How Ashley Longshore Became The Fashion World’s Go-To Artist

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As the fashion world’s go-to artist, Ashley Longshore has become synonymous with work that’s provocative, bold, and hilarious. And she makes no apologies!  The Daily recently sat down with her to unearth how she got started, why social media was instrumental in her success, and what she’d still love to do. 

When did you know that you had talent?
I realized I could paint at 19. I didn’t know if I was ever gonna make a million dollars or find the love of my life, but I have this now, and I want it all the time. How can I sell these? How can I make this a career? Because that is the dream, that is the American dream, to be financially independent and to do what you love, right? I found this way of expressing myself that brought me joy and a love I’d never felt before. I was definitely born an artist, and I just love creativity. I went on a rant the other day about why New York is great. It ain’t hedge funds or lawyers. It’s theater, it’s fashion, it’s why people come here—food, art, museums, music.… I’ve never felt more punk than I do right now.

Why’s that?
I am financially independent. I feel as though I can give my manicured middle finger with the 10-carat diamond I bought myself to put out to the galleries that told me I wasn’t marketable, and say, “F**k you guys.” I’m still gonna stand up for what I believe in. I’m still gonna stand up for those of us who are creative and nerds and bohemian and have souls and empathy, and we believe in capitalism, but on the level that when we become financially independent, we help our community, we don’t hoard it.

Was there anyone supportive of your talents when you were growing up?
My dad. I’m the woman I am because of my dad. In the beginning, he thought, because he’s Southern, too, you make your art, but then you go marry somebody that’s got a lot of money. I never felt like I needed that. And my dad raised me to stand up on my own two feet and be authentic. He was supportive of me.

Dolly Parton by Ashley Longshore

Tell us about the journey of people saying no to you.
When I first started, this was before social media and all of that had hit, it was a time in the art world when you needed to be someone connected to representation. Thankfully, I was lucky enough to pop my cherry at a time when those amazing things were happening in the world. But I’ll tell you what bothered me the most to begin with, which a lot of people don’t even know when they’re collecting art from galleries, is the galleries take 50 percent of the cut. In my opinion, 50 percent is an unreasonable percentage. Also, I’m an art collector, I try to buy directly from artists all the time, not to ask for a discount, but rather to know that 100 percent of that money is going to them.

When did you feel like things really took off for you?
Have they?

You’re doing very well!
When you’re in the eye of the hurricane, there’s so much happening. I felt like I’d made it the first time somebody paid money for a painting. Being able to celebrate little successes, like I’ve e-mailed 20 people and three people e-mailed me back. That’s really been the secret of how I’ve gotten to where I’ve gotten, and it’s about optimism and self-love.

What would make you feel like you have arrived now?
I would already have my foundation set up and have a space to showcase other artists. I feel like I would be further along with that. That’s what the long-term goal would be to have. I don’t have human children, so my legacy would be to have something like that. Also a jet. A yacht, you know?

DVF by Ashley Longshore

Do you think you would have the same career without social media?
No, absolutely not. I was born in a magical time to be a creative, and it’s an incredible time to be creative for that reason, because it’s free. Back in the day, it’s like, no, I can’t go spend $600 on postcards and $300 on stamps and mail this out to people. Instead, you go on social media, and it’s instant. I would finish a painting and put it on Instagram, boom, it’s sold in an hour. That’s incredible to be able to stay connected with people. I mean, now I feel like we’re battling the algorithms, because in the beginning, it’s like you could go take a leak, make a post, everybody sees it, and now they’re really showing you what they think you only want to see. It’s horrific. Still, when I talk to young artists, I say this is not the be all, end all, but it’s an incredible tool.

We remember you did a painting in the middle of Christian Siriano’s runway show a few years back.
I also did a big collab with Gucci. I’m a designer for Judith Leiber. I’ve designed about nine or 10 bags for them. I love Dee [Ocleppo Hilfiger]. She and Tommy [Hilfiger] have been good to me. They’re such nice people. They’re so pretty. I also had a massive exhibition at Bergdorf Goodman. I had my own café there. So look, fashion, creativity, they’ve been a huge part of what I do. But also, as a pop artist, I love all the stuff. I want the bags I want, the clothes I want, the couture. I have all these things. I love the idea that fashion can just let everybody see on the outside how I feel on the inside.

Have you ever had any controversies with people?
I have been completely misunderstood. Are you kidding me?

It’s interesting that you used the word “misunderstood.”
Completely misunderstood, misrepresented, absolutely. But I think, too, and I say this to artists all the time, if you’re going to put yourself out there, you have to know, especially if you’re dealing with the Internet, what a vile abyss of horrificness it can be. You better be able to look at yourself in the mirror
and tell yourself the reasons why you love yourself and why everything’s going to be okay, and to keep pushing forward. Especially being a woman. What do you do? You keep making art.

Nina Garcia by Ashley Longshore

Have you received great support from other women?
Huge.

That’s good to hear.
Ginormous. It’s funny how we are as humans, that we could have 20 people tell us that they love us, and one person says they don’t, and what do we do? We think about the one person who says they don’t. I have the most incredible collectors, unbelievable. I mean, like the schoolgirls who come by and see the art, who love it. I have incredible fans. Incredible fans.

What’s your creative process like?
Right now, I’m doing this whole series of Princess Diana paintings, and I’m using this transparent glitter over her face, as she looks really ethereal, and then I’m using heavy texture around the back. And it’s her, the iconic photographs of her and her crown looking around, and she almost looks like those paintings of Jesus. She’s just so captivating. I just see her as this radiant light that could have been, and how she just got sucked up by those royals. I remember that night when she died. I was in college, and it really affected me.

What’s next for you, and what do you want to do?
It can be quite nebulous about what can happen next, because the art is all sparked from lightning in a bottle, which can happen at any moment. Being in a city like New York, anything could happen. The phone could ring, and it could be anyone. I think I hit all my major goals by the time I was 40. Is there one thing in particular that I’m still burning to do? Designing a [theater] set. Wouldn’t that be awesome? Or for some random person to just give me $100 million. [Laughs] I’m happy to be honest with you. Though it’s stressful to be an entrepreneur right now. It’s stressful to run a team. It’s not an easy thing to do.

How would you like to be remembered?
As somebody who was joyful and inspired joy. That’s the best part of life, isn’t it?

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