Behind every beautifully painted woman, there’s another woman. In a society that treasures stunning women, Cindy Press looks to expose something deeper. She incorporates her own experience with relationships, love, anguish and personal battles into her artwork, creating profound yet edgy paintings. The Philadelphia native spent much of her professional career in fashion illustration but has since left that field to pursue her true dream in art. She has been named one of the top 100 American best sellers by You can purchase her art online at

Please tell me a little bit about yourself and your art journey. When did you first start to draw/paint? Did you always know that you wanted to be an artist?

There was never any choice for me. I’ve been making art in some form or fashion my entire life. When I was young, I used to come home from school every day and draw for hours. It’s the only thing I’ve ever wanted to do. When I decided to go to art college, my parents were afraid that I would become a “starving artist” so they told me I could go to an art college if I majored in a professional art instead of a fine art. I chose fashion illustration not realizing there aren’t really any jobs in that field! My career started in the fashion industry making art for clothing. I worked with the well-known artist from the 60’s, Peter Max, to help interpret his artwork on clothing, it was the 80’s and that trend was really big then.

Now I’ve come full circle, I gave up my career in fashion to be a stay at home mom and seriously picked up my paint brushes again five years ago. I’m now finally doing exactly what I’ve always wanted to do which was paint and draw every single day. My fashion illustration roots serve as the backbone for my work, but the more important focus is about the psychological complexity of women making it all much more personal for me.

Cindy Press Art
Cindy Press Art

Your paintings are incredibly realistic. How long did it take you to master this craft?

I don’t think about making my paintings realistic on purpose, I just paint what I see, and they turn out that way. The human figure has always been the most challenging and interesting to me, so I never lose interest in my subject.

I think the best thing you can do as an artist is practice and work every single day! The more I work, the more I learn and see differently. I don’t think I’ve mastered my craft yet; it’s always changing.

Right now I’m trying to loosen up a bit and get less “realistic,” that’s more difficult for me, and it pushes me out of my comfort zone.

Cindy Press Art
Cindy Press Art

Most of your paintings are of women. What inspires you to pain them? What is your favorite part about the art that you create? What does your artwork aim to say?

I mentioned that I started out studying fashion illustration which I truly still love. So when I started painting again, that was my focus. As I began to paint though I noticed a shift in my perspective, it wasn’t at all the fashion that was important to me anymore, but the mood the expression or the pose represents to me. I am inspired by fashion photography and find my poses from that world but as I start to paint the piece starts to take on new meaning. I consider a history of experiences, my life, my relationships, the anguish, and personal conflicts come into play. There is so much more behind a person’s appearance.

I am trying to connect with the viewer on a deeper level with my work hopefully touching on an experience they can relate to as well. That is my favorite part of making my art when it touches someone in a way that words cannot.

Cindy Press Art
Cindy Press Art

As an artist did you have any struggles, and if so how did you overcome them?

Oh, there are so many struggles as an artist I don’t know where to begin! I think figuring out how to handle the gallery issue is one of the hardest.

It’s a different world, and an artist can no longer walk into a gallery with an outstanding portfolio and hope to be represented by that gallery. If you do that today, it’s a sure way to get them to NOT want to represent you. I’ve been told I have to network to find galleries which is exhausting!

There’s a tremendous amount of research that has to be done to find a gallery that’s a good fit, then once you’ve done that you have to actually find people that know the players in that gallery? It’s impossible, and no other industry in the world operates that way. Luckily we live in a world of technology which allows us to reach collectors in other ways besides the traditional gallery, so I’ve tried not to get caught up in where my work is showing anymore and focus my energy into making it rather than networking to get into the right gallery.

Cindy Press Art
Cindy Press Art

What has been the happiest moment in your career so far? The saddest moment?

The happiest moment was last spring when I sold five paintings to one collector! Nothing makes me happier than to pour my heart and soul into a painting and have someone want to actually pay for it but when a collector purchases more than one piece, well what else can you ask for as an artist? I have many collectors who also have purchased more than one or two of my pieces, and that is also the most amazing feeling!

Someone actually likes my work enough to purchase more than one painting? Five at once was just really exciting! I am so happy doing what I love every day I don’t really have any sad moments.

But I guess if I had to pick one it would be the only painting I ever lost. It was purchased by a collector in Indonesia, and it arrived at the post office there, but I was told it was never picked up. It was supposed to be returned to me, but I never got it back. I’ve learned my lesson, and from now on I only ship through DHL to that part of the world.

Cindy Press Art
Cindy Press Art

What are you most afraid of right now?

What I’m most afraid of right now, and always, is losing my eyesight. My mother was legally blind when she died five years ago due to macular degeneration. I watched her life deteriorate along with her eyesight over ten years, and now that’s my biggest fear. The bad news is that macular degeneration is hereditary, but the good news is if you catch it early enough it can be reversed. I might be more scared of never being able to paint again because of it than being blind.

Cindy Press Art Painting Illustration Women Models Artists The White Room Gallery Hamptons Human Figure
Cindy Press Art

If you could give one piece of advice to a large group of aspiring artists, what would it be?

Work as much as possible is always my advice but that doesn’t just mean work at your art. I work seven days a week! Being an artist isn’t just about making the art anymore. You have to market yourself which means creating your website and maintaining it. You have to get your work on social media, knowing when the best time to post is and engaging with your followers (that can be a full-time job in itself). You have to be a shipping department, that means figuring out the best shipping rates to send your work all over the world. It also includes ordering all the shipping supplies and knowing how to pack your artwork properly. You have to be a photographer if you aren’t one already, and learn how to take proper photos of your work. You have to be willing and happy to speak to and negotiate with collectors about your work. You have to become your own lawyer if you can’t afford one and read through contracts when licensing deals and galleries come along. You should be willing to take commissions that can sometimes feel much more like work than anything creative.

After all that you need to find the time to still make your art. You have to be willing to do everything in order to do that one thing you really love.

You can see Cindy’s work in the Hamptons at The White Room Gallery.



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