My love affair with preppy style began with a sweater—a pistachio green, cable-knit, three-ply cashmere Ralph Lauren crewneck. It had exquisite proportions and soft wool that felt like a baby’s hair. This sweater became part of my work uniform in New York, paired with pale pink silk trousers, pearls, and Manolo Blahnik heels. I eventually added a chocolate brown version to my collection. Preppy style traces back to early-20th-century sports uniforms of East Coast college preparatory schools and was popularized by socialites like Marie-Chantal Miller and Tory Burch.
In the late ‘90s, Park Avenue princesses influenced the fashion scene with a polished, high-maintenance Manhattan prep look. By day, they wore cashmere sweaters and capri pants, while evenings were filled with frilled cocktail dresses and designer jewelry. Social gatherings emulated film stills from movies like Metropolitan and The Last Days of Disco, with Chloë Sevigny showcasing preppy party outfits. Summer weekends were the highlight for my inner prepster, spent in the Hamptons with friends and dressing in J.Crew or Club Monaco preppy looks.
Weekends in the Hamptons were filled with activities like beach walks, farmers markets, and brunching, all while sporting a variety of preppy outfits. From denim skirts and oversized sweaters to Lilly Pulitzer–inspired dresses and vintage T-shirts, our wardrobes were the key to our daytime adventures. Evenings were reserved for clambakes by the ocean and late-night chats with friends. Preppy style made a comeback in 2024, with designers like Miu Miu showcasing navy polo shirts, drawstring shorts, and oversized bags reminiscent of summer vacations in Nantucket or Cornwall.
Returning to the carefree, outdoor wardrobe of preppy style offers a refreshing break from current trends. It provides an opportunity to get creative within budget constraints, much like packing for long weekends in the Hamptons. Embracing preppy style today means mixing vintage pieces with modern essentials and breaking traditional style rules. Plum Sykes’ novel, “Wives Like Us,” delves into the world of preppy fashion and the influence of socialites and fashion icons on the style scene. As someone who appreciates preppy style, I believe that this timeless aesthetic will continue to inspire and influence fashion for years to come.
