Tipsy Skipper, a promising new upstart, is run by Kearsley Lloyd, who oozes Prep pedigree (degree from RISD, nefarious pirate relatives, internships at Vineyard Vines and Lilly Pulitzer - oh, and her name is Kearsley). Tipsy Skipper’s Ballet Flats ($120) come in playful prints trimmed with grosgrain ribbon, and are a must have for your summer wardrobe.