Preppy clothing is considered a conservative, tailored way of dressing, while its urban counterparts are a little edgier, with comfort at the forefront. Urban clothing gets its vibe from street culture — graphic T-shirts, cargo shorts and jeans that are over-size, elongated and colorful. Preppy, on the other hand, takes its cue from academia and business — nicely tailored jackets, crisp Oxfords and pristine loafers round out the preppy wardrobe. Young and mature woman can wear both styles with ease. The key is to blend in some trends to make a fresh twist on either look.


Pants and Shorts

Freshly pressed chino pants, nicely tailored jeans and Bermuda shorts are all preppy wardrobe staples. Fruity colors such as tangerine, lemon, peach and honeydew brighten up a summer outing, while tan, navy, black and red are in line with the darker days of winter. Capri pants, straight-legged khakis that fall at the ankle and flat-front shorts to the knee represent a conservative style in seersucker, madras and gingham. Urban pants and shorts, however, are not quite as tailored, may hang loosely below the knee or ride a little higher on the thigh. In urban style, plenty of pockets and zippers are found on jeans, colored denim, cargo shorts and sweat pants. These are looser styling options that put comfort at the forefront.

Tops and Jackets

Preppy tops include short-sleeved knit polo shirts, pressed Oxford cloth shirts, and sleeveless tops and blouses with a collar bow or ruffles down the front. Pair these with a well-fitted trench or pea coat, a sweater twin set, corduroy blazer or a woolen pull-over sweater in a check or argyle print. On the other spectrum is urban style, with its butterfly-winged blouses, loose-fitting vintage T-shirts, tank tops and peasant-style tops. Soft materials and flowy fabrics embody urban comfort in a variety of cotton blends, silks, gauze and linen. Pair these urban offerings with a slouchy cardigan sweater, off-the-shoulder sweatshirt, bomber jacket with metal embellishments or a jean jacket.

Dresses and Skirts

Preppy dress staples include the sheath dress with polka dots, a hot pink-and-lime printed halter dress and a shift dress with a boat neck. Worn at work or while lunching at the country club, these dress options have you looking and feeling confident and smart. Seersucker, madras and printed fabrics with little turtles, palm trees and anchors all look good on an above-the-knee straight or A-line skirt. Urban style dresses include the flowy maxi dress, a peasant-style skirt with tiered ruffles and a denim jean miniskirt. A touch of romantic whimsy, such as cascading fabric, loosely tied bows, animal prints, color blocks and soft floral prints round out the urban woman’s wardrobe.

Shoes and Accessories

Preppy shoes include loafers, riding boots, ballet flats and peep-toe kitten heels. In the summer, choose a nude-colored shoe that blends with your skin tone to create a seamless look. Come winter, add a pair of textured hose beneath skirts and dresses for body warmth and fashionable interest. Crests, sailboats, palm trees and emblems of all kinds are found on preppy clothing. Traditional wardrobe accessories include a canvas belt, silk scarf, large sunglasses and a straw hat. Pearls and diamonds complete the preppy outfit. For the ultimate urban look, wear boots with hardware, athletic shoes, wedge sneakers, thin-soled canvas tennis shoes with stripes or sandals with large buckles. A chunky watch, rope belt, colorful hoop earrings, knit cap and a hobo tote are all accessories that complete the urban-style outfit.