Why preppy style endures
We may have dabbled in all possible trends in fashion through the years and kept many pieces, but when it was time to edit, it was most of the preppy ones that remained. If you look at the fashion houses today and how they have been changing creative directors as quick as fast fashion can knock off their wares, many of them are leaning towards preppy staples: Michael Rider’s silk scarves, popped collars and Keds-style deck shoes at his Celine SS2026 debut and Jonathan Anderson’s pastel trousers and striped ties at Dior SS2026 are following the lead of Miu Miu and The Row who had a headstart in the last seasons. All of them are probably looking at the performance of Ralph Lauren, the king of preppy himself whose full-year sales grew by eight percent in 2025 to $7.1 billion.
Ralph Lauren has always had a following in the Philippines—so popular in the ‘80s that Lizzie Zobel and Mia Borromeo established Regatta which was inspired by all things preppy. Bench had its own take on the style with its sporty, timeless classics.
The look of crisp, white linen shirts—with the gusot mayaman requiring starching and pressing, not to mention frequent washing—is a staple paired with jeans, passed on through generations.
In the late 1890s and early 1900s, the preppy style was a status symbol worn by a subculture of preppies or students who went to college-preparatory and Ivy League schools in the Northeastern United States. These preps were distinguished by a particular subcultural speech, vocabulary, dress, mannerisms and etiquette that reflect an upper class and old money upbringing.
The preps adopted their own kind of uniform—a blend of British tailoring and American sportswear. Polo, sailing, hunting, fencing, crew rowing, lacrosse, golf, tennis and rugby inspired everyday wear and incorporated aspects of traditional British country clothing. Button-downs from Brooks Brothers, which had stores at the likes of Harvard and Princeton, were worn under V-neck knit sweaters together with tweed sports coats, brogues and loafers which were all part of their closet must-haves.
By the 1930s, college women also got into the picture. The release of the first pair of Lady Levi’s in 1934 instantly made jeans a quintessential element of the style. In the 1960s and ‘70s, Perry Ellis and Lilly Pulitzer, influenced by designers like Oleg Cassini, introduced preppy fashion which was popularized by students at sister institutions to the Ivy league: tailored skirt suits, low heels, wrap dresses, shift dresses, and refined jewelry.
However, the look wasn’t limited to American college students. Across the pond, in London, were the Sloane Rangers—a group of West Londoners gravitating around Sloane Square—who were put on the map by Princess Diana back when she was Lady Diana Spencer. They were known for their cardigans and polo shirts. In Paris, they had their own version in the bon chic bon genre (good style, good class) aka b.c.b.g., which Max Azria capitalized on and turned into a label in 1989.
The look was so popular that The Official Preppy Handbook came out in 1980, edited by Lisa Birnbach as a satirical reference guide discussing prepdom with insights on school life at socially acceptable schools, illuminating many aspects of the conservative upper middle class, old money WASP society. It helped democratize preppy fashion by exposing preppy culture to the masses. Economic and cultural shifts actually made universities less exclusive, with preppiness as a subculture following suit.
The Sloane Ranger Handbook followed in 1982 with equal success—a brainchild of Ann Barr and Peter York, features editor and writer, respectively, of Harpers & Queens magazine, who had been documenting the London subculture whose trademark items were Gucci shoes, Hermès scarves, a navy gilet or waistcoat, pearl necklace and pleated skirt. Men wore impeccable suits, corduroy trousers or khakis, a big tweed coat or sheepskin jacket from Burberry or Barbour. Just like the prep one, this handbook was also given to parody although it maintained that while status was something with which you were born, the trappings and wardrobe of a certain kind of elite could be practiced and adopted.
At the same time, mass marketing of brands such as Ralph Lauren and Lacoste moved preppy style into the mainstream which developed a predilection that designers like Marc Jacobs would cater to in the 1990s, putting a twist with lower pant styles, boot cuts, and even having grunge iterations in plaid. Jenna Lyons shook things up at J.Crew in 2008 with shockingly bright colors and sparkle to make it less Nantucket and more fashionista.
Crew has proven preppy’s longevity by reemerging from pandemic bankruptcy in 2020, surviving store closures and the rise of athleisure. The secret is how it can easily adapt to the times. It reflects today’s fashion climate, highlighting the desire to invest in clothes that can be worn repeatedly and styled in a number of ways.
Recent collections channel the style with less of the country club and more of a relaxed vibe, pushing the boundaries of what preppy can be. At Dior, Jonathan Anderson made it modern through styling that appeared undone—ties worn backwards, button-ups uncuffed, collars popped and cable knit sweaters nonchalantly thrown over shoulders. While everything was tailored and crisp, nothing was stuffy since there was an easy, comfortable feeling. At Celine, preppy codes, like button-ups under blazers, were updated with face-swallowing sunglasses, chunky rings on every finger and skinny belts with huge oval buckles. Mithridate layered stripes over contrasting stripes and even threw sequins and fringe to the mix. The key to doing preppy now is to make it unpredictable by doing unusual combinations and contrasts and make it look effortlessly chic.
