How to Wear the Preppy Trend in 2025

Words by Tony Wilkes

“Basic style for the man never changes because the man never changes,” wrote Lisa Birnbach in her satirical The Official Preppy Handbook (1980). “There is never, ever, a new look for the man.” Satire it may be, but Birnbach does speak some truth. The preppy uniform – crisp Oxford shirts, tweed blazers, chunky knits, polos, loafers and corduroy trousers – is a case in point. These collegiate wardrobe classics have never gone away, nor has preppy as an aesthetic. But that’s only part of the story. Though the look is regularly revived, it never returns quite the same. Each decade has its own unique take on men’s preppy style.

So, what does ‘preppy’ look like now? A men’s trend to know for Spring/Summer 2025, Ivy League prep has appeared in the collections of Rhude, Fendi, Wales Bonner and Drôle de Monsieur – the two latter being new arrivals at Harrods this season. Preppy staples have been donned by A-listers including Josh O’Connor, A$AP Rocky and Tyler, The Creator. On TikTok, the mood arrives through the lens of #oldmoney – a hashtag with more than one million posts to date. Need further proof of the preppy trend’s staying power? From 2019, eBay sales of Birnbach’s out-of-print handbook doubled to 600 copies a year, reaching prices over £1,700.

“There is something sort of escapist and an element of idealism to it,” professor and founding member of the Preppy Handbook Fan Club Matthew Longcore told The Wall Street Journal. Before it was a trend, preppy was as much a lifestyle as a look. Born at American prep schools in the 1950s, the uniform symbolised education and privilege. Then, in the 1980s, prep went mainstream – famously harnessed by Polo Ralph Lauren with a look so appealing the brand now stands as a global empire.

In 2025, ‘preppy’ combines history and the classics with a subversive twist. This in itself is a nod to the genre’s origins – conceived by Ivy League students who ditched their suits for something more relaxed and comfortable. On their trajectory to mainstream popularity, preppy staples have also long been championed by pioneering Black creatives, such as Miles Davis and James Baldwin. This often-overlooked heritage has fed into the collections of the late, great Virgil Abloh, Grace Wales Bonner and Pharrell Williams for Louis Vuitton.

This creative energy fuels the preppy resurgence of 2025. Proportion is key. Look to oversized knitwear – a Fendi sweater vest with bold stripes and statement placket – or Prada’s shrunken V-necks and cardigans under which spill crinkled shirt hems and cuffs. Elsewhere, see wide pleated trousers (backed by Harry Styles, S.S.Daley makes some of our favourites this season) worn with a top in a regular fit, as well as suits cut loose that are smart, comfortable and transition easily from work to play.

Nailing the preppy trend in 2025, though, is most often a question of styling – specifically mixing high and low, formal and casual. The best examples can be seen on the runways. For Spring/Summer 2025, Rhude paired a traditional shirt and tie with a leather varsity jacket, while Wales Bonner teamed classic striped knitwear with a utility jacket and shorts. A sharp suit worn with sportswear items will also nail the balance. Tyler, The Creator juxtaposed a traditional preppy outfit with a puffer jacket and deerstalker cap – surely the winner, if we had to name one, of today’s neo-prep mood.