Artist Shop Spotlight: Jay Fleck

Jay Fleck may have never found his talent in illustration had it not been for his competitive spirit. Driven to win a challenge after discovering Threadless, he honed his technique until finally achieving victory. Today, his art – inspired by animals, nature, the whimsical, and the cute – has been printed over 20 times at Threadless, helping Jay become a full-time designer and illustrator. Most recently, he’s added Threadless Artist Shop owner to his resume, where his work is available on t-shirts, wall art, and phone cases. Read on to learn more about Jay, his work, and his latest project: a children’s book!


Hi, Jay! Welcome to Artist Shops. Why don’t you tell us a little bit about yourself?

Meet Jay!

I live in Shorewood, IL a suburb about an hour south of Chicago. I have a wife, two children, and the most loyal dog in the history of the universe, a weimaraner named Lily.

What has your personal journey as an artist been like?

Believe it or not, I got into illustration because of Threadless. I started submitting designs maybe ten years or so ago.  I never thought it would lead to a career or anything long-term; I thought I’d submit once or twice and then move on.  But I got addicted, and I wanted to win. I kept submitting and improving and learning new things, and then I experienced the sweet taste of victory!  And now I’m lucky enough to have a career in illustration. Thanks Threadless!

Shop “Big Mama” by Jay Fleck

Your work has such a whimsical, lighthearted quality to it. How did this particular style come to be?

When I first started, I wasn’t at all into cutesiness or whimsy. I worked mostly with simple shapes and geometric animals, and wasn’t interested in characters and personality.  As time passed, I became influenced by what other artists were doing. I’d see things that were cute and they’d bring a smile to my face, and I thought, why not? I started drawing animals in a more cartoony style; I think one of my first attempts was a design called “Hi!”. I still had to give it some edge; it’s a penguin about to be eaten by shark. I wasn’t quite ready for full-on cute just yet.

Shop “I Brought You These Flowers” by Jay Fleck

It seems animals play a large role in your work. Why do you find nature and its many creatures to be such a large influence for your work?

I love animals, and would venture to say that most people have some interest in animals. The sheer variety; different sizes and shapes, behavior and personality –  it’s pretty amazing and something we should all appreciate.  And you can use the connection that people have with animals and anthropomorphism to express human feelings and ideas; an elephant being a surrogate mother to baby chicks, a giraffe presenting a bouquet of flowers, etc.  And with animals, there’s a limitless palette of colors and shapes available to work with.

Shop “Fox” by Jay Fleck

What do you do to keep your imagination fresh and open?

I’m always looking for inspiration.  If I’m walking down the street or I’m shopping at a store I’m on the lookout. I like having multiple concepts in mind that I could work on at a moment’s notice; I don’t like the feeling of not knowing what I should do next or forcing myself to have to sit and brainstorm. I like having a full library of existing ideas at the ready. I write a lot down and start projects in Illustrator that are just some pieces of inspiration and ideas. Then when I have time, I go back and work on those projects.

Shop “My Red Bike” by Jay Fleck

Color and shape are two tactics that play largely into your work. How do you approach these elements, and why are you drawn to them?

I like simple shapes and contrasting colors. Why over-complicate things unnecessarily? I don’t want clutter, I want a nice color palette and clean composition that will attract someone’s eye with the focus kept on the main subject. I don’t want keep adding to an image just for the sake of complexity.

Shop “Owl 2.0” by Jay Fleck

What do you find to be the most rewarding part of being an artist, and what is the most challenging?

I’m happy that people have any sort of interest in my work. Getting an email from someone across the globe, someone buying a product, or even just a like on my Facebook page – I find it all pretty amazing. But it can be a challenge to come up with new ideas and new art, especially with that added pressure that some people like what I do and may have certain expectations. I don’t want to let people down with sub-par work, but at the same time I can’t take it all too seriously.

Shop “Dinner for 2” by Jay Fleck

You’ve got two young children. What do you hope your being an artist instills in them?

I think of artists as open-minded, progressive, able to work and focus as individuals, and create something unique. I want my children to have that mindset: be individuals and be themselves, but at the same time be open and inviting to other people and their ideas.

Shop “Scourge of the Arctic” by Jay Fleck

Speaking of kids, you’re working on a children’s book. What’s it about?

I’m writing and illustrating a story about an elephant falling in love with a tank. I’m also illustrating three other books for different authors. It’s fun but also very challenging; much different from creating single illustrations.

Shop “The Big One” by Jay Fleck

How has this new challenge of creating a book expanded your creativity as an artist?

My illustrations have always been standalone, individual works. I don’t reuse characters or tell a larger story through multiple pieces. Creating a single image with characters that are drawn in a single pose is much easier than creating a character that is used across pages, doing something different on every page. Drawing an elephant at a tea party holding up a pot of tea with his trunk is easy enough. But putting that same elephant, with his short legs and stubby arms, on a bike? Maybe that requires going back and making changes to the elephant in the tea party scene, so he also fits on the bike. Every page can have an affect on prior pages; I’m never quite done.

Shop “I’ll Be Your Tree” by Jay Fleck

When you’re not working on your art, what are you up to?

I like to jog, go for walks, and spend time outside. I like nice restaurants with good food, but I’m so far out of the city right now that it’s not always feasible.

Shop “Float On” by Jay Fleck

What are you the most excited about in the coming months?

I’m excited about finishing up work on my books and having them released. Then maybe I’ll have a bit more time to work on new projects; maybe write more?

Check out Jay’s Artist Shop here!

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Shawn Gauthier

Content Manager & Writer at Threadless. Into the usual stuff like words and music and internet animals.