Style school: how to wear this season’s preppy style essentials

Fashion has fallen hard for the preppy look, with blazers, loafers, and rugby shirts just a few of the items resonating with Gen Z this autumn. But you don’t need to have been born after 2002 (or have a starring role in HBO’s Gossip Girl reboot) to experiment with this look. 

The preppy aesthetic, which dates back to 1960s America and its Ivy League college students, has plenty to offer our wardrobes. Not least the fact that it’s loaded with high-functioning staples that appeal to those of us who appreciate clothing that provides both longevity and versatility.

From the checked blazer you’ll return to for seasons to come to the rugby shirt that provides a much-needed refresh for your off-duty look, here’s a guide to the prep stars worth paying attention to this autumn.

For anyone who wants to dip a toe into the preppy pool, the loafer is the perfect place to start. This season’s incarnations are all about simplicity, so seek out soft and supple leathers and neutral shades where you can. A lug-sole loafer is an excellent idea for those who like a bit of an edge to their look. Team with everything from kilts to straight-leg jeans.

The trouser suit has transcended ‘trend’ status to become a wardrobe essential – but there’s still plenty of scope for experimentation, especially if you focus on the jacket. Layered over knitwear or Breton stripes, even the most formal piece of suiting takes on a preppy quality. Checks are an excellent blazer option for anyone keen on embracing the purest incarnation of this trend, but block colours work excellently too.

The rugby shirt has shaken off a stuffy reputation to become a Gen Z essential this winter. The key to joining this stylish scrum is to seek out oversized styles – anything too fitted will look twee. Stripes are far from critical here. A sweater that borrows its silhouette from classic rugby shirt styles is a genius wardrobe addition that will work with everything from denim to your favourite pair of work pants.

The return of the mini skirt is dominating the zeitgeist right now, with high hemlines a way to rekindle our joy in dressing up. But you don’t need a dance floor to enjoy this stylish moment. The mini is everyday attire when worn with thick tights and a sweater. Preppy purists should seek out pleated versions – the kilt is an Ivy League essential – but mini skirts in tactile fabrics are the real secret to success here.

This versatile satchel bag is what you get when you cross classic design with a contemporary spirit. This style is the perfect match for this season’s rebooted preppy aesthetic – it’s also supremely useful. Seek out neutral hues (tan is the prep stars Holy Grail) and don’t be afraid to experiment with textures.