The ‘old money’ look that’s back in fashion

You can forget about the idea of being too cool for school – fashion wise, at least. “School”, in the American Ivy League university sense of the word, is enjoying a renaissance that looks set to run and run.

The preppy look has been going in and out of style for more than a century, but it originated in the US, at the elite colleges on the East Coast. Brooks Brothers and J Press opened stores on campus, targeting monied students with smart-casual clothing for academic life and popular pastimes such as rowing, polo and golf, and lo, the “prep” aesthetic was born.

It’s been ridiculed over the years – the first book dedicated to preppy fashion was a parody, and who could forget Carlton in 1990s sitcom The Fresh Prince of Bel-Air – but equally it’s been championed by some seriously stylish figures too; Dustin Hoffman in The Graduate, Princess Diana, all of the Kennedys. Ralph Lauren built a $7 billion brand on it.

Jack Carlson, founder and creative director of Rowing Blazers, has built a brand on the preppy look too. “The essential building blocks for preppy style are plenty of colour, the rugby shirt, smart pants and an interesting cap that you probably picked up on your travels,” he says. “And of course, the finishing touch to the look is always a great blazer – of course I would say that; I created the Rowing Blazers brand having delved into the history and culture of the club blazers and their significance within collegiate style.”

The British equivalent is best described as a Jilly Cooper Rupert Campbell-Black kind of aesthetic. You might call it Sloaney; it’s been dubbed “old money” on TikTok. Perhaps we’ll be adding football jerseys to our preppy arsenal, after we’ve all devoured Cooper’s latest book, Tackle!, out now. Add that to your reading list along with Donna Tartt’s The Secret History.

Chestnut blazer, £199, and Dyce knitted rugby top, £120, both Beaufort & Blake

There’s no shortage of real-life muses: Taylor Swift, Pharrell Williams, Jenna Ortega in Netflix’s Addams Family reboot Wednesday, model Hailey Bieber. It’s on the catwalk at Miu Miu and Thom Browne, while JW Anderson is bringing his take on the look available to the masses via his collection for Uniqlo – the autumn/winter drop has just landed in stores and is selling out rapidly. There is truly a take on preppy for everyone; minimalist, maximalist, nostalgic, goth, you name it.

There are several very good reasons why the preppy look is enjoying a particular resurgence right now: it’s associated with wealth, which, in a cost of living crisis, holds a lot of appeal. Class, too – it reflects “old money” rather than the logomania of “new money”. Its origins as a uniform, of sorts, for students at Ivy League universities means that it also carries an association with an intellectual mindset – not to mention youth.

There’s an order and polish to it – in an unstable world, even the most trivial sense of control can feel reassuring – and there’s no barrier to entry either: this is a look that can genuinely be embraced by anyone, not least because the elements required are probably in your wardrobe already – yes, you’re on trend without even realising.

“There is a certain section of ‘Ivy’ that is just clothes,” says Derek Guy, an authority on menswear whose knowledge of the topic has earned him half a million followers on X (formerly Twitter). He speaks on Avery Trufelman’s excellent deep dive into the origins of preppy style on her podcast Articles of Interest: “Flat front chinos [are] just clothes. An Oxford button-down is just a dress shirt. It’s just what people wear. These things have become so popular, so consumed by everybody, that they are no longer an aesthetic, they’re just clothing.”

Nailing the preppy look is all about the styling: socks with loafers; a jumper draped over the shoulders; a baseball cap with a blazer. It’s good quality classic clothes treated casually, because, the look implies, you don’t need to save them for best because all you wear is best.

“The perfect outfit formula here is to layer, layer, layer,” says Libby Page, market director at Net-a-Porter. “The Gucci striped cotton poplin shirt is the dream base, with a Lisa Yang Miko cashmere vest and paired with a loafer; I always look to The Row leather loafers to work with just about everything from any wardrobe.”

College sweatshirts, £34.90, JW Anderson for Uniqlo

Just be careful not to take it all too seriously. “An irreverent spin is the key to carrying off preppy style so it doesn’t feel Sloaney or stuffy,” says Carlson. “It needs to be approached with a sense of humour – it should make people smile.”

