Cleo Sullivan is an incredibly talented photographer and artist currently living in the Hudson Valley. Her portfolio of work is vast and ranges widely from editorial projects to solely creative experiments, but every one of her photos has a distinctly Cleo feel. Her work is beautiful, playful, whimsical, and 100% unique. I spoke to Cleo to learn more about her prolific career, her story, and how her work has been influenced by her time living Upstate. 

All photographs below are the work of Cleo Sullivan. 

Where were you born and where did you grow up? 

I was born and I grew up in Pennsylvania. It’s just outside of Philadelphia. It’s called Malvern. It’s kind of like a small town like Rhinebeck, kind of suburban-country.

Do you remember, as a child, knowing what you wanted to be when you grew up?

I think I either wanted to be an artist or a vet.

I feel like I also wanted to be a vet when I was little. I definitely remember having that fantasy.

A lot of kids do because they just love animals. And I think it was that for me. 

And the artist part — can you explain where that came from?

Well, my mom was an artist. And her mom was an artist. So it was kind of an easy decision just because she let me be creative. She wasn’t like, “Oh, you’ll never make money doing that” or anything. She was more like, “oh go to art school! Here’s some paint! Here’s an easel!” She totally encouraged the creative side of me. 

What kind of art did your mom and grandmother practice? 

My grandmother was an illustrator. She did really beautiful portraits of people in pastels that were really brilliant. My mom studied in England, and she studied with a famous animal sculptor. So she did a lot of bronzes, and she did a lot of pastels of mostly horses and dogs. 

What did it feel like for you, as a child, to watch two influential women in your life working in the arts?

I didn’t really think about it, it just felt normal. And I didn’t really know my grandmother. I just know that she was an artist. My mom used to take us out with her when she went to do the portraits of the horses. She would go photograph them and then come home and draw them. But the one really cool time I remember, she did a whole polo team. She did all the horses on the polo team and this one little Shetland pony, which was the mascot and I thought that was really cool when I was a kid.  

I saw online that the first photo you remember taking was of a pony?

Yeah, that was my pony Magic — can you believe that I had a pony named Magic? Isn’t that the cutest thing? 

So have you always had that love for animals?

Totally. I get so upset if an animal gets hurt or anything like that. 

You graduated with a degree in painting from the Pennsylvania Academy of Fine Arts. But since then, you’ve had an incredibly successful career in photography. How did you end up pivoting from painting to photography as your main medium?

When I was in school, I had so many interesting-looking friends that I just ended up shooting them. And because I was super into fashion. I really loved it so much, just like a lot of kids do now. I feel like it’s part of their identity. As a teenager, you’re figuring it all out, and fashion was part of that for me. How I dressed was cool and I just wanted to bring that into my photos. I remember being in a bookstore and looking at all of the fashion magazines for hours. I was just so inspired by what I saw. 

So it started as portraiture?

No, I definitely started more with fashion photography. But as soon as I got off the plane to New York, I found myself shooting so many portraits. It wasn’t like I was planning on shooting portraits or celebrities or anything like that. I was just doing it. One of the first portraits I did was of Lena Horne, and it ended up on page 6!

    Rihanna, as photographed by Cleo Sullivan

How do you feel like your education in painting has impacted your career as a photographer?

Having all that experience with light and knowing what beautiful light is is super important. And also referencing actual painters as inspiration and stories. I do that all the time. There was this speedy story that I shot that was very Klimt-esque. Sometimes I’ll even name a story, in my head, after, like, Picasso’s blue periodfor example. So I’ll end up with a funky set. You know how his perspective wasn’t always exactly right? Like he would shift the floor just a little bit so the perspective is a bit odd? Something like that will be an inspiration for the set, and then the clothes in the blue period will just be all denim or something like that. That’s an example. I reference painting all the time. I think a lot of photographers use artists as inspiration. They use film, too, a lot for inspiration.

Are there any shoots or projects that stand out as highlights of your career?

Getting to shoot Jack Nicholson was a huge highlight, I have to say. When I found out I got that job I was jumping up and down.

Can you talk a little bit about what went into that shoot?

Um… I don’t know if you’re going to like this! I wanted it to be a little weird and surreal and even a little bit pervy. Even when I was shooting Jack, he was like, “how are we going to be using these mannequin arms?” And I was like, “well, it kinda reminds me of you! A little weird and a little surreal.” And he says —— in his perfectly Jack voice that kind of gets under your skin —— “Cleo.” And I said back, “Jack.” 


        Jack Nicholson, as photographed by Cleo Sullivan

I totally get that. I think the image is so interesting and it really fits with the energy he brings as an actor. Is that where you were drawing inspiration from?

Yeah, he’s just really edgy and he took all those really cool roles that really brought him to a totally different acting level. He wasn’t ever just gonna do, like, mamby pamby rom coms, which is fine! But he took these crazy roles, like in One Flew Over the Cuckoo’s Nest and The Shining. He got all the range that he possibly could from all the roles that he took.

