Your Cheat Sheet to Preppy Style

Let two of the most preptastic bloggers we know lead the way to yacht-club fabulousness.

By: Sarah Zlotnick

All photographs by Katie Warren.

When it comes to fashion, Washington has a serious case of split personality disorder. From the flannel-wearing hipsters in Columbia Heights to the slick suits on K Street, each neighborhood has its own look. And where would we be if we didn’t mention the pastel-wearing prepsters of Georgetown? With this style, there’s a fine line between fabulous and costumey—and no one walks it as impeccably as law students/platonic lifemates Lauren Wynns and Van Bloys, the duo behind the fashion and lifestyle blog Necessary & Proper. Read on for their ace tips for mastering the aesthetic without looking like a popped-collar tool.

Top five wardrobe essentials:

For women: colored pants (denim or tailored silk), trench coat, a silk blouse (bonus points for one with an unusual neckline or pattern), an equestrian-inspired blazer, and a colorful shift dress.

For men: A navy blazer, Cordovan lace-ups, gray flannel trousers, an oxford shirt, and a cashmere V-neck sweater.

Accessories no prepster should be without:

Women: large sunglasses, a piece of family jewelry, and a dog (any kind of retriever or hunting dog will do).

Men: A sterling silver monogrammed belt buckle, a good pair of polarized sunglasses, and a fabulous watch.

Three pairs of shoes every prepster should own:

Men: Tod’s driving moccasins, L.L. Bean Bean boots, and Cordovan tassel loafers.

Women: A nude pump or wedge, smoking slippers, and riding boots.

Style rules you should never break:

No socks with loafers.

Wear color. Everyone looks better with at least a little splash.

Style rules you should definitely break:

Minimalism. Have some fun—layer shirts, sweaters, jackets, and jewelry. You can keep a classic vibe going without going totally bare bones.

Nobody needs to look like they’re living in a J.Crew catalog all the time. Shake it up! Dress down!

Outfits that will never go out of style:

For women: A shift dress, pumps, and a cardigan; a bikini, an oxford, a straw hat, and thong flip-flops; and white jeans and vibrant tunics.

For men: Oxford shirts and cashmere cable knits; navy suits and repp ties; and Vilebrequin swim trunks and colorful Lacoste polos.

How to translate preppy style to the workplace:

The key is to not go overboard. Don’t wear a patterned sock with tassel loafers, suspenders, a bow tie, horn-rimmed glasses, and a pocket square. You’re not an extra on Gossip Girl. Pick one or two fun accessories and stick to that.

Skills every prepster should master:

Social grace. Write thank-you notes, buy hostess gifts, be cordial to everyone, and stay classy in the presence of those who are not. Bad manners and cattiness are so unbecoming.

Tying a bow tie. It’s like riding a bicycle. You’d never imagine how many men came into Ralph Lauren [Van used to work at the Georgetown store] on the night of a big event in a tux with an untied bow tie and asked a salesperson to tie it for them.

Grooming products to pick up:

For men: unscented Dove soap, Marvis toothpaste, and Kiehl’s Silk Groom.

For women: An Aveda paddle brush, Fresh brown sugar scrub, and L’Oréal Voluminous mascara.

Monograms—do or don’t?

Do.

Lilly Pulitzer—do or don’t?

Do. Balance it with non-Lilly accessories.

Popped collars—do or don’t?

Depends. This really got overplayed a few years ago. It’s practical if you’re playing tennis or out on the boat—nobody likes a sunburned neck. But if you’re just doing it for show, it can look a little contrived.

Blogs to read:

Put This On, the Trad, the Love List, An Affordable Wardrobe, Off the Cuff DC, and Pretty Polished [a shopping blog Lauren runs with a friend].

Up-and-coming prepster brands you should be wearing:

Kiel James Patrick—whimsical, handmade accessories out of Rhode Island.

Sasha Lickle Designs—Floridian-style jewelry inspired by sea life and the beach.

Pierrepont Hicks
—An American brand with beautiful ties and bow ties.

Smathers & Branson—A Bethesda-based needlepoint belt company. You can even get a “life belt” custom made to match your personal interests.

Hugh and Crye—This Georgetown-based shirtmaker has slim cuts and great patterns. And we love our native DC designers!

The best hangouts in DC:

The bar at the Cosmos Club in Dupont. The building itself is incomparably beautiful. It has a very clubby, old-Washington feel. I love how you have to write up the tab yourself with a golf pencil.

Jetties, the sandwich shop in Foxhall. The sandwiches are the best in the city. I love the fresh carved turkey with either cranberry sauce or avocado spread and whole-grain mustard.

Other Georgetown/Glover Park favorites: Surfside and Town Hall.

The best vacation spots:

Palm Beach, Florida. It’s a winter spot that draws plenty of preppy East Coasters. It’s truly a paradise—beautiful weather, pristine beaches, palm trees. Everyone wears pastels 100 percent of the time.

Northern Michigan: The opposite of Palm Beach—everyone looks casual and laid-back. Think bathing suits, oversize polos, worn-in beach bags, colorful towels, and Patagonias.