A Retired Teacher’s Unexpected Foray Into Fashion Photography

By Ayla Angelos

For Bobby Lee, a photographer who’s spent the last 30 years unofficially documenting fashion’s biggest names, it’s not about the glamour of Fashion Week. Instead, it’s the simple, human moments. “Some models gave the photos to their mums for the refrigerator,” he says.

When Fashion Week rolls into the cities of New York, London, Milan and Paris, the streets transform into a spectacle of glammed-up figures, each vying for their moment in the spotlight. Positioned at the sideline, on the edge of stardom and glam, there tends to be a different kind of crowd – a pack of hobby photographers wielding cameras as they duck in and out of traffic, their lenses fixated on anyone who catches their eye.

Bobby Lee has been part of this cohort for the past 30 years. A retired maths and computer science teacher from Jacksonville, Florida, Bobby stumbled upon Fashion Week in New York by chance, during a serendipitous stroll through Bryant Park in 1995. He was immediately hooked, and what began as a side interest quickly became an obsession. He has since built a personal archive of thousands of photos, all shot at the fringes of high fashion. Until now, these images have never been published.

In 2012, filmmaker Salome Oggenfus met Bobby while waiting outside the Oscar de la Renta show at New York Fashion Week – a busy event that saw celebrities like Nick Minaj in attendance. As they chatted in line, Bobby excitedly whipped out an album of 4x6 photographs he’d taken of models over the years. Salome was immediately struck by the quality of his work, as well as his great sense of humour. When she asked, “Did you take all these pictures?” Bobby, with a grin, joked that he’d clipped them from a magazine.

The pair have been working together ever since, turning Bobby’s archive into a documentary film entitled Role Models, and a book, Fab Fashion Week Faves, named after one of Bobby’s old Facebook albums where he used to upload his photos. Both are set to release this month.

When I log into Zoom, Salome is sitting cross-legged on the floor, smiling patiently as we navigate decades of technology – phone, Whatsapp, Skype, Zoom – to bring Bobby into the conversation. He doesn’t have a mobile, nor does his laptop have a camera or microphone. Instead, he dials in from his landline. Cheerful and full of energy, he’s fresh from another New York Fashion Week, his Southern drawl cackling through Salome’s phone speaker. We spent the next hour discussing their 12-year friendship, the thrills of capturing the energy of the fashion world, and how the so-called ‘inner circle’ may not be as intimidating as it seems.

Ayla: So how was New York Fashion Week this year?

Bobby: It felt more scaled back. Normally, I’d take around 12,000 photos, but this time, I made less than 4,000. Still, a few wonderful people I love meeting crossed my path, so I’m happy about those moments and choose to forget what I missed.

Ayla: Did you attend this year, Salome?

Salome: My connection to Fashion Week came through filming Bobby, and since that project has ended, I’m quite tangential to the world of fashion now. I am not directly involved anymore. My involvement was really parallel to my time filming him.

Ayla: How did you both come to meet each other?

Salome: It was in 2012, over ten years ago, at the Oscar de la Renta show in New York. We were outside the New York Public Library on 42nd Street. There was a big crowd – I think Nicki Minaj was there. At the time, I already knew Damien [Bobby’s fellow photographer], who I was also filming for the same project. We met when I was working at a casting company, and he was an intern there. I got interested in his fascination with Fashion Week and his photography outside the shows, and I went along with him to a few events. Damien then said, "You have to meet Bobby. He’s the real deal." That’s when I saw your work, Bobby, and we had a brief conversation. Later, I went to Paris and started filming.

It wasn’t supposed to be a decade-long project; I went to Paris twice and filmed more often in New York because I lived there. Sometimes I had other people filming with me, and we would try to meet up with you, Bobby, which wasn’t always easy because you don’t have a phone. We’d show up at shows hoping you’d be there, and most days, we’d follow you guys around. It gave me a good insight into the stamina it takes to attend seven or eight fashion shows a day – it’s pretty demanding.

Bobby: Having someone film me while I was going about my usual routine was something I wasn’t used to.

Ayla: How long have you been doing this for, Bobby, and why do you do it?

Bobby: It all started in 1995 when I was still a teacher. I went to New York for Christo’s installation The Gates in Central Park, and later that day, I stumbled upon Fashion Week at Bryant Park. The people were so open to being photographed, and that’s what drew me in. I retired a couple of years later and by 2008, I was travelling to New York, London, Milan and Paris for Fashion Week. I’ve been doing it every season since.

I’ve always loved street photography, and the warmth I felt from people at Fashion Week kept me going. I bring a book of photos from the previous season and try to reconnect with those I’ve photographed. It’s all about the kindness and the positive feedback I get from those moments. Now, I have a giant bookcase filled with all the photo books I’ve made.

Salome: When I started filming, Instagram existed, but it wasn’t what it is today. Some people used it, but it wasn’t a big thing yet. In many ways, Bobby’s photography felt like a precursor to how people now use platforms like Instagram – connecting with others through the images they take, sharing those images and receiving feedback. Today, that’s a common pattern.

Ayla: Bobby, who catches your eye when you're photographing models at Fashion Week? Who do you want to photograph the most?