Ready to get stuck in? Read on for your preppy style toolkit…

The rugby shirt

Nobody expects you to play any actual rugby, this garment is purely for looking like you have a vague idea of what’s going on in the Rugby World Cup. It’s also a shortcut to low-key polish thanks to that face-framing collar. Team with jeans or chinos, wear to the pub, and do your best impression of a wayward Ivy League student skipping lectures.

Unisex Jagger stripe rugby shirt, £215, Rowing Blazers; Men’s colourblock cotton rugby shirt, £195, Drake’s; Women’s cotton striped rugby-style top, £45, Cos

The pleated skirt

It doesn’t matter if your skirt is mini, midi, or knee-length, as long as it has pleats – a kilt-style design is also high on prep factor. One member of the Telegraph fashion desk has been wearing her old tartan school skirt, which wouldn’t look out of place on a Vivienne Westwood catwalk. Gents, if you fancy partaking in this element of the preppy uniform, I suggest taking a look at the offering of New York-based menswear designer Thom Browne, who makes a very strong case for the men’s skirt suit.

Pleat and button midi skirt, £149, Plumo; Brora Scottish mohair-wool blend mini kilt, £289, John Lewis; Neah pleated midi skirt, £79, Hush

The blazer

You don’t need to be a member of a traditional club, such as White’s or Mark’s Club, you just need the right kind of blazer to look like you are. Go for navy double-breasted with gold-tone buttons, a contrast trim (as seen at Gucci), or something tartan (à la Saint Laurent) to really fit in. Avoid patches or insignia though, which strays a little into fancy dress territory.

Men’s pure wool checked blazer, £160, Marks & Spencer; Miller striped piping Dickey jacket, £‌698, Veronica Beard; Men’s flannel Club blazer, £350, Gant

The baseball cap

The A-list’s favourite “incognito” accessory is also a preppy essential, as it has the capacity to imbue a classic shirt and blazer with casual nonchalance. The muse here is Princess Diana leaving the Chelsea Harbour Club, or JFK Jr sailing on Cape Cod. If it bears the logo of a polo, rowing or tennis club, all the better.

Cashmere baseball cap, £195, Luca Faloni; Sporty & Rich unisex cotton baseball cap, £55, Selfridges; Polyester and wool-blend baseball cap, £20, John Lewis

The knit

Wear it if you must, but this is a garment best draped over the shoulders, with the arms knotted at the chest. It can be a classic crewneck, a cable knit, or for extra preppy points, a V-neck cricket jumper. Nostalgic, novelty motifs work well too, like the Ralph Lauren teddy bear. It should be relatively heavyweight in order to withstand those East Coast winters.

Cable knit Merino wool jumper, £285, Sunspel; Glen plaid wool cricket jumper, £399, Polo Ralph Lauren; Babar sports car golf sweater, £220, Rowing Blazers

The socks

Step away from the trainer socks, the preppy look welcomes visible hosiery, whether it’s a traditional Argyle, collegiate stripes or an athletic style. Best teamed with retro trainers or loafers (see below).

Women’s athletic socks, £9, Arket; Unisex Heattech anti-odour socks, £7.90, JW Anderson for Uniqlo; Unisex cotton argyle socks, £22, Genevieve Sweeney

The loafers

Smart, comfortable, and most of all, classic, the loafer is by far and away the preppy dresser’s most loved shoe. Chunky styles feel a little more contemporary, ditto an oversized snaffle, like the Boden ones here. Tassels will appeal more to traditionalists. Have them monogrammed for a real preppy power move.

Women’s Iris snaffle loafers, £110, Boden; Women’s Cherry loafers, £260, Duke & Dexter; Men’s Weejuns Larson penny loafers, £200, GH Bass

The silk scarf

This should look like you’ve borrowed it from Granny, whose estate you will one day inherit, preferably adorned with chain or equestrian motifs. If it’s not Hermès, choose something that looks like it is.

Victoria silk scarf, £149, Holland Cooper; Bloomfield blue silk square scarf, £39.95, Joules; Brides de Gala tartan scarf 45, £190, Hermès