So that’s kind of what you were trying to bring out of him in the portraits?

Yeah, I felt like he was so special that he needed a special picture.

When you shoot celebrities in general, do you typically try to bring influence from their careers and their personas into the photos?

It depends on the person. You always want to shoot something kind of beautiful. At the end of the day, I just wanted to shoot very cool and interesting portraits of all my subjects. 

Are there any other moments in your career that also stand out as either influential or very memorable to you?

The first time I shot for French Vogue, or any other time I shot for French Vogue, I was like: I can’t believe I’m here! I thought it was amazing. 

There was another thing too. I remember looking at Fashions of the Times for the New York Times when I was younger and thinking: wow, I really want to shoot for this magazine. And then I shopped for them and it felt like my dream came true! It is so cool that you can actually think of something and then make it happen.

I was looking through your portfolio and I saw that you’ve shot many beautiful portraits of children. You even have an entire selection of images on your website of that genre. How did having your own children influence your work as an artist?

Honestly, I have to say that I never really shot with kids until I had kids. And then I just really enjoyed it because they’re so fun and creative and cool. You can do fun things with them. When you’re shooting adults, you’re constantly telling them what to do or at least directing them. You can’t do that with kids all the time, so they surprise me in a different way than anybody else can. I really love what they do, because they don’t try to do it. They just do it.

You’ve shot photos of your own children as well. Can you describe that experience?

Tons, yes. They’ve been an amazing inspiration for me over the years. I’ve never shot them so much that they hated it. I’ve never shot them so much that they hated it. I only shoot them when I have a really super great editorial idea or something. It’s not like I drag them out every second of every day and take pictures of them. I shoot them when it’s important and I have a cool idea. I want them to be part of it. And luckily I have beautiful children that are really perfect for my ideas.

         Rohm, Cleo’s son, as photographed by Cleo
        Haven, Cleo’s son, as photographed by Cleo

Are they interested in pursuing art?

Rohm — not too much. He’s super smart in math. Haven is a really good artist but he doesn’t notice it yet. But he’s really good. He can paint and draw really well, and he can pick something up and just paint or draw exactly what he sees. I feel like he has the creative gene and Rohm has the fashion gene. He loves fashion and buying clothes on eBay; I think he got that from me. He also shops on Mercari and Depop and all that. He likes the younger websites. It’s very cool to see.  

I also noticed that you have shot a lot of work in both staged settings and in natural landscapes. Is there one that you prefer over the other as a photographer?

Not at all! I like them both. I like really finished sets and an open field. I have a whole folder of inspiration called “in the grass.” I like both, really. I enjoy natural light and studio light. I like mixing them.

I think I would be really bored if I did just one thing.

With landscape ones, the location is always the inspiration. Whether it’s the beach or the woods or a field, I’ll just drive by and I’ll be like, “oh my god that’s so beautiful.” Also, the color — like now when the woods are really bare — I love that. I love that monochromatic vibe and that endless palette of warm colors. I think it’s so crazy beautiful.  And beaches — they’re so flat and so wide like and have that expanse of sky — like I can see a picture happening before I even take it. So with any more natural shoot, it’s really the location that’s so inspiring. With studio, I think it’s the facility of the studio and the subject matter that is so important. The graphicness of the picture is also inspiring.

It’s also easy to kind of manipulate anything now because of post-production. I don’t do crazy crazy retouching but sometimes I’ll put animals into a location or I’ll do that in the studio, too. There is a little bit of fantasy that I can bring. Not in every image, obviously, but the ones with the really large animals and the girls that are small or the ones with the owls in the studio that are bigger than the girls. I love doing that in the studio, but I would do that outside as well. So it doesn’t matter if it’s inside or on location or studio.

I manipulate images to bring them into my world.

And I don’t have a problem switching over. I could shoot studio one day, location the next day. Inspiration can come from the clothes, the person, the location. It doesn’t matter to me at all. It’s like, really good photographers — they just find it and they make it happen. I’m not really ever struggling to find something. I just find it. Whether you find the light or have a fantastic model; you find the inspiration, no matter where you are.

Do you shoot mainly digital or do you do film photography as well?

I used to shoot all film but now I shoot mostly all digital. So sad, I know. I see my little Leica sitting up there on the desk and I have an eight by 10 in the garage. Honestly, I have to say I like shooting digital because I like that I don’t have to send it off to the lab and wait for it to come back. It’s nice. Like I just shot Sunday, and today’s Tuesday, and I’m already sitting down and retouching and editing pictures. So the speed is really nice. 

I know you currently live in the Hudson Valley. Where were you living beforehand? 

I was living between New York City and Paris. 

And what brought you up here?

Kids, honestly. And schools and stuff like that. 

