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 and the wool was so soft that it felt like a baby’s hair when you touched it – which I did a lot, obvs. I was living in New York around the time I acquired this sweater, in the late ’90s, and it became part of my work uniform: I would wear it to the American 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 the late, legendary writer and stylist André Leon Talley gave me. It was quite normal for André to appear at 10 in the morning, throw a heavenly bag on your desk and say something like, “You need it more than me, darling!” before pirouetting out of sight.
Before long, I’d added a chocolate brown version of the Ralph sweater to my collection of one (the “collection” forever remained at a modest two), which I teamed with another pair of Dolce trousers, snake-print shoes and an LL Bean tote with my initials monogrammed on it in pale pink letters. My bag never concealed a particularly large make-up bag as, beauty-wise, the Bobbi Brown “no make-up” make-up 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).
And so began my induction to the world of “prep” – an American term that derives from the East Coast private college-preparatory schools attended by teenagers before they moved on to Ivy League universities. While students spent their recreation time rowing, playing lacrosse, polo and tennis, elements of that classic sports kit were fast becoming part of an emerging style scene that dominated Upper East Side hangouts. The preppy look centred around items such as polo shirts, boat shoes, tweed jackets and sailing tops that pertained to a certain outdoorsy lifestyle. The fact that it began to infiltrate our city wardrobes (London had the Sloane Ranger) 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, socially and aesthetically, was all-pervasive.
My inner prep excelled during summer weekends. From early May to the end of September, I’d disappear off 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 for the summers and my twin sister, Lucy, who was a fashion editor at a different magazine, shared it. The other friends sharing in the rental were Charles Fagan, who was a top executive at Ralph Lauren, and Thom Browne, who was 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. Lucy and I, having visited J Crew or Club Monaco in the week, where you could pick up the full preppie weekend look for a couple of hundred dollars, would join them on the lawn for a lazy breakfast dressed in a variety of outfits that we thought set the tone for the relaxed, outdoorsy weekend ahead: 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, finished with a neat webbing belt by Gucci. The clothes were our passport to extensive daytime activities, which included early morning walks on the beach, cycling to the Amagansett farmers market on the bikes we rented for the summer and rifling through the piles of fabulous jeans at the Henry Lehr boutique. 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 surprising the fresh-air wardrobe of high-jinx pursuits is back for 2024 (though the inhabitants of New York’s Upper East Side would argue it never went away). 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 are must-haves that have already got TikTok ticking madly. It’s a refreshing, sporty antidote to the trends that now seem tired: overly studied “quiet luxury” (snooze) and the glitzier trappings of Y2K fashion.
This new, revised take on the look of a certain strata of the American upper class is undone, messy and cool in an utterly unlikely way. 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 and slide a copy of The Official Preppy Handbook (published in 1980) into your weekender. My advice, from one wannabe prepster to another: bear in mind that rules are there to be broken.
Wives Like Us by Plum Sykes (Bloomsbury, £19) is published on 14 May
