Seasonal Checklist: Your Guide to Preppy Style

Welcome to the Prep-A-Torial... your official guide to preppy style by personality.

April 19, 2018
in Style

Go ahead, pop that collar. At its core, prep style has always been about breaking the rules. As part of the original prep iconography back in 1935, who better than us to make sure that humor, courage and a little rebel twist finds its way into modern prep?

So we’re here with a guide. And we’re breaking it down by personality. Because you know there’s one in every country club… or city pub.

Meet the Summersault

Her motto? It’s always summer somewhere. Which means there’s a boat. And a gin + tonic. And stripes. And navy.

Outfit #1: Refuses to be seen without the neck scarf. It’s the breakout accessory of the summer–and doubles as a headband in a pinch.

Outfit #2: The striped blazer is for show. It says: If this job doesn’t have summer Fridays, she doesn’t have this job. Plus boat shoes, because, impromptu yacht parties.

Meet the Continental

He’s just returned from a trip abroad and is still carrying a torch for a European nod or two.

Outfit #2: Cropped khakis because… all the better to show of the boat shoe game. It’s the one look all continents can agree on. Is this the start of world peace?

Outfit #1: Woke up early to perfect the brush forward (hellooo, cowlick control). Would never chance ruining the do by actually wearing those leather headphones.

Meet Sir Croquet

He can’t get enough of the Royal Tenenbaums, tennis shoes, and anything fresh and white.

Outfit #1: Never met a layer he didn’t like. Add the Sperry CVO. The original tennis sneaker, born in 1935. Pro tip: Carry a Tide stick.

Outfit #2: Sweater again. This time, graphic. A crisp conversation starter, which is always crucial at cocktail parties. Must add: the Button Down. A.K.A. the sweater’s BFF.

Meet the Coxswain

She loves everything boxy, rows in her own direction, and has a style that’s 100% androgynous.

Outfit #1: The tied sweater adds more stripes, and those jean shorts are *perfectly* worn in. Achieved by never taking them off.

Outfit #2: High socks are a three-fer. They tackle high-powered AC, sweaty sneaker feet, and the innate need for even more stripes. Finish with the nautical sneaker. Boat ready and fuss-free.

Meet the Academic

He’s all about loafers – always. Plus khakis, button-ups, faded polos. All of it forever (perfectly) rumpled.

Outfit #1: The rumpled blazer. Of course rumpled. Everywhere. Over everything. Shower steam as desired.

Outfit #2: Skinny chinos flaunt calf and thigh work. Oh, and laidback loafers. Contrast stitching and burnished leather show the quality is serious – even when it looks effortless.

Meet the PBI

She heads straight from the airport to Worth Avenue. She has a love for neon, print and cardis. Preferably together.

Outfit #1: The draped jacket. Must be willing to sacrifice the ability to dance, raise a glass, and well, move. It’s all for the #OOTD.

Outfit #2: The Seaport loafer. If she could wear them every day, she would. But not a big fan of outfit repeating.

Shop our official Prep-A-Torial here, and tag your photos on Instagram with #SperryMyWay to show us your preppy style.

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