How do you feel like moving to the Hudson Valley has influenced you either as an artist or as just an individual?

I shoot a lot more location, because it’s right outside my front door. So I’ll be like: let’s go over here, I saw this really great tree. Sometimes it is just a tree, but it’s inspiring. And it’s really funny because nobody asks for permits here. They’re just like, sure you can come into my private orchard. No one ever bothers you. You can go climb a crazy tree and they’re not going to kick you out or arrest you. But in Central Park, they’re like, “you can’t climb that tree!” And then suddenly there are like six policemen there. So there’s a certain kind of weird freedom living in the country. Nobody bothers you. 

More artistic freedom to a degree?

No, it’s just different. Creators create no matter what!

Is there anything you miss about living in the city as an artist?

Good delivery services for all different kinds of food! I really do miss that. As an artist, I miss the museums. And I miss my people in the city —  they’re my creative people, and I only have like a small handful of them up here. 

What are your goals for your future, personally and or professionally?

Just to continue working on the level that I’ve been working on. And I’d like to go back to Paris a little bit here and there and do more jobs now that the kids are bigger. And to get a book published! I’ve been published in a lot of books, but none of them are mine. 

Is that a goal you’ve had for a while?

Yes, I have one that’s in the PDF stage and ready to go, but I haven’t approached any publishers.

And is there anything you wish you could tell yourself back when you were first starting out in this field?

Stay away from the dodgy boyfriend! And work your ass off, which is what I did. I worked so hard. I remember being really young, on a plane going to Kenya when I was 26. And this guy was like: “how old are you? Are you in college or something?” And I was like, “um, no, I’m 26!” And I remember another creative director telling me that I’d done a lot in my young life. And I was like, have I? But my advice would be: be super positive, work really hard, and never doubt yourself. I would totally tell myself that.

What are some of your favorite local businesses or places to visit in the Hudson Valley?

I like Le Shag, because Jen works there. I like her whole vibe and environment. I like my friend Kat’s store, Rivermint Finery, because she has excellent taste. She’s the coolest lady. I like Market St., it’s yummy. I like taking the kids skiing at all like the local mountains. I like all the farms and the really pretty countryside. Recently I’ve been doing little day trips to different towns with my friend Lawrie Bird. We’ll do a day trip to Hudson… oh, you know what I really love there? There’s this giant, antique mall building. Have you ever been there?

I think I know what you’re talking about! But I don’t think I’ve ever been inside.

You have to go, it’s crazy. I’ve never seen so many antiques and inspiring objects in my entire life. There’s also this really cute bakery in Hudson called Nine Cakes and they have the best macarons ever. Almost better than France, I have to say. They’re delicious. It’s at the top of Warren Street. Although Bread Alone has pretty good macarons too. I also really enjoy Le Perche and the restaurant at The Maker Hotel.

I like all the horses that are around, and the farms. I don’t love the cold up here, but I do love taking my kids to all the local mountains for snowboarding. And I do love the woods when they’re all monochromatic in the wintertime. I like looking out my window and seeing a flock of turkeys. Right now I’m just looking at two deer, but I really like the turkeys, and I wish that people wouldn’t shoot them because I think they’re really funny.

What are some of your favorite places to shoot in the Hudson Valley?

I like Burger Hill in Rhinebeck a lot, as well as Poet’s Walk. And there’s another park that I shot at pretty close to our house. But it doesn’t even have to be a place with a name. It can just be any street or anything. But I haven’t really shot in any of the mansions up here which are equally as cool. But just the woods and even the empty roads I think are super cool. There’s an orchard that ends up being in the background of a lot of my pictures and some fields that are really close to my house that I think are really pretty. And of course, I’ve turned my whole entire house into a studio.

Ok, last question! If you have one; what is your personal go-to hair routine for your average day? What do you like to do?

I use this really great smelling shampoo. It’s called Tigi and it’s really fantastic. I use their shampoo and conditioner and then blow dry my hair and then I straighten it with a straightening iron. And then the best thing that I put in it is Deepshine Oil by Rusk. And I color my hair a lot more frequently because it’s getting really gray. And I know all this stuff about my hair because of Stephen! And then every couple of months Stephen (my man) will put highlights in my hair. 

That’s a big perk!

Stephen is like, “you have $300 hair, by the way.” I have to say, this is a little bonus of having a hairdresser man: I went on a shoot and the model was like “your hair is so striking and so beautiful, and people notice you when you walk into a place just because of your hair.” I honestly have never heard anybody say that because I don’t really think about it often since I’m the one behind the camera. But the fact that she said that cracks me up. I just thought it was the funniest thing because I feel like I’m not a super high-maintenance kind of woman. I’m a more “I can wait for months to get like my hair trimmed” kind of woman. But I’ve always been fortunate enough that the people I work with offer to cut my hair, because I don’t go into the salon so frequently. Just having people who are around, you know, take care of me.