Bobby: Well, I’ve come to know many of the greatest models, some for over 10 years. Coco Rocha, for example, I photographed her on a merry-go-round in 2008 or 2009. She did many shows in New York at this time. When you’re photographing someone, you don’t expect to cross paths again. But when you do, it’s a validation that I picked the right ones to focus on over the years.

Ayla: When you photograph the models, do you tend to have conversations with them? Your images feel very candid and relaxed.

Bobby: Often, I do. Some of these people I’ve been encountering for years, while others are brand new models that no one knows yet. But I don’t shut anything out – if you're walking down the sidewalk, you're fair game for me. I’m not photographing to sell; it's all about the kindness and connections I experience. And when I can hand them a photo from last time, that’s when it feels special. Some models tell me they gave the photos to their moms to put on the refrigerator. It’s those little moments that matter to me.

Ayla: Salome, what was it about Bobby’s work (and personality) that inspired you to start this project?

Salome: My main interest in starting this project was about examining the act of taking pictures, why we take pictures, the social function of photography and the exchange of value with images. Bobby very quickly revealed himself to be such a unique, entertaining and charming person that he seemed like a great person alongside whom I could explore these concerns.

Ayla: Salome, how did you want to translate Bobby’s work into this documentary? What was your main goal?

Salome: Honestly, I didn’t have a specific goal. It was more of a journey to figure things out. I knew I wanted the film to be observational and for Bobby to speak for himself without any other people contextualising his work. I wanted viewers to come to their own conclusions. Beyond that, I was just curious and figuring things out as I went along, since it was my first film.

Ayla: How did you navigate consent while filming?

Salome: Since most of what we captured was on public streets, there was not a huge concern around consent beyond the protagonist's consent to be filmed which, of course, was always an ongoing conversation. Over the long time of filming there were times where certain things were off limits. The one thing I will say is that the draw of Fashion Week for Bobby and many other people is that most people who are there absolutely want to be recorded, or want their picture taken. Out of all the people at Fashion Week, Bobby was probably one of the least interested in having his picture taken or being filmed. This was an attractive quality to me in a world where a lot of people want attention and will happily put themselves on display. But there was more of a mystery to Bobby, more to find out.

Ayla: What did you learn from making this film? We’re discovering Bobby’s work, but also about this inner circle of models and beauty.

Salome: Well, I live in New York, and as a creative, you often end up working adjacent to the fashion world because that’s where the money is. For many years, I was part of that world, but making this film helped me recontextualise my experience. I got to think about how creatives relate to the fashion industry and the allure of exclusivity that draws people in. It made me reflect on who’s on the inside, who’s on the outside, and how we all relate to that dynamic.

Ayla: Bobby, what are your thoughts on the ‘inside circle’? Do you ever want to be on the inside, or are you happy being on the outside?

Bobby: I’m not a fashion person, so being on the inside or outside doesn’t really matter to me. The human connections are what reward me. I don’t do it for money, and I’ve never sold a photo. It’s just about being connected to amazing individuals, and that’s enough for me.

Ayla: Do you think you’ll continue photographing Fashion Week or are you tempted to photograph other subjects?

Bobby: If I go for a walk, I’ll photograph birds or the creek, but next week, I’ll be in Paris photographing Fashion Week again. I’m documenting the history of street photography in a way, but I never tell anyone that. I just let the work speak for itself.

Ayla: Do you have any favourite memories or funny moments from when you’re out photographing?

Bobby: Oh, there are many. I try to keep a smile and a sense of goodness when I’m assembling my Fashion Week book. Smiles are my first requirement. I didn’t think about it at first, but now, after taking hundreds of photos a day, I select the moments that resonate with me. It's not just about knowing someone – it’s about capturing that expression of happiness.

Ayla: Salome, do you have any memorable stories from making the film?

Salome: There were many! One time, we had a picnic outside the Tuileries in Paris on the last day of Fashion Week. We’d gather grapes and chicken while they took down the Fashion Week tents around us. It became a simple but lovely tradition.

On the opposite end, one time in Florida, Bobby and I got stuck in a foresty environment with a lot of mosquitoes. We had to climb over a fence to escape – it was a far cry from Fashion Week, but still a bonding moment.

Ayla: Bobby, you mentioned the joy in street photography. Is that a big part of what motivates you?

Bobby: Yes. There’s a sense of history in what I do. I’m not just picking the next person who walks by – I’m making a judgement about exceptional photography. And that’s what keeps me going.

Ayla: Salome, do you see yourself continuing in documentary filmmaking after this project?

Salome: Recently, I’ve been focusing more on live performance, but I’m sure I’ll return to filmmaking at some point. Maybe not another 10-year project right away, though!

Ayla: Bobby, do you have a main narrative or story you hope people take away when they see your new collection of photos or the film?

Bobby: I’m happy with the production and the story we’ve told. Whether people understand everything or not, I just hope they respect it and take away some sense of what’s going on. That’s what matters.

Ayla: Do you both think you’ll work together again in the future?

Bobby: No clue, but I’m impressed with the film. Salome did a fantastic job, and I have a lot of respect for her work.

Salome: We’ll see. Time will tell.

Role Models will be screening at Now Instant on the 8th November and launching the same day on Airtime Online

Fab Fashion Week Faves can be bought in our shop.