About Us

Chester's Smile is an authentic streetwear brand born in San Diego but with roots in Toronto. Focusing on clothes as the art of storytelling. We emphasize the details from fabric selection to garment construction all the way down to the buttons and stitching. Each item we produce tells a story through its craftsmanship and design.
Dive into the vibrant world of fashion as we blend urban aesthetics with the art of storytelling.

 

Chester's Smile isn't just about clothing: it's about expressing your unique story through what you wear. Join us on this artistic journey where we'll take you behind the scenes of our design process, show you the inspirations behind our collections, and explore how each piece we create tells a tale of its own.

 

We're not just about our brand; we're about building a community of like-minded individuals who appreciate the art of storytelling through apparel. Join us as we feature our supporters, collaborators, and local artists who are leaving their mark on the streetwear scene.