Fashion Illustrator & Entrepreneur Deanna First Talks Sketching, Style & More

“I view art and fashion as one……”

Fashion and art have always had a dynamic relationship that is constantly evolving. Exploring and celebrating the connection between the two mediums, Deanna First is a passionate New York-based illustrator specializing in hand-drawn fashion and beauty artwork. Sketching through a combination of pencil, marker, watercolor, and digital editing, Deanna is known for creating fluidity and movement in each of her portraits.

Turning her talent into a thriving business, Deanna commissions individually tailored portraits for private clients as well as emerging and established global brands. She regularly creates customized, fashion illustration drawings at galas and events, as well as for editorials, menus, invitations, cosmetic packages, book covers and more.

Deanna’s sharp eye for capturing the essence of her muses has garnered her a long list of luxury clients including Valentino, Dior, Tiffany &. Co., Estée Lauder, L’Oréal, Jimmy Choo, Ralph Lauren, Diane von Furstenberg, Cipriani and more. Her work has also been featured in leading fashion publications such as Vogue, Daily Front Row and Harper’s Bazaar.

“I knew I wanted to be an artist since pre-school. To be living my passion as a full-time artist in NYC is still surreal,” says Deanna, “I am beyond blessed and thankful to have found my purpose bringing joy to others through my work.”

Loop Magazine recently caught up with Deanna during New York Fashion Week where she chatted about her sketching process, her dream collaborations and more. Check out the exclusive interview below. 

When did you decide to pursue illustrating full-time?  Back in 2016, I believe. I originally studied fashion design with a specialty in eveningwear. I worked at Ralph Lauren and J.Crew before pivoting to art. I was not drawing at my corporate jobs and knew I needed to take a different path that aligned with my gifts. I’ve wanted to be an artist since pre-school so I always knew my purpose on earth was linked to art. I’m just so thrilled to be living out my passion and excited for the opportunities to come. You’ve collaborated with numerous iconic fashion and luxury brands like Hermès, Valentino, and Dior. What have these experiences taught you about the intersection of art and fashion?  I view art and fashion as one. My artistic projects are often inspired by fashion and top luxury fashion houses that partner with artists on print design and concepts to bring life to their visions. How do you decide which events / projects to accept?  I accept projects I feel are on brand for me and align with the direction my career is going. There has to be mutual compatibility to proceed. When brands and companies that are known for their attention to detail and high standards reach out, joining forces to create something beautiful and a unique client experience just makes sense.

How long, on average, does it take you to complete a sketch?

I have it down to about four minutes for a live sketch. My friend Azia recently told me she thinks I’m down to three minutes or less when she attended my recent LA event. If an attendee is wearing an intricate print or design. that can add additional time versus a single-colored look. I joke that I knock a minute off every year, so pretty soon I’ll be down to seconds. 

What is it like creating customized, hand-drawn fashion illustrations for high-profile events such as galas?

It brings me so much joy to capture the essence and aura of the guests I’m sketching. Seeing people light up when I pass off their illustrations is the best feeling. I get chills just thinking about it. Knowing my art is circulating in so many homes across the globe and a tangible memory for guests is surreal. 

Your work has been featured in prominent publications like Vogue and Harper’s Bazaar. How does this recognition impact your artistic journey? 

I am flattered when top publications notice my work, but it has not changed me or my work. I still put the same effort and quality into every piece I create regardless of the publications that happen to mention me.

How do you tailor your commissions for private clients or weddings, versus emerging and established global brands? 

My focus aligns most with corporate clients in the luxury market. Once in a while I will sketch at a wedding or private event in the Hamptons, but the majority are global brands.

What is your favorite memory from an event you drew at? 

I loved sketching guests at The Plaza Hotel’s Met Gala Event that honored Karl Lagerfeld. I captured attendees coming down the iconic Plaza staircase. It was so magical and a way to merge my love for evening wear with my art. Traveling with Tiffany & Co. across the Northeast and being an artist in residence at their NYC Flagship was also a high for me in my career thus far.

Do you travel for events or do you primarily stay in New York? 

I travel often for work. As we speak, I am on a flight back from Hotel Bel-Air where I teamed up with Global Travel Collection. I do travel world-wide but also book events in the Hamptons, Greenwich, CT and surrounding areas outside of NYC. My home base has been NYC for the past 12 years though.

How do you prepare for a crazy day of events?

To be honest, during very crazy days for events I grab food on the go or I try to pack a protein or meal bar. I’ve never been much of a cook. After a day of several back-to-back events, I unwind by taking a hot bath, saging my apartment, and doing a guided meditation. I also have a light oracle deck I pull from for guidance and to regroup after being surrounded by so many different energies and people throughout the day.

What do you wish people knew about you or your work?

I wish people knew just how passionate I am about what I do. I truly feel that my career as an artist is linked to my soul mission on earth. Creating and bringing new ideas to life brings me so much joy. I feel that I have just scraped the surface in my career and can’t even fathom the opportunities that await me if I continue to let go of fear.

What new themes or styles are you interested in exploring in the future?

I would like to gravitate towards making my live sketches a bit more “looser.” My line quality, use of my glamorous touch of sparkles, pearls, and gold/silver paint and how I capture people’s aura and essence is what sets me apart from other artists. My style will shift organically and throughout my career so I’m excited to see how it unfolds and develops throughout the years to come!

Are there any dream collaborations or projects you would like to work on?

There is one in particular, but I don’t want to jinx it by speaking about it just yet since it feels so close to happening. I would love to collaborate with Chanel, Oscar de la Renta, Prada and be on the actual red carpet for events at the Oscars, The Met Gala, and the Grammys during award seasons. I envision my own sketching station where select celebrities stop by for a brief sketch and chat session with me.

I am interested in branching off and doing more brand partnerships where my artwork is on products for either a limited-run artist collaboration collection or even print designs for a runway collection. My artwork incorporated into luxury store windows as the backdrops would also be in alignment with where I see my career evolving. I see more artist-in-residence opportunities in my future as well with brands that I feel are compatible. Live sketching at an actual runway show during Paris Fashion Week, New York Fashion Week, or globally is also on my radar.

How do you see your work evolving in the next few years, especially with the advancements in digital art? 

Each year my style evolves. I grow as an artist and become more confident with every line I draw. I’m old school and use pen and paper. Sometimes I use a mix of digital coloring to give more depth to artwork and play around with different layouts. I like to stick with what feels natural to me. I even have a paper planner, notebook and prefer a paper book over a digital book any day. 

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