The word “preppy” tends to conjure up images of a certain kind of dress, time, and place. If you immediately saw a montage of plaid, stiff school uniforms, organized sports, and New England lighthouses, you’re not alone. But the truth is, it’s 2017, and despite what our sartorially enlightened, edgier adult selves might think, preppy ain’t so bad. In fact, it’s in: One look at this season’s fashion week show goers and it’s clear that blazers — especially the striped and plaid variety — ruled the streets. Only this time, this prep style trademark was worn in ways that made it more inclusive and modern than its strait-laced predecessors.
With the new preppy as our style hero this fall, we explored creative ways to reinvent it in our next installment of #R29StyleStalking with ASOS. Some highlights: tailored silhouettes and trousers mixed with quirky sportswear (read: bell-sleeved, hooded windbreakers) and heavy layering with sweatshirts and hoodies (yep, these aren’t going anywhere fast), all worn by a San Franciscan skateboarding and rollerblading crew for a dose of high-school nostalgia. Check out the video above and the photos below to see how we took these looks for a spin, quite literally.
As if hoodies haven’t already gotten enough play in our wardrobes, they’re back again this season, looking more polished than ever under tailored toppers like this striped blazer. In the same vein, track pants can instantly mellow out a preppy plaid jacket.
Plaid pants can give off some not-so-subtle country-club vibes. But with Converse, sweatshirts, and funky windbreakers — not to mention, skateboards and rollerblades — they look more ’90s grunge than golf.
Or you could go all in with a plaid jumpsuit. Laced grommets and a layered tee give the look a modern, Cher Horowitz 2.0 feel.
Like what you see? How about some more R29 goodness, right here?