The global business that is street style photography today was initially an amateur pursuit. It started with a couple of point-and-shoot cameras, two first-of-their-kind blogs, and a pair of guys with singular points of view. Before fashion shows became the #content circus that they are, with celebrities and influencers posing for hoards of photographers and publicists herding buyers, editors, and VIPs through barricades, they were insular, if glamorous, events. But then came Phil Oh and Tommy Ton, leading a generation of photographers-turned-bloggers, who leveraged their fashion fanaticism, curiosity, and taste to make the scene outside the shows the main event.
Other lensmen preceded them. Bill Cunningham reported for the New York Times from 1978 to 2016, and Shoichi Aoki, the founder of the cult street style publication FRUiTS, captured the evolution of Japanese street style through the aughts. But Phil and Tommy were unique in their focus on the street style outside of fashion shows. Posting to their blogs “Mr. Street Peeper” and “Jak Jil,” they granted their followers access to something that once felt niche and restricted.
This was 16 years ago, and in the years since, street style has become a global phenomenon. Graduating from their blogs to legacy fashion publications, Tommy shot for Style.com, which became Vogue Runway in 2015, and Phil was first a photographer for Vogue.com and now he contributes here at Runway. Brands were quick to notice; these days they spend tens of thousands to dress public figures at their shows, but these two are always on the hunt for the authentic moment.
This week, Phil and Tommy are guests on Vogue’s The Run-through podcast. If there’s something to take away from the conversation, it’s that they know each other’s work better than anyone, even if they’re as different as night and day. The two have been friends for as long as they’ve been photographers. Tommy is an optimist and competitive. Oh is a self-described pessimist with what he calls a “doesn’t really care” attitude. The first thinks of himself “as a fashion enthusiast before a photographer,” and the latter “sort of fell into this backwards.” Their dynamic is as unique as the spaces they’ve built for themselves in fashion, but don’t take my word for it—read the transcript of our interview or listen to it. And don’t miss their edits of each other’s oeuvre.
Listen to the episode here, and read a transcript of the conversation below.
Tommy on Phil
Phil on Tommy
Read a transcript of the conversation below.
Laia Garcia-Furtado: This week on the show. We have two of our favorite OG street style photographers in the studio to chat with us: Tommy Ton and Phil Oh. They know each other and have been friends for a long time and it s really great to have them together because they really are a package deal.
Jose Criales-Unzueta: Before we start, can you introduce yourselves?
Tommy Ton: Hi, I am Tommy Ton and I m a photographer. A street self photographer. I guess if you wanna be more specific.
Phil Oh: Hey, um, my name is Phil Oh, pretty much do the same thing Tommy does.
JCU: Street style photographer. Yeah.
LGF: Two icons icons of the industry.
JCU: Icons, yes. So can you guys tell us a little bit about your personal histories? How did you get into photography?
TT: I kind of started in high school. I m primarily a fashion enthusiast before a photographer. So I felt like playing around with photography was an interesting way to dabble in fashion. I don t think I had the patience for film, so that didn t last very long. Fast forward, to 2005 when I wanted to start a lifestyle website.
This is before blogging, and [I felt] this medium of street photography was a way for me to network and meet people in Toronto—which is where I m from originally. So that s kind of how I started. I just bought a camera and was shooting automatic. I got bored very quickly with shooting in Toronto because it s not a fashion capital; so when I went to Europe for the first time in February 2007, I became instantly hooked to the idea of shooting street style. And that s where I met Phil. Randomly, I think on the second-to-last day of Paris Fashion Week when he asked to take my photo because I was wearing Jeremy Scott.
JCU: Oh my God. Amazing.
PO: The French fry sweater..
TT: The food fight hoodie.
LGF: Do you still have it?
TT: Oh, of course, yes.
JCU: Period. It’s giving archive.
TT: I tried to pass it down to my nephew, but he was just like, no, I don t want it.
JCU: What about you Phil? How did you get into photography?
