Celebrate the spirit of the island with the Anguilla Icons T-Shirt Collection by Totally Anguilla, a unique series of illustrated shirts that pay tribute to the people behind the island’s most famous spots. From the owners of beloved beach bars to the faces of Anguilla’s legendary restaurants and seaside hangouts, each shirt captures the essence of what makes this Caribbean destination unforgettable — its warm, welcoming personalities.
Every design in this series features a custom cartoon portrait of a real Anguillian icon, reimagined in a colorful, vintage-inspired style. Whether it’s a smiling chef known for sunset dinners by the sea, a friendly bartender who makes the island’s best rum punch, or the couple who turned a hidden cove into one of Anguilla’s most cherished beach clubs — these shirts bring their stories to life in fun, wearable art.
Made from high-quality, soft cotton and printed in vibrant, lasting colors, each t-shirt is designed for both comfort and island flair. The illustrations highlight the relaxed charm of Anguilla, featuring palm trees, turquoise waters, and cheerful details that reflect the tropical setting of each featured location.
The Anguilla Icons Collection is more than a souvenir — it’s a celebration of community, creativity, and the people who make Anguilla special. Locals and travelers alike will recognize familiar faces from Sandy Ground, Shoal Bay East, Meads Bay, and beyond. Each shirt tells a story of passion, hospitality, and island pride, making it the perfect keepsake for anyone who loves Anguilla’s vibrant culture.
Whether you’re collecting them as mementos of your favorite places or gifting them to fellow Anguilla fans, these shirts are designed to spread smiles and memories. They’re wearable tributes to the island’s character — a fun, artistic way to show your love for Anguilla’s people and places.
Explore the full lineup and find your favorite island personality in the Totally Anguilla Icons T-Shirt Collection, where every design captures the heart and humor of the Caribbean’s friendliest island.