The 10 Preppiest Fashion Labels

By  May 27, 2008

Long before Ralph, Tommy, and Tory dabbled in country club-chic, brands all along the Eastern seaboard pioneered—and perfected—distinctive preppy styles. In honor of summer’s arrival—and with it, many picturesque clambakes, tennis matches, and polo games—we pay homage to iconic blue-blood brands. So before you board the puddle-jumper or pour yourself a T&T, take cues from this short-list when planning your preppy summer wardrobe:

Lilly Pulitzer

lilly pulitzer
Jackie Kennedy—the patron saint of all-American style—was one of the first lady-like tastemakers to sport Lilly Pulitzer‘s distinctive, patterned frocks. (The former First Lady and the designer were class-mates at the Chapin school in Manhattan’s Upper East Side.) Since the Palm Beach-based label’s inception in the late ‘60s, many of Jackie O’s fans (and really, who isn’t one!?!) have followed suit.

Stubbs & Wootton

stubbs and wooton
A favorite all along the Eastern Seaboard from Palm Beach (where the label got its start) to Newport, Stubbs & Wootton slip-ons are a staple of upper-crust attire.


Emilio Pucci

emilio pucci
A favorite of the pearl-wearing set, Pucci‘s swirling prints have been hostess-attire since the 1960s, when hostess-with-the-mostesses like C.Z.Guest and Babe Paley began sporting the Italian house’s signature frocks.


Vera Bradley

vera bradley
Vera Bradley‘s quilted duffel bags are a frequent fixture on Nantucket ferries, Palm Beach puddle-jumpers, and Newport sidewalks. Fortunately for us, these cheery satchels–priced between $50 and $150–don’t require trust funds to purchase.


Sperry Topsider

sperry topsider
Whether on or off the water, the yachting crowd often opts for the sweet, starboard-ready boat shoes from Sperry Topsider.


CK Bradley

ck bradley
Founded in 1999 by young Manhattanite Camilla Bradley (then a student at the prestigious Trinity school) CK Bradley features a candy-colored assortment of cheekily-printed belts, headbands, and more Blair Waldorf-worthy accessories.


David Yurman

David Yurman
Those that think of “summer” as a verb prefer the sophisticated, yet simple designs of David Yurman. The jeweler’s signature twist and buckle-accented baubles complement both private school wardrobes and doyenne dress.


Kenneth Jay Lane

kenneth jay lane
Coral pendants, colorful enamel, and charming aquatic animals are key motifs in Kenneth Jay Lane‘s cheap’n'chic baubles. (Because the diamond tennis bracelet can be so gauche to wear non-stop in the summer.)



LL Bean

A must-have from Cape Cod shores to South Hampton greens, monogram-ready totes from Maine’s L.L.Bean label appeal to those whose surname comes with stately roman numerals.


Vineyard Vines

Vineyard Vines
Founded by former investment bankers, brothers Shep & Ian Murray, Vineyard Vines takes its name and aesthetic inspiration—think seersucker shorts, patchwork skirts, and ribbon belts—from the tony vacation hot-spot, Martha’s Vineyard.