Ollie Wootton

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Cartoon & Humour

Street Art & Mural

Colorful roller rink with skaters and people eating pizza by Ollie Wootton

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Comedian Jonah Eggleston on stage with colorful curtains, artwork by Ollie Wootton

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Colorful abstract figure with patchwork dress holding a cocktail glass 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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Colorful carnival tent with star top and moon phases, illustration by Ollie Wootton

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Roller skater drawn to heartbreak songs and mod culture.

Skate culture, animation and mod aesthetics inform a colourful and distinctive visual language.

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 colours and hand-painted textures,” says Ollie.