PO: I sort of fell into this ass-backwards. Like I didn t have any background in either fashion or photography, but I was traveling around to Paris and London and Tokyo just to hang out, and I figured I needed to think of some way to justify going. So I thought about doing a street style blog, but there were already three at the time—that was that I knew of—The Sartorialist, Hel Looks from Helsinki, and The Face Hunter. So I thought, oh, is it really corny if I start a fourth street style blog? I mean, there s already three…
LGF: That s so pure.
JCU: That s so Phil.
PO: So I, okay, if I add all these cities and then I tag all the photos with the brand that they re wearing and the style, you know, like polka dots or plaid which, now sounds common, everything is tagged, but at the time it was sort of a novel thing. And I just had a cheap point and shoot camera from Costco. A couple years later, after I started my blog, Seventeen magazine asked me to shoot an editorial. I don t think they knew that I didn t really know what I was doing. I mean, they quickly found out once I got to set. I figured, okay, I guess I m a photographer now. I started going to fashion weeks because I used to stand outside of cool stores like Seven on Orchard or Mercer Street, Opening Ceremony or Tokyo Harajuku, but I d have to wait hours and hours just to get a couple of photos. I thought fashion week might be like shooting fish in a barrel: I can get a whole year s worth of content in an afternoon.
TT: He said afternoon – that s when he woke up.
JCU: Yeah. No morning shows for Phil.
PO: No.
TT: Still to this day?
PO: Sometimes.
JCU: How would you guys define street style photography? What is street style? What is street style photography?
PO: Well, a pessimist would say it s, you know, a glorified paparazzi. And what would an optimist say?
TT: Well the idea of street style photography was what people were wearing on the street. That s what it was defined by obviously Bill Cunningham and [Shoichi], the photographer that created that book Fruits. So then this idea of street style that happened outside of fashion shows, it was kind of like this manifestation of the intersection of um, blogging and digital with fashion.
So all of a sudden, what people were wearing at the shows became this idea of what street style was. And then obviously through many years of different iterations of it, it became this whole social media craze where people were documenting what they re wearing outside their home or randomly on the street in Soho or whatever. The craze really started from fashion shows. Yeah.
LGF: When you started 10, 15, 16 years ago, what was the scene back then and what is it like now?
PO: Well, at the time—at the very beginning—there were so few photographers that everybody you wanted to photograph, we would stop them and ask, ‘hi, my name is Phil, can I take a photo of you for my blog?’ And it was just so relaxed and easy. So you had time to build relationships with these people; well, the ones who said yes anyway. And as it got more and more popular, you know, since there s no barrier to entry to doing this, more and more photographers started showing up.
TT: It started blowing up in 2008, I would say in the first two years. You could see the numbers increasing, like that was already freaking us out just to see at least 30 to 50 other photographers and now to see hundreds, to see 500 photographers outside an event where only maybe 200 people are invited—it s like we re outnumbering the amount of guests. As opposed to back then, when you could count the amount of photographers on your hand. Which was me, Phil, and Scott or Bill Cunningham. But now it s, it s become more popular than the fashion shows itself.
JCU: You know, you both started as bloggers and the advent of blogging in itself, that sort of became this massive movement in fashion, and eventually you started working with publications like Style.com and eventually Vogue Runway. Tommy. How did you start working with Style.com, which is basically what Vogue Runway is now.
TT: RIP Style.com. I mean, I never had the intention of working for Style.com. I know Scott was initially shooting street style for Style.com. When I started shooting street style, it was for my blog, Jak Jil, and when I started sharing my photos on this blog, that s when people started realizing, oh, there s this different aspect to Fashion Week, because I was a little bit more detail focused. In 2009 when Scott left his position at Style.com that s when [someone] reached out [for me] to take on that role. You know, for a kid in high school who would spend his lunchtime looking at Style.com in the computer lab, I was freaking out. Like, this was an opportunity for me to showcase my work on a larger platform because it was such a huge audience.
And this was before we were looking at websites through our mobile devices or through social media apps like Instagram. So the coverage you would see from Fashion Week was from one particular source, which is Style.com.
