About Winston Proper

Winston Proper was born from a cherished father–daughter tradition and a shared love of bold, joyful art. Each year, we return to Santa Barbara’s iconic I Madonnari Street Painting Chalk Festival, where we transform pavement into vibrant, large-scale chalk murals inspired by the subjects closest to our hearts. What began as a personal creative ritual has evolved into an annual artistic journey—one that now lives far beyond the street. In 2023, we debuted a pop-art abstract portrait of Winston, our beloved dog reimagined in vivid color. The piece quickly became one of the festival’s most talked-about works and was later selected as the official 2024 I Madonnari Festival T-shirt design. In 2025, we introduced Poppy the California Bear, an expressive new character who instantly captured hearts and expanded our growing art universe. As festivalgoers asked how they could take these artworks home, Winston Proper naturally evolved into a product line. Today, our designs are available as high-quality limited art pieces, stickers, and canvas tote bags—made to bring color, personality, and story to everyday life. Every year, we introduce a brand-new chalk masterpiece at the festival, and every piece becomes a permanent part of our collection. For retailers, Winston Proper offers distinctive, art-driven products with a built-in story—rooted in tradition, creativity, and joyful self-expression. This is just the beginning.Read their story