About

We’re here for the mistakes.

Cheeky Pickleball began as a father-and-son project with one idea: the funniest moments in pickleball are the mistakes everyone recognizes.

So we worked with a professional illustrator to create a monkey with a pickleball problem. Each design pairs that monkey, mid-mistake, with a straight-faced dictionary definition. It’s a joke that only lands if you’ve played.

The first shirt is the Unforced Error Tee. It’s for anyone who has ever beaten themselves before the other team got the chance.

Original illustration by Joseph Montano. His signature appears on the back of the shirt.

How we make them

Every shirt is printed to order by our print partner and shipped straight to you. We don’t keep a warehouse of unsold stock, which means your shirt is made for you and takes a few extra days to arrive.