a pair of United Arrows x Gap chinos that I own several pairs of that are a staple for me year-round. My array of Lululemon shorts that I just acquired are what I basically wear now. If I splurge on anything, it’s just great core pieces from Jil Sander. I love what Luke and Lucie are doing at Jil Sander. It’s the most ideal wardrobe.
Fashion has obviously grown so much in popularity since you first found an interest in it, but do you have any advice for a young adult who thinks they might want a career in the industry? How about for someone who has an interest in photography and wants to take it to the next level?
Hmm… you know, fashion is a completely different game than it was ten years ago. I think we’re all trying to find our place in this rapidly evolving industry. The advice I can offer someone entering is to do the homework, understand that everything just doesn’t happen overnight, and it takes years to hone your eye or point of view. I think with the democratization of fashion, so much has changed in the way that not everyone wants to put in the time and learn. There was a time if you wanted to become a stylist or photographer, you would have to intern and assist someone for a long period of time to learn from experience, but because of the digital age, it’s given anyone from anywhere the opportunity to skip all of that.
Where are you most looking forward to traveling to in 2022?
I would really love to return to Japan. I used to go twice a year during a very indulgent five-year period but it’s been five years for me and I’m anxiously waiting for their borders to fully reopen. It’s honestly my favorite place in the world. I highly recommend, if you do go for the first time, you at least give yourself 10 days minimum to visit. There’s just so much to see and do and take in.
What changes would you like to see in the fashion industry?
As much as I’d love for fashion to return to simpler times when it moved at a much slower pace, it evolved for specific reasons. I miss fashion journalism and seeing it be critiqued and celebrated as an art form. Fashion really just feels like a machine and the same level of creativity is no longer as present. The landscape of fashion has really changed and the ecosystem of fashion has been disrupted. Print is nearing its end and the art of image-making is a dying form. People who dedicated their careers to fashion are finding less of a connection to it and because of that, we find less familiar faces as part of the system. It’s a system driven by metrics and popularity, sadly.
You spent some good time with a brand that’s important to both of us, Deveaux. What’s next for you now that you’ve left?
I’ve been working on a specific project that involves a book. It’s been a long time coming and now that I’ve moved on from Deveaux, I have the time needed to dedicate myself to this next chapter and finally get it finished. I’ve mentioned it a lot to a lot of colleagues, but I assure you something special is coming. Stay tuned.
Christopher Fenimore is a writer and photographer living in New York. Working with clients ranging from clothiers to vineyards, he’s also covered street style for a number of outlets. Follow him on Instagram at @c.fenimore.
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