How Daniel Winter Went From a Self-Taught Tattoo Artist to a Go-To For Celebrities

Courtesy of Daniel Winter | Getty / Illustrations by Keila Gonzalez
Courtesy of Daniel Winter | Getty / Illustrations by Keila Gonzalez
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Welcome to Big Break, where some of the most influential figures in the beauty industry reflect on the moments that made them — from the good to the bad and everything in between. Here, self-taught tattoo artist Daniel Winter (aka "Winter Stone") looks back at his whirlwind career with clients like Miley Cyrus, Chrissy Teigen, Sophie Turner, and more.

Daniel Winter got his first tattoo at 16 with his 12-year-old brother. It was a "W" on their feet to represent their last name. They used a needle, ink, and string.

"Growing up, my older brother was always around the tattoo scene, and a couple of his friends had a lot of tattoos, so my little brother and I decided to tattoo ourselves in the kitchen," Winter told POPSUGAR. "My mom came in the kitchen and was like, 'What are you guys doing?'"

Unlike some shoddy DIY tattoos that fade over time, it's still one of his thickest, most visible tattoos to this day.

Courtesy of Daniel Winter

Winter's first professional tattoo experience came two years after his first at 18 years old, when he got a Celtic cross on his back in honor of his grandma. At the time, Winter wasn't considering tattooing as a profession; he was on the path to becoming a freelance artist, but his medium was clothes and paintings.

He continued getting tattoos for another 10 years, and then it hit him: "I just had this dream to try it and see what happens," Winter said. He had always loved creating superfine line works of art, but instead of using pencils and pens, he wanted to give it a try with a tattoo gun.

"I had a few people tell me that I shouldn't be a tattoo artist, and that just lit a fire under me," Winter said. "I took that as a challenge and got a machine and just started." He was on a mission to prove naysayers — who, ironically, told him he wasn't a "good enough artist to be successful in the trade" — that he could do it.

Courtesy of Daniel Winter | Getty / Illustrations by Keila Gonzalez

The first few people to let the self-taught Winter tattoo them were his little brother and his best friend. He had practiced on a ton of different materials and was finally ready for the real deal — even though he was full of nerves and anxiety. "As soon as I put the needle in the skin and started to do my thing, I thought, 'This is going to be something,'" Winter said. "I just knew right away — I can't explain it. It was kind of like a gift was just sitting in my body dormant, waiting for this moment."

That day set the ball in motion. In 2011, he decided to "roll the dice" and open up a private studio with other artists — not tattooers, but designers and painters. "I wanted to break the mold and show people that you don't have to do things traditionally to become something," Winter said. Instagram was just starting up, and he was utilizing it as much as possible, and things "took off from there."

"When I picked up the machine for the first time and saw how naturally it came to me, I knew this was what I was going to do. I was all in. I never ever looked back, not once."

As a third-generation native of Beverly Hills, Winter grew up alongside A-listers his whole life — he went to Beverly High, after all — and it was through word of mouth that he landed his first four celebrity clients in 2016, all at once from the cast of Pretty Little Liars. They shared the work on Instagram, and the next opportunity followed immediately. "I got a text message from Miley Cyrus saying, 'Hey, I want to come in and get tattoos. I heard you do cool fine-line work,'" Winter said.

The next thing he knew, Winter was at Cyrus's house tattooing her Happy Hippie Foundation logo — the smiley face with the two H's for eyes — on her inner arm. "I don't know what I was thinking, but I let her tattoo it on me," Winter said. "And it's pretty funny — I mean, it's horrible, but it's funny."

Courtesy of Daniel Winter

Once he inked Cyrus, the celebrity requests started pouring in. Soon enough, his art was on Mandy Moore, Demi Lovato, Chrissy Teigen, Joe Jonas, Sophie Turner, and more. Now, it's hard to find a tattoo-loving celebrity in California whom Winter hasn't inked, but he likes to remind everyone that the celebrity clientele is only one percent of his total business. "The other 99 percent of my clientele, which is normal people, is what makes my business kind of go around," Winter said.

It's easy to spot Winter's tattoos on Instagram — they're incredibly clean and precise; a true work of art. He likes to look at artists like Matisse, Picasso, and Salvador Dali. "When you look at Picasso, his stuff is so simple, but it has such an impact," Winter said. "So I try to kind of mimic my style toward that minimalistic vibe."

But his main source of inspiration is his clients, and he prides himself on giving an extremely personal tattoo experience. "You come in, we sit down, we have a conversation, and we go over what you're thinking," Winter said. "Ninety-nine percent of the tattoos that people are getting in my studio are extremely meaningful."

Being completely self-taught, he can't give credit to any one mentor for helping him get to where he is; he was a "lone wolf" when he started out. "The tattoo industry 10 years ago was very different from what it is today," Winter said. "It was very, very strict in the sense where now it's more like artists giving tattoos instead of just picking a piece of flash off the wall."

Courtesy of Daniel Winter | Getty / Illustrations by Keila Gonzalez

That nontraditional entry into the tattoo industry is why he encourages people to follow their dreams, even if it means you have to "take an unconventional path." He said, "People think they have to do something a certain way and follow all the rules. For me, it's like, break the mold, be different, do something different — that's going to set you apart."

Looking back on his career, it's hard to pick one defining moment. "There are so many levels to success," Winter said. Right up there with the time he tattooed the rose on Lady Gaga's back to commemorate her Oscar nomination for "A Star Is Born" is the tattoo he gave his mom, who's also an artist. "That was a good feeling for me," Winter said.

He is nowhere near done furthering his art and still very much considers himself to be on the rise, but he's extremely proud of how far he's come. "When I picked up the machine for the first time and saw how naturally it came to me, I knew this was what I was going to do," Winter said. "I was all in. I never, ever looked back, not once."