Preppy might be having a resurgence, but please don’t make it perfect
I didn’t expect to see pleated skirts, headbands and polo shirts dominate my feed this year, at least not outside of a what-they-wore-at-Wimbledon post. But here we are, in 2025, watching the return of preppy fashion unfold before our eyes. It’s subtle in places (a rugby stripe here, a loafer there) and full-throttle in others (a rugby polo worn with a pleated skirt and a silk scarf and a loafer) – especially on TikTok.
https://www.tiktok.com/@alexballardd/video/7474305140921617694
There’s something fascinating about the way preppy style keeps cycling back. Just when we think we’re all about ‘quiet luxury’ or chaotic layering or normcore minimalism, along comes a pleated skort and a ribboned ponytail to remind us of the enduring power of prep. But one could argue that there’s an element of this aesthetic (ie. a perfectly pressed button up shirt) that never really gets shoved to the back of the wardrobe anyway, right?
According to Instagram account Data But Make It Fashion, online fashion coverage and Google searches for preppy fashion were up 66% YOY in June. Today’s take on preppy style isn’t as stiff and elitist as past iterations of the trend though, it’s cheekier, looser, and actually way cooler because it’s got some personality about it. A little rumpled, a little rebellious. It’s Ralph Lauren after one too many martinis or Blair Waldorf if she’d ended up at art school.
The current wave feels less about fitting into a country club and more about playing with archetypes. Oversized blazers with short shorts when the weather warms up a bit, and tennis whites with beaten-up sneakers. Crisp collared shirts might be buttoned all the way to the top, but wear them with a worn leather jacket and layered with beaded necklaces and you’ve got some polish without being too precious or perfect.
If you’re looking for some inspo, there are plenty of fashion content creators working the trend into their daily wardrobes and giving it their own spin, such as Kiwi Lauren Brodie @elbeefrivilousfashion who loves a statement collar and rugby polo. Across the ditch, I’m also consistently inspired by Naima Fatema @lil_bangla, the head of social for Shameless Media, who styles a pleated tartan skirt to perfection.
Fashion’s love affair with nostalgia is naturally fuelling the flame. There’s a generation of people now dressing like the characters they obsessed over in the 2000s or perhaps discovering them for the first time. Blair, Serena van der Woodsen, Cher Horowitz, even Rory Gilmore. It’s not about copying those looks exactly, it’s about remixing them to give them edge and inject some mischief into all that structure.
The thing is, preppy clothes have always had a kind of quiet confidence built in. A boxy knit vest or a crisp shirt are items that work for myriad occasions and when paired together, make you look instantly put together. There’s a comfort in those clean lines and a familiarity to the styling that can bring a sense of ease in a world where microtrends reign supreme.
There’s a reassuring sustainability element to it too, with many of the core elements of preppy style likely hanging right there in your wardrobe as we speak. And if not, you can bet your bottom dollar your local op shop has a button-up shirt or silk scarf just waiting to be reworn in a new way.
So, is preppy back? Yes, but not as we once knew it because it’s not about perfection, it’s about the mix. It’s about rolling up your sleeves (literally) and reminding yourself that sometimes, getting dressed with a few juxtaposing elements is the key to a good outfit, whether you’re leaning hard into an Upper East Side aesthetic or just giving it a little nod.
Either way, I think Blair would approve.
