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Sketching Her Way To Success

Behind the Scenes with Professional Illustrator Deanna First

For over a decade, Deanna First has seamlessly merged the worlds of fashion and art, creating a distinctive career as a professional illustrator.

“I’ve wanted to be an artist since preschool,” Deanna shares. “I even have a drawing I did when I was six of a girl by an easel saying, ‘My job will be an artist.’” That childhood dream, born in Ohio, has blossomed into a thriving career in New York City.

After moving to NYC, Deanna combined her love of fashion and illustration, briefly working in roles at Ralph Lauren and J.Crew but eventually ventured into entrepreneurship as a professional illustrator. Today, her art studio houses that childhood sketch as a reminder of her progress.

Deanna’s ability to bridge fashion and illustration is a testament to her artistic vision. “Fashion is more than clothing—it’s about capturing someone’s true essence on paper,” she explains. She seeks inspiration from global fashion weeks, red carpets, and the aura of her subjects.

Her preferred tools—microns (fine tipped markers) and Copic markers—offer the blendability of watercolors with more precise control, enabling her to create pieces that celebrate motion and femininity. “I’m incorporating more movement into my art, moving away from perfect lines,” she notes of her evolving style.

While her live sketches at galas, think The Met Gala, and high-profile events have garnered acclaim, Deanna’s creative process varies between personal and commissioned work. “Custom commissions involve capturing every detail of the client’s vision, while personal pieces allow for more freedom and therapeutic expression,” she says.

Memorable collaborations include stints as the Artist in Residence at Tiffany & Co. as well as The Plaza Hotel. If you’ve ever enjoyed a glass of bubbles at The Plaza, you’ll recognize her illustrations on the menu at the Champagne Bar.  

Deanna has worked with several notable west coast clients as well. “Working with The Beverly Hills Hotel and Hotel Bel-Air on holiday cards last year was a dream,” she beams. She looks forward to more world-wide collaborations in the coming year.

From fashion campaigns to people-watching, inspiration is everywhere for Deanna, though she remains focused inward. “I do my best work when I tune inward rather than looking outward,” she says.

She has collaborated with incredible brands such as Louis Vuitton, Dior, and Hermes, just to name a few and social media has played a pivotal role in connecting her with those iconic brands. “I’m so grateful for the power of social media—it’s connected me to clients throughout the world.”

Despite her fast-paced lifestyle—she once traveled between events in NYC, The Hamptons, and Boston in a single day—Deanna remains dedicated to her craft. “Sketching is a small part of my career,” she shares. “The rest involves marketing, content creation, and managing the business side of things.” But on the days she’s sketching in her studio, she can be found listening to meditative music or nature sounds and enjoying the company of her cat, Willow.

Her goals for 2025 are ambitious: sketching at the Oscars and Grammys, designing store windows and product packaging on a global scale, and manifesting collaborations with Oscar de la Renta and Chanel. But Deanna prefers to keep her upcoming projects under wraps until they’re finalized; a lesson learned from past experiences. “There’s something special about surprising people with an announcement.”

To learn more about Deanna, her beautiful illustrations, and the iconic brands she works with, follow her on Instagram @deanna_first.