9 Ways To Rethink Preppy — From Shorts Suits To Pencil Skirts

UPDATE: Waterfront happy hours and picnics in the park make us want to channel our inner prepster — but that doesn't mean personal style has to suffer. Here's how to do preppy, your way! This story was originally published on April 1, 2013.
Preppy style is a sartorial hallmark of Washington, where it's no big shock to see Lilly Pulitzer and Lanvin occupying the same sidewalk. And while "preppy" usually denotes a look that's a tad too traditional for some, we've set out to prove that clean and classic doesn't always have to mean bland and boring. Ahead you'll find nine oh-so-easy tricks for revamping old-school staples — from oxford shirts to pleated skirts — and making them feel 100% 2013.
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An anorak snags second place in the race for preppiest topper (right below the classic trench). Still, you can make it feel fresh and fun by mixing bright, sunny shades underneath. Throw in a wedge sneaker for an extra dose of cool.

Photo: Courtesy of Bloomingdale's
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Give that ultra-feminine pleated skirt a bit more edge. Try pairing it with a graphic tee and some tough jewelry to temper all that sophisticated sweetness.

Photo: Courtesy of H&M
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The combo of structure and poppy color make a bright suit jacket a total preppy go-to. Bring yours up to date by opting for a collarless silhouette and adding modern pieces — like a loose tank and cropped denim — in crisp white.

Photo: Courtesy of Zara
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The tomboyish, girl-next-door look is one of our faves, and a classic oxford shirt an essential element for pulling it off. Refresh that old button-down, by layering it under a lightweight neon knit and keeping your hair and makeup natural and effortless.

Photo: Courtesy of J.Crew
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While a sleeveless button-up blouse may have "meh" written all over it on the hanger, all you need to add is a midi skirt in an eye-popping graphic print to shake things up. Even better, this look is fully work-appropriate.

Photo: Courtesy of ASOS
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Think sweatshirts are only for sporting events and nights on the couch? Wrong. Pair the slightly boxy top with a printed mini for the ultimate high-low mix.

Photo: Courtesy of Topshop
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The short suit is gaining momentum as one of spring's biggest trends, but taking it too literally is a one-way ticket to prep-ville. When you experiment with this new take on the classic two-piece, opt for a slim silhouette and a small-scale pattern to keep it modern.

Photo: Courtesy of Nordstrom
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Yes, even a pencil skirt can get a preppy make-under. Pair the structured staple with a soft silk blouse in a saturated hue, and button it all the way to the top for an androgynous flourish.

Photo: Courtesy of Mango
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Like cat-eye liner and ballet flats, the classic white button-up will never go out of style. That doesn't mean, however, that you can't give it your own signature twist. Start by rolling up the sleeves and pairing it with a feminine skirt and booties. Preppy perfection!

Photo: Courtesy of Land's End Canvas