LGF: For people who may not be familiar, Tommy had a very specific style, and an obsession with shoes, I feel like would be fair to say. So you got really incredible closeup shots of feet, which I think is interesting because now it s also so much about who is being shot, whereas before it was truly more organic, like what is the thing that s being worn as opposed to who is the person wearing it?
TT: Yeah. I wanted it to come from the perspective of someone that really loved fashion. So for me it wasn t always about who I was shooting—although there weren t celebrities or social media influencers attending. It was more about like, oh, you re wearing that Balenciaga shoe from 2003 or whatever. I was just focusing on that.
JCU: And what about you, Phil?
PO: When Vogue.com was launching-slash-relaunching at the end of 2010, Scott and Tommy were already taken, so I was the next one in line.
LGF: Yeah because there was a time that Style.com and Vogue.com existed simultaneously.
PO: A photo photo editor reached out and, you know, I don t wanna sound like I m rehashing the story of the Devil Wears Prada –
TT: Oh no, please do.
PO: But like, I knew the name was important, but I didn t really know; so I just went in thinking, ‘sure, okay, a job’. You know? I got bills to pay, and then I guess they hired me. I don t really know else what to say. I mean, I didn t really understand what it meant.
JCU: And how has that changed over time? Because I think what s interesting is that your street style photography has become synonymous with Vogue street style coverage. So how has that impression of what it means changed over time? So many people look at the photos that you take every season.
TT: For someone that s been a fan of Phil’s work and seeing the trajectory and where it s come from, his Street Peeper days, like he knows so much more about clothes now and he s very particular about who he wants to shoot. It s happened very organically for him. Like it s a learning experience for Phil.
Because it s not just you know, oh, you re pretty, I wanna take your photo now . Phil’s just like, ‘Ooh!’, like it really catches his eye. Cause he s very specific. So if you look at Phil’s photos, initially there was less chaos, but now he really embraces the chaos. And that s what he thrives on, right?
LGF: The chaos is great. The chaos and composition, Phil?
PO: Yeah. You know you press the button enough times one of them is bound to be right.
JCU: This is Phil.
TT: He has a signature about what, [and] how he shoots. If you see a busted-ass face in the side of a corner of his photo, you re like, oh, that s a Phil photo .
LGF: Someone giving side eye.
TT: He s capturing the realistic chaos of fashion week.
PO: Well, you know, we take thousands of photos every season. I want to try to make the pictures as memorable, or as funny, or as interesting as possible. Otherwise it s just, oh, here s another great outfit . I try to make it as interesting as I can just for my own personal—
JCU: You gotta keep yourself interested.
LGF: It’s your eye. That s what we want from people.
PO: Like Tommy said, Tommy, you know, grew up being an enthusiast. He s an encyclopedia of fashion. Whereas me, having zero background or interest really in fashion, it was all a learning process that I picked up over the years.
LGF: And there s value in both things. And that s important for people to know as well, that you can discover things as you go along and that the “untrained eye” is still valuable and important and brings something unique.
JCU: Yeah, and there s something very interesting about this sort of like very encyclopedic approach to fashion and being like, oh, I want to photograph that because that s a really like iconic piece . Or looking at something and just being like, that s a really cool outfit , or that s an interesting photo , or that s an interesting person , which you both do because you do that too, Tommy. You re also attracted to like interesting people or the way people [are] put together.
TT: Yeah. I m very specific, like if, if someone s at least two blocks away and I ve realized I missed the moment, I ll still run after them. Whereas Phil will strategically be standing there and be like, oh, there s some shirtless guy jogging right now, and he s all sweaty. I m gonna wait until you ve crossed paths with… well, I don t wanna say who. But he s very strategic, like he s waiting for a specific moment where he wants to frame this really funny, candid moment. Whereas I m like, oh no, no, no. I need to shoot this Celine shoe against this backdrop. And it may seem boring to some, but like that s just the contrast of having a different point of view to Phil.
JCU: It s just ‘the eye has to travel the eye’.
PO: You think about this way more than I do, I mean Jesus.
TT: Well, I m working on a book, so I have to think about this constantly.
