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Ollie Wootton

Ollie Wootton - United States based illustrator

Quirkiness and oddball humor abound in the work of Chicago-based illustrator and animator Ollie Wooton, yet there’s often a vein of deeper feeling too, giving the imagery poignancy and relevance too. This, coupled with the tactile qualities she brings through her textured brushwork, gives Ollie’s art a rawness and immediacy that makes the eye linger, drawing you closer to the work.
Trained in comedy filmmaking under a degree partnership between at DePaul University and Chicago’s famous Second City improv house, Ollie is an animator and a standup comedian. However, a desire to create and a tendency to draw constantly saw her veer towards illustration as a profession. She’s held a regular cartoonist slot with the New Yorker magazine and worked for an eclectic range of brands in everything from skin care to skateboarding. Ollie is an avid roller skater who’s inspired by skatepark culture and animation such as Smiling Friends, BoJack Horseman and Bob’s Burgers. She loves Matt Maltese, Elliott Smith and any musician who sings about heartbreak. Clients love the insight she brings to projects, her great communication and the way she offers practical creative solutions with each brief she tackles. Lastly, she’s a huge fan of the 1960s mod aesthetic, which you might also detect in her work.

Approach

Ollie uses gouache and collage techniques alongside Adobe software and Procreate. Whether using natural media or digital tools, she chooses brushes that give her work a handmade feel. Gouache is always preferred but digital tools are there for the practicality of client revisions and prompt delivery.

Key software

Adobe Creative Suite and Procreate.

Style

“I would describe my style as playful and otherworldly paired with a sharp, observant edge. I use lots of bright colors and hand-painted textures,” says Ollie.

Languages

English and German.

Client list

Ollie’s clients include The New Yorker, Ulta Beauty, Clean it Zero, Jack Black, BRAV Magazin, Unabridged Books, Streetslider, Butter London and more.
Colorful abstract faces with bright patterns by Ollie Wootton
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"Cocinella Spring"
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Illustration of children dancing in a circle under a colorful disco ball by Ollie Wootton
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Illustration of woman in vintage dress from Beware of Pity by Ollie Wootton
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Self Portrait
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Illustration of person trying to clean grease spot, by Ollie Wootton
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Illustration of a woman hugging a giant black and white cat by Ollie Wootton
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Sniff
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Comic panels showing girl with banana and sitting by statue, by Ollie Wootton
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Cartoon of people in a meeting complaining about preferring an email by Ollie Wootton
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Cartoon showing baby shoes and funny for sale signs by Ollie Wootton
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Black and white illustration of a couple struggling over covers by Ollie Wootton
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Colorful roller rink with skaters and people eating pizza by Ollie Wootton
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Black and white drawing of five people with text about coffee for breakfast by Ollie Wootton
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Black and white drawing of alien abduction with person floating to UFO by Ollie Wootton
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Illustration of books with faces hugging each other, drawing by Ollie Wootton
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50 First Jokes 2026 event poster with cartoon cake and candles by Ollie Wootton
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Illustration of two pencils interacting at a mirror by Ollie Wootton
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Colorful abstract figure with patchwork dress holding a cocktail glass by Ollie Wootton
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Cartoon woman with blue hair carrying books in Unabridged Books mural by Ollie Wootton
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Cartoon woman flying holding a blue dog by Ollie Wootton
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Comedian Jonah Eggleston on stage with colorful curtains, artwork by Ollie Wootton
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Indie Bookstore Day window mural featuring cartoon character by Ollie Wootton
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Cartoon character reading book in bookstore window by Ollie Wootton
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Colorful reading character mural on bookstore window by Ollie Wootton
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