Sperry Boat Shoes Lead the Modern Preppy Revival Among New Generations

Sperry's classic boat shoes, long associated with preppy American style since their prominent feature on the cover of "The Official Preppy Handbook" in 1980, are experiencing a notable resurgence. Historically favored by icons like John F. Kennedy, these footwear pieces symbolize a blend of casual elegance and coastal sophistication. Recently, they have gained popularity among a new generation of fashion enthusiasts, driven by runway appearances, streetwear influences, and the sport of sailing. Celebrity endorsements from Jennifer Garner, Jennifer Lawrence, and Emma Corrin have further elevated their status in 2025. This renewed interest has translated into a 28% increase in boat shoe sales in the first half of the year, according to Circana research. Fashion experts note that contemporary styling combines vintage elements with modern trends, moving beyond traditional preppy looks. The trend's revival is also rooted in nostalgia, reflecting a broader fashion obsession with mid-century collegiate aesthetics and heritage-inspired designs. Major designers like Miu Miu, JW Anderson, Jacquemus, The Row, Burberry, and Prada have showcased boat shoes on their runways, fueling consumer e...