JCU: So actually speaking, speaking of –
LGF: Some people have been waiting for this book with breath that is bated including us.
TT: I m so sorry it s taking so long.
JCU: So tell us a little about this process of working on a book.
TT: Well, I started the process like seven years ago. I know it sounds ridiculous—how could it take so long? But the thing is, when you take millions and millions of photos you re kind of questioning, why did I take so many photos? So, through Covid until now I ve sat down and really gone through everything and realized, you know, I can t just do a photo book for the sake of it.
I can t give too much away because my main competitor s sitting across the table from me.
JCU: The girls are fighting!
TT: Well, something you should also know about me—and Phil will say ‘a hundred percent’—is I m super competitive. Always. Since day one.
LGF: We love friends who are competitors. That s beautiful and healthy.
PO: Well, I think one reason why our friendship has maintained so strong over the years is that Tommy’s very ultra competitive, but I really don t care.
TT: He says that, but he does. To a certain extent.
PO: But to the point where it never became a problem.
JCU: I love that.
TT: Well, the funny thing is, so because I don t have the Style.com platform where I m shooting and sharing photos every day, if I see something and Phil s just talking away I have to scream. I m like, ‘Phil! Get your ass over there!’
JCU: I ve absolutely witnessed this.
TT: Exactly. You ve seen it. Where I m like, ‘stop talking!’
JCU: Well, the thing is also like, what s funny is Phil also knows everyone at, at fashion week. Obviously Tommy as well, but people are distracting Phil.
LGF: It s a social job.
JCU: Yeah. It s a very social job. You re both very good at it.
TT: It s exhausting.
LGF: I wonder if you ever stop and think about the way that your work actually has changed this sort of very specific aspect of fashion week; like businesses and people. People dress to be photographed outside, it s this whole ecosystem. Like, yes, Bill Cunningham was doing street style before and there were all these people, but I think the specific phenomenon that exists right now was you two.
JCU: Do you ever think about that?
PO: All the time.
TT: You do?
PO: Well, you know, I guess you hate when people are like, ‘Oh, back in the day everything was so much better,’ but you know, in the early and mid years of our respective careers, you could say that the photos that we took sort of documented what people were wearing, the outfits they put together. So trends were created out of the street style photos. So in a way, the men and women in the photos, and Tommy and I, I guess unknowingly collaborated. We created trends that designers or stylists or consumers would react to. But I think with the rise of influencers and celebrities at shows who are dressed in head-to-toe runway looks by the brands; [now] brands have sort of snatched back that control of creating trends by setting the trend of ‘this look 36’.
JCU: So to contextualize that further for our listeners: now a lot of people will show up to shows dressed by brands. And what happens is that brands are trying to make the street style the show outside of the show, which is, you ll put these people, influencer, celebrities, whatever, editors sometimes, in the clothes that are currently in the store. So now you re not only selling what you have on the runway, but you re also selling what people are wearing on the street. So there s less, less looks that are organic, and what people actually wanted to wear. And there s a lot more of like a lot more a strategy. If street style at the beginning was something truly like, intrinsic to the person s style, now as a whole, there s a deck and there s a strategy, and there s a merchandising plan all around Phil hopefully taking a photo of that person, hopefully Tommy taking a photo of that person, and [that person] posting it. It s become an entire ecosystem, as Laia said.
TT: It s a marketing exercise. Because fashion week street style was very focused on editors, or buyers, or stylists, and they were the ones that were just dressing for themselves. There was no brand dressing them. They weren t under a microscope and that was why Phil and I were interested because what we were seeing, what people were wearing, it wasn t editorialized. It was very accessible and it was inspiring, and it was just different from red carpet fashion, right? So kind of when that really blew up with the whole social media introduction, I think that s when people realized, oh, fashion week is a public thing where I can show up and be photographed.
So I think when brands started realizing, oh, here s a marketing opportunity where it s not gonna cost us x amount to place advertising in your magazine.
JCU: Make it an advertorial.
