Preppy style essentials: class of 2025

Some things never go out of style and the preppy look – with its high-performing wardrobe staples, such as blazers, button-down shirts, knitted sweaters and loafers – is one of them. These key pieces combine to form a fashion-girl-approved finish that looks chic but also – whisper it – expensive. Here’s our definitive guide to the current crop of preppy stars, which we guarantee you’ll return to season after season.

The preppy aesthetic dates back to 1950s America; inspired by the wardrobes of the wealthy, chino-clad college students who attended Ivy League preparatory schools – hence the name – it’s been a catwalk and celebrity styling mainstay ever since. And not just in Gossip Girl (the Noughties show that notably took the look and ran with it, xoxo). 

The real reason this style still shines bright? It’s made up of versatile basics, worn with a twist. Think: a rugby shirt over a miniskirt, or barrel trousers teamed with loafers. Extra style points for donning the associated iconic prints – that’s argyle, stripes or gingham – and for knotting your sweater around your shoulders…

Hot off the catwalks, the rugby shirt has become the ultimate wardrobe staple for your off-duty look. The key to joining this stylish scrum is seeking out oversized styles – anything too fitted will look twee.

Worn over a shirt for the ultimate preppy look, you can reboot this classic style by playing with volume and pairing an oversized sweater vest with wide- or barrel-leg trousers.

To dip a toe into the preppy pool, the loafer is the perfect place to start. Comfy yet chic, this shoe’s shape is all about simplicity: soft, supple leathers in neutral shades. Go sock-free and team with straight or barrel-leg jeans.

If you thought this headgear was only for celebs-in-hiding or soccer moms, it’s time to have a rethink. A baseball cap in a neutral colour is the perfect nod to 2025’s preppy reboot.

A quintessentially preppy piece, the blazer works hard whether layered over structured knitwear or casual Breton stripes. Check finishes are an excellent option for anyone keen on embracing the purest incarnation of the look, while classic block colours go with everything.

The perfect foundation for a preppy outfit, a miniskirt looks great when teamed with a chunky sweater and blazer. Purists should seek out pleated versions – the kilt is an Ivy League essential – or any high hemline in a tactile fabric.

Versatile and super useful, the crossbody satchel is the result of blending a classic design with a contemporary spirit. Seek out versions in neutral hues (preppy fans love tan – it’s their Holy Grail) and don’t be afraid to experiment with textures.