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If I were to describe my high school aesthetic in a nutshell, certain pieces of clothing come to mind: popped candy-color Ralph Lauren polos, little plaid skirts, Tommy Hilfiger–branded tennis dresses, rugby stripes, checked Bermuda shorts—you get the picture: I was one helluva preppy kid. But after I graduated from high school, so, too, did my personal style. I eased away slowly from it at first. (Because, guess what? It's rather easy to nail collegiate prep as a prep in college.) But when you commit to one aesthetic for too long, it will inevitably flip—so I went through a phase of bandage dresses, going-out tops, and micro-short skirts before deciding that a Serious Adult wardrobe meant stark minimalism and mostly black clothing. Now my style is something that can be best described as a blend of low-key peacock-ing, easy comfort (mostly out of convenience and laziness), and what I hope comes off as elevated effortlessness—basically, I haven’t touched a polo shirt since I had to sit through an AP class. So when designers all over the industry, from Italian labels like Max Mara and Fendi to Rihanna, for her Fenty x Puma label, collectively decided that prep was in for fall ’17, nostalgia hit me in a major way.
I expected this from the J.Crews of the world. (And, sure enough, the retailer's fall ’17 collection delivered with rugby stripes styled with dramatic tulle-lined skirts, khakis paired with off-the-shoulder tops, nautical peacoats shrugged over Fair Isle knits, and so on.) But the undercurrents of prep extended far beyond the mall stalwart: There were reimagined khaki silhouettes at Creatures of Comfort, sharp, plaid suiting at Rosie Assoulin, cool argyles at Marc Jacobs. Rihanna staged her Paris Fashion Week presentation at the National Library of France, an apropos backdrop for the schoolgirl skirts, teeny knit polos, and varsity stripes that would parade down the wooden tables during the show.
Much like how every runway-to-real-life scenario begins, I started dreaming up ways to (re)integrate preppy elements into my wardrobe without it feeling completely unnatural. I was hesitant, of course: Ask anyone to reminisce about any of their throwback looks, and their first instinct is to inwardly cringe. But I charged ahead, confident that I could pull these sartorial relics of high school and have them telegraph "I'm a put-together adult who has her life figured out" and not "awkward teen trying not to be awkward." Thus, this story was born.
Ahead, I pull the five preppiest garments I could think of: a polo (in Nantucket red, of course), a fitted blazer (in a nautical color scheme), Bermuda shorts (in the brightest turquoise available on the market), a neon shift (printed with seashells, obviously), and boyfriend-style khakis (has the nostalgia hit you yet?). Then I incorporated them into outfits that not only showcase each garment but prove that it’s possible to embrace the preppy trend, even when it’s really no longer your style.
THE POLO
The only way for minimalists to even consider color? When monochromatism is at play.
My instinct toward color-coordination kicked in when faced with a Nantucket-red polo: I pitted it against a striking scarlet, pleated skirt, then added interest with stacked, lace-up sandals sandals, and a structured cross-body bag.
The author is wearing a Nantucket Reds polo styled with a Victoria, Victoria Beckham skirt, Ray-Ban aviator sunglasses, a Loewe bag, and Miu Miu sandals.
THE BERMUDA SHORTS
As someone whose collection of shorts is exclusively made up of denim cutoffs, I must confess that this challenge had me stumped. Bermudas get a bad rap for looking dated, so I countered it with a statement shirt by Caroline Constas (a.k.a. the Queen of Statement Shirts) and trendy accessories like a woven-straw purse (I picked this one up in Hong Kong) and tassel sandals (which I bought in Paris).
The author is wearing Vineyard Vines shorts styled with a Caroline Constas top, Gucci sunglasses, Ray Beams bag, and Antik Batik sandals.
THE NAUTICAL BLAZER
This might be the preppiest out of the bunch, but I’m not mad about it—actually, it's my favorite. For this look I played with proportions, anchoring a long shirtdress and high-waisted Levi's with a tailored blazer.
The author is wearing a Blaque Label blazer styled with an Everlane shirt dress, vintage Levi’s jeans, Quay sunglasses, and Sarah Flint pumps.
THE PRINTED SHIFT DRESS
I tend to shy away from prints in my everyday wear. But when faced with something as loud as a neon seashell-patterned dress, is there any approach other than to wholeheartedly embrace it? So I leaned in, piling it on with a pair of patterned flares, a leopard clutch, and pastel sunglasses.
The author is wearing a Sailor Sailor dress styled with Comme des Garçons pants, an Aerin clutch, Rowley Eyewear sunglasses, and Steve Madden sandals.
THE KHAKIS
A look made famous by nineties Gap ads, the white button-down and khaki combo is perhaps the ultimate preppy (slash business-casual) outfit. For a current, street-style-y take, I added one more layer: a little floral cami I picked up at Zara several seasons ago. I polished it off with mirrored cat eyes and stiletto pumps.
The author is wearing J. Crew pants styled with a Banana Republic shirt, a Zara crop top, Marc by Marc Jacobs sunglasses, and Manolo Blahnik pumps.
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