On an island that can take casual to a whole new level, it’s refreshing to cross paths with our own Lady Katherine Iverson and her well-heeled companion and medic alert dog, Desi. Although Iverson is always dressed to the nines and more often than not adorned with pearls, it’s the mop-like pooch—a sweet-tempered Havanese whose parents were show dogs—who gets all the attention. The photo-worthy duo is oft spotted earning fans at B.I. Barkery, Eagle Harbor Books, or Bainbridge Arts & Crafts. This shot was taken on Madrona Lane by a group of young Japanese tourists who went crazy for Desi, taking their own pictures of the pair to send home to friends.