My love affair with preppy style began with a sweater—a pistachio green, cable-knit, three-ply cashmere Ralph Lauren crewneck, to be exact. It had exquisite proportions—a skinny, slightly cropped cut, tiny armholes, and narrow sleeves that made your arms look like they went on forever—and the wool was so soft that it felt like a baby’s hair when you touched it (which I did a lot, obviously). In my New York of the late ’90s, it became part of my work uniform: I would wear it to the Vogue office on Madison Avenue with a pair of pale pink silk Dolce & Gabbana flared trousers, my granny’s pearls, and Manolo Blahnik kitten heel sandals in pale suede. On my shoulder: a huge leopard-print Fendi sack that André Leon Talley had given me. (It was quite normal for André to throw a heavenly bag on your desk and say something like, “You need it more than me, darling!” before pirouetting out of sight.)
Soon, I’d added a chocolate brown version of the Ralph sweater to my collection (the “collection” forever remained at a modest two), which I teamed with another pair of Dolce trousers (this time in lime green silk), snake-print shoes, and an L.L.Bean tote monogrammed with my initials in pink letters. Beauty-wise, the Bobbi Brown “no makeup” makeup look reigned (think: an immaculate nude mani-pedi, a subtle stain on the lips, a dash of mascara, and a light tan courtesy of a weekend in the Hamptons).
So began my induction to the world of preppy style—a kind of studiously casual way of dressing that can be traced back to the early-20th-century sports uniforms of East Coast college preparatory schools. While those students rowed and played lacrosse, polo, and tennis, elements of their kit were fast becoming part of an emerging scene that dominated first Upper East Side hangouts like J.G. Melon and then the runways, centering around polo shirts, boat shoes, tweed jackets, and sailing tops that suggested a certain outdoorsy lifestyle. The fact that it began to infiltrate our city wardrobes was largely due to the girls of the moment.
I had arrived in New York in 1997, when the rule of Park Avenue princesses was at its height and their influence within my circle was pervasive: We all wanted to look like Marie-Chantal Miller; her sisters, Alex and Pia; Aerin Lauder; and Tory Burch, who were all in their late 20s and dominated the social and fashion scenes, having evolved a polished, high-maintenance version of Manhattan prep. By day, they dressed in biscuit-colored Marc Jacobs waffle cashmere sweaters, capri pants, and Chanel ballet flats and wore large diamond studs in their ears; by night, for benefits and parties, they were clad in frilled Valentino, Chanel, or Oscar de la Renta cocktail dresses and bedecked in Harry Winston, Verdura, and Van Cleef jewelry; they got married in strapless Vera Wang confections and honeymooned in Maine or at the Mill Reef Club in Antigua. Social gatherings looked like film stills from Whit Stillman’s Metropolitan (1990) and The Last Days of Disco (1998), the latter of which featured Chloë Sevigny in a gorgeous array of preppy party outfits.
My inner prep excelled during summer weekends. From early May to the end of September, I’d disappear to the Hamptons on a Friday afternoon and come back to a sweltering Manhattan as late as possible on a Sunday night. Through an English couple who were friends from my London days, I managed to swing a room in a heavenly clapboard cottage in Amagansett, which I shared with my twin sister, Lucy, who was a fashion editor at a different magazine. (A whole room just for me was too expensive.) The other friends sharing in the rental were Charles Fagan, who was a top executive at Ralph Lauren, and Thom Browne, then a designer at Club Monaco. Paddy Byng, one half of the English couple, also worked for Ralph Lauren.
For a wannabe prepster like me, Paddy, Charles, and Thom were the dream housemates. Charles exclusively dressed in Ralph Lauren and would emerge for breakfast looking like he was ready for sailing in navy cotton trousers with the cuffs rolled up, deck shoes, and a polo shirt with a Fair Isle vest over it. Paddy, ever the upper-class Englishman, dressed with nonchalant elegance in jeans, crisp shirts, and crewneck sweaters. Thom, already evolving his immaculate personal style, looked like he was about to hit Centre Court at Wimbledon and would sip his coffee sporting a neat cardigan, tiny shorts, and white sneakers.
Lucy and I, having visited J.Crew or Club Monaco, where you could pick up the full preppy weekend look for a couple hundred dollars, would join them on the lawn for a lazy breakfast dressed in faded denim miniskirts worn with oversized cotton sweaters in a Pantone of creams; Lilly Pulitzer–inspired shift dresses, which went brilliantly with our Fendi Baguettes; slim-cut jeans and plain white T-shirts from James Perse; all finished with a neat Gucci web belt in the famous green-and-red stripe. We also wore cashmere twin sets in electric yellows, blues, and greens with A-line Prada skirts, a subversive take on what our grannies had worn in the 1950s. The clothes were our passport to daytime activities that included early morning walks on the beach, cycling to the Amagansett farmers market, popping into the Golden Pear for coffee in East Hampton, brunching at the Candy Kitchen in “Bridge” (Bridgehampton), and rifling through the piles of fabulous jeans at the Henry Lehr boutique. Most favorite of all, though, was a shopping moment at J.Crew At-the-Beach, the chic outpost in East Hampton, which sold a range of printed T-shirts (not available in their city stores) that were washed and washed to look as if they’d already been worn for years. In the evenings we’d join friends for clambakes by the ocean or lobster rolls in Montauk and end up back at the house, where we’d chat late into the night.
Perhaps, then, as we collectively pine for a blissful offline summer break, it isn’t so surprising that this fresh-air wardrobe of seasonal hijinks is back for 2024. It was exquisitely executed on the Miu Miu runway, where navy polo shirts, worn over mannish cotton shirts, look brand-new again; tiny shorts with drawstring waists evoke Nantucket or Cornwall summers; and huge, squishy bags bulging with rope sandals and distressed white deck shoes are the kind of must-haves that have fashion TikTok ticking madly. (Even the word itself is back—sort of: For the middle school crowd of the moment, “preppy” means less subdued sporty chic, more Regina George in Mean Girls.) It’s a refreshing antidote—undone, messy, and cool in an utterly unlikely way—to the trends that now seem tired: overly studied “quiet luxury” (snooze) and the glitzier trappings of Y2K fashion. Consider it an opportunity to get creative within the bounds of your budget, just like we did when packing for those long Hamptons weekends. Slide on a pair of vintage Tory Burch flats, knot a Ralph Lauren cable-knit cashmere sweater about your neck, have a tailor retool last year’s jeans into a no-nonsense slim leg, and slide a copy of The Official Preppy Handbook (published in 1980) into your weekender. My advice, from one wannabe prepster to another: Always bear in mind that rules are there to be broken.
Wives Like Us by Plum Sykes (HarperCollins) is published on May 14.