Drawn to It

Fashion illustrator Dallas Shaw—who counts Chanel, Ralph Lauren and Christian Louboutin as clients—finds inspiration in Florida.

Former Sunshine State resident and nationally recognized style influencer Dallas Shaw is partnering with the Four Seasons Resort Orlando at Walt Disney World Resort for an exclusive line of drawings.

By Nila Do Simon
Portrait By Alison Conklin

She’s the go-to fashion illustrator for brands like Kate Spade, Marissa Webb and Adam Lippes. Her artwork has graced the official tote bags of Mercedes-Benz Fashion Week, and last year she became a published author with best-seller The Way She Wears It: The Ultimate Insider’s Guide to Revealing Your Personal Style. Dallas Shaw’s work has become synonymous with style and fashion, but for the artist—who splits her time between Nashville, Tennessee, and Wilmington, Delaware—Florida is where her career found new heights.

After graduating with a degree in illustration, the Pennsylvania native accepted a position as an animator for Walt Disney World in Orlando, Florida, a job she had dreamed about since childhood. She arrived at Disney in the early 2000s when the company was transitioning from hand-drawn productions to computer animation. At a crossroads in deciding whether she should remain at her dream company as a computer-based designer or stay true to her roots as a hand-drawn illustrator, Shaw eventually followed her heart.

She married her love of fashion with her bespoke drawings and paintings, creating an oeuvre of chic yet whimsical illustrations depicting stylish girls complete with tightly wrapped chignons or T-strap stilettos. Her career has since ballooned into creating custom designs for beauty brands such as Tata Harper, La Prairie and Glossybox. This spring, Shaw unveils her latest designs of promotional materials for the Four Seasons Resort Orlando at Walt Disney World Resort—a collaboration she says takes her back to her Central Florida career roots.

What are your must-have tools, and how has that list changed as the industry has become more digitized?
My “office” is pretty much on me at all times. I always carry a sketchbook, a mix of pencils, watercolor and ink. I’m a lot of things, but I’m not a graphic designer. The only digital tool we use is a scanner.

When we’re doing visual consulting, we use things like corkboards and pin boards to move images around. I imagine it’s really funny for someone listening in on one of our visual meetings to hear us have deep discussions about things like palettes. Once, I even had an hourlong conversation about a bike basket! I asked questions like, “Would this character use this type of basket?”

Shaw’s illustration from her 2017 book, The Way She Wears It: The Ultimate Insider’s Guide to Revealing Your Personal Style.

What about the Four Seasons Resort Orlando falls in line with your aesthetic and brand?
When the Four Seasons approached me with this collaboration idea, I instantly wanted to say yes. I felt like it was a chance to go full circle with my career because I previously lived in Orlando for five years. On top of that, the property wanted to create illustrations that were tailored to this resort and its identity as a luxury property that remains laid-back without dropping an ounce of elegance.

What was your approach to creating the bespoke illustrations for the Four Seasons property?
The company brought me down to stay at the resort for a weekend to get to know the property and see all the things I would be drawing and painting. I wandered around and took notes and photos of everything. Despite having lived in Florida, this felt like a completely new experience—like I was nowhere near the Florida that was familiar to me.

As I walked around the property, I put together a list of what I call “moments,” which are basically these “wow, it’s beautiful” moments that stop you in your tracks, like the chandelier in the entryway or the path lined with palm trees. Unbeknownst to me, the hotel’s team did the same thing, and it turns out our lists were exactly the same. I love when people totally get it and really connect with my aesthetic.

Shaw’s illustration of the Four Seasons Resort Orlando’s signature entryway chandelier, which is made of 30,000 crystal components.

How is designing and illustrating for a hospitality brand different from designing and illustrating for a fashion brand?
With fashion brands, we’re always thinking about what will be trending next year or what color palettes will transition well through seasons. With hospitality brands, I’m thinking more about how certain designs fit in with the overall marketing message. You have to make the design more general and make it about the resort rather than a specific trend or topic, which always turns out to be a fun challenge.

You seem like the ultimate girl’s girl. How have you managed to maintain such a strong female-centric brand?
I’m proud to say that right now we have an all-female team. We never consciously sought to only hire women, but it doesn’t surprise me that it’s how things worked out. I got my start with other women helping me, and my career just took off from there. Today, a lot of college girls come to me for internships, which is something I’m happy to pave the way for.

How have you managed to balance the workload that comes with being the head of your company while illustrating full time?
I’m the only illustrator and artist in the company; I would never pass the illustrations off to anyone else, especially because companies hire me for my signature. I think it’s important to practice your craft. So ideally for a few hours a day, I shut myself away from the world—and my email—and just draw.

Shaw’s illustration for Adam Lippes.

What advice would you give to aspiring entrepreneurs?
When I started working at Disney, the company was transitioning to focus more on computer animation, but I was a 2-D illustrator. That’s where my heart is. So I left Disney after a few years and took a teaching job in Kissimmee. I worked in the classroom from 7 a.m. to 2 p.m. and worked on building my business from 2 p.m. to midnight.

I don’t tell anyone to just give it a shot without some heavy thinking. You have to learn how to make money, especially in the creative field. I knew I wanted to work in art and fashion, and later I figured out I could use my fashion illustrations to work in lifestyle.

What can we expect from you in the near future?
I’m excited to introduce my new company, Faerie, which will include my artwork and illustrations on paper products. Much of my work is done in collaboration with others, whether it’s another company or brand. With Faerie, I’m able to produce pieces that come from me and me alone. It’s my way of creating products that have me saying, “These are the types of pieces I’d buy.” I even love the name: Faerie is pronounced like “fairy.” It feels editorial but still magical.

We couldn’t finish the interview without asking: How did you get your name, Dallas?
I wish I had an epic story, but it’s pretty simple: My mom heard the name growing up and really liked it. She thought it was a boy’s name at first, but then she heard of a girl with that name and thought it would work for me. Thankfully it has.

Shaw’s illustration from her 2017 book, The Way She Wears It: The Ultimate Insider’s Guide to Revealing Your Personal Style.

This article originally appeared in the Spring 2018 Issue.