TT: Make an advertorial. And it s free advertising for us, because it just trickles through so many different channels. Right? So I think that s when it totally flipped around and it started becoming less about the insiders and more about these people that were also brands on their own. Because everyone started establishing their own profile. So that s kind of like how influencer culture kind of—in my opinion—originated from fashion street style photos.
LGF: Speaking of insiders, at the beginning when street style was just editors and buyers and stuff, it was still sort of early internet so you re reading names on a magazine and you sort of maybe know what some of the editors look like, but you also didn t. Like Anna Dello Russo existed as a name until she started being photographed like outside of the shows. And it was like, ‘oh my God, this editor has like incredible style!’
TT: You were fangirling.
LGF: Yeah, we were all fangirling. So it also sort of raised the profile of the editors and the buyers to become influencers and stars themselves.
TT: Fashion stars. The heroes of our industry suddenly became the stars of our industry.
JCU: Yeah. And what s interesting is now the photos that you both take, brands use them to promote themselves, but also people use them to promote themselves. Right? Like editors, influencers, people just completely use this content as a way of self-promotion, but also placing themselves in this sort of, ‘Oh, I go to fashion week, I dress well and this person takes my photo.’ Has that impacted your point of view when it comes, or like the way you choose who to photograph and who to not photograph? I m curious.
TT: Yes.
JCU: Go off.
TT: I mean, not to sound shady, but you know, we genuinely really miss the idea of just someone coming and just not caring about the idea of being photographed, or just they re there to attend a fashion show and do their job. So when it becomes this whole parade of just peacocking, obviously you think, oh, I don t wanna photograph that person because they re just so thirsty . Like how would you feel if Brad Pitt was just like turning 360 at every camera? You d be like, ‘oh, this guy is a show pony’, right?
So it s hard when you see people doing that because, I love the hunt of finding someone I ve never met before and just being completely enamored by how they dress. So when you have a parade of people that are coming just to be photographed, you kind of just want to take that big cane and and just pull them off.
LGF: That s a great visual.
PO: Those people are fewer and farther between. You know, there aren t so many young people that start working in editorial, or in stores or department stores, who have the clout to be able to get sent to fashion weeks. In the earlier years, every season there would be, you know, the market editor assistant from Marie Claire Hungary. Like, there were always new people around, but now, with the market forces of publishing…
LGF: … the world s getting smaller.
JCU: It s the same people top level people that have been traveling for a really long time. So there s not a lot of new people to photograph.
PO: But when we do find those new people, it s really exciting.
TT: We re very territorial too.
LGF: Tell me more about your territories.
PO: I don t even know what he s talking about.
TT: Sorry. This is me being super competitive.
LGF: I love that. This is perfect. This is what the people wanna listen to.
TT: Well, you know, sometimes if I can t find the people at the shows, I just use Instagram or social media to find people. So sometimes I ll find people that way and I ll be like, ‘you know, if you come to a show, Phil Oh will be there and he will photograph you, but I will only make sure he photographs you’. So I ll help. I mean, I m strategic in a way where I don t want someone to become overly exposed.
LGF: I love that.
TT: Or I ll be like, are you coming to the show? Can we meet up a few blocks down the street? Just so that you re not bombarded . Because you know the moment someone becomes a street style star, it kind of is a curse.
JCU: It s true. It s a blessing and a curse. Yeah. I m very fascinated by the idea of a street style star.
LGF: I mean, so many careers…
TT: Yeah. It s a different landscape now. It really elevated the traditional nine to five job to another level where, oh, all of a sudden I m in front of the camera. I also could be in a J Crew campaign or walk a fashion show , which in some cases your colleagues would look at you and think, ‘why are you doing that?’ Without realizing, oh, it s actually the next stage in this whole evolution of social media and fashion . You should ask Phil how does he go about determining what shows to go to, and then from what he gets from those shows, why does he fight for a particular image to be the main?
PO: Shit, I don’t know. I mean, how do you explain it? It s ones you like.
TT: I don t wanna say too much, but he s very passionate about a specific image.
PO: Okay. That is true. Like I pretend to be so laissez-faire, but I actually spend way too much time like agonizing over small minute crops..
TT: See, he cares!
PO: Like ‘[I could] do it this way, but you could see the mailbox, the mailbox is blue and it matches the dress’…. Ahh… you know, it takes long time. That s why my photos are always so late.
TT: There was a rare instance last October at the Rick Owens show. Tell the story Phil.
PO: There s nothing to tell cause I didn t get the photo. I waited for like, I don t know, 45 minutes after a show because Eryakh Badu looked like this Rick Owens mermaid. Usually, you know, [I m like] whatever, tomorrow s a new day. If you miss one photo, then who cares?
TT: That s the real Phil. Someone really agonizing over a moment who he really wish he got.
PO: Yeah, but that s you all the time.
TT: Yeah.
LGF: I want to know what happens when you miss something and somebody else captures it. Has it happened with you two?
TT: I can answer that question for Phil. I think the photo he really wished that he got—but he wasn t shooting at the time—so it s not like it was a huge loss., but I think everyone would ve loved to have captured that moment with Virgil, Ye, Don C, Fonzworth Bentley, Chris, Julien. It randomly happened outside of a Commes des Garçons men s show way, way, way back early before I was even shooting for a Style.com. I think there were only two photographers, me and someone else, and they showed up and walked towards us. I mean I wasn t really eager for the photo; I just figured, oh sure, I ll take the photo . Because they just didn t pose for us. And I didn t realize this photo had become such a huge phenomenon and also a precursor of what was to happen [in menswear]. Because Kanye was going shows, but his friends were just there to crash fashion week.
PO: It was parodied in South Park, wasn t it?
TT: It was parodied in South Park, yes. But you know, the funny thing about that photo is each of those guys individually became superstars in the industry. Like it was a catalyst of what was gonna happen. So I wish I was using a better camera and my photo was a bit more focused. But I mean, I m so grateful that moment happened. Working on this project I realized like this photo is so significant because it really showed you what was gonna happen in the future.
PO: Yeah. Me, I, I try to live without regret. What s the point of feeling bad?
JCU: What are some recent moments you photographed that you love, that are memorable?
TT: Phil s photo of Cardi B and Offset where he’s dipping her.
PO: That was a good one. WhenCardi B and Offset were leaving the Balenciaga couture show they were waiting for their car, and I don t know what possessed her, but she started like grinding, grinding her ass agains Offset s crotch.
LGF: She loves her man.
PO: And I was one of the only American photographers there. So I was egging them on…
TT: Yeah, you sure was egging her on. Phil was like, Oh yeah, don t stop, don t stop. Get, get it!
PO: One of the French photo photographers was like, ‘okay, now do something sexy’, and I was like, what the fuck? What do you think she s doing?
JCU: Good one. That is a really good photo. It s true.
TT: Pharrell coming to Junya Watanabe. No one s quite sure if he s coming. His bodyguard comes out holding the million dollar Speedy. He s holding it and then the door opens, his wife comes out, and then all of a sudden you see Pharrell come out and he s reaching to grab the million dollar bag. That I thought was quite a great moment to capture.
LGF: I was just wondering. You know, since social media is a new blog—don t quote me on that—does the way that you used to shoot for blogs changed now that you shoot for social media?
PO: I think there s more pressure to shoot in a vertical, you know, portrait dimensions, because it s better for social media.
LGF: I do like horizontal better.
TT: I like horizontal better too. I used to shoot horizontally way back, and that s how I started off. And I guess I ve become so affected by obviously the dimensions of Instagram and TikTok, so now I shoot primarily vertical. My problem now is I just like more and more and more options. So I m just shooting so much, but it s going towards something. So that s why I have a set idea in mind of what I m shooting, as opposed to just killing time and just taking photos.
PO: Yeah. Tommy will take a hundred pictures of the same person where I ll just go, ‘bloop.’ Okay, move on.
TT: It s true.
PO: You know, sometimes I fuck it up and then I get home and, and I [think I] should have taken a couple more.
This conversation has been lightly edited.
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