Preppy Style Fashions for Women

Yelena Johnson
Woman in denim shirt and striped t-shirt

If you love to rock a preppy look, you are not alone. These fashions can take a girl from daytime to nighttime, and from super casual clothes to formal wear. How you wear a preppy style will vary with the season. Spring and summer clothing favors bolder colors and florals, while fall and winter wear is all about neutrals, layering, gingham and plaid. Follow these seasonal guides to preppy dressing to get the look.

Spring and Summer Preppy Attire

Whether you are heading to do a school drop-off or a day at the races, preppy dressing is always about well-tailored basics.

Ideas for Casual Outfits

  • Start your casual preppy outfit with a fitted button-down poplin shirt with rolled-up sleeves in a spring or summer color (try pink or peach, and tuck in your shirt to up the prep factor).
  • Woman in preppy casual clothes
    Wear well-fitting capri jeans or colorful chinos on the bottom. If the weather is warmer, consider choosing a pair of patterned cotton shorts instead. To dress it up a bit more, consider a simple cotton skirt that hits mid-thigh.
  • A pair of ballet flats in colored leather will complete the look. Choose true ballet style flats with a feminine bow on the front, or a cap toe ballet flat. For days when you are running around town, consider wearing nicer sneakers such as Jack Purcell's, Supergas or patterned Keds.
  • For jewelry, layered pearls and gold monogram necklaces are the quintessentially preppy choice. For your wrist, think nautical chic with a rope knot bracelet. Try not to layer multiple types of necklaces - a few pearl strands look great together, or a few rhinestone necklaces layered together can be a bold accessory, but do not mix and match the types of necklaces since that lends itself more to a boho look than a preppy vibe.

Dressy Warm-Weather Looks

  • Since it's such a perfect preppy pick, a button-down shirt can also be dressed up for a more formal preppy outfit. Just be sure to pick a more formal fabric - either a nice quality linen, a silk blend, or a high-thread cotton. Sleeves can be either folded up (more tailored looking than a rolled sleeve) or kept long and buttoned at the wrist.
  • Sheath dress
    Two styles of skirts lend themselves particularly well to the preppy look: a knee-length a-line skirt (preferably in a silk fabric for more dressy occasions) and a fitted pencil skirt. Tuck your shirt inside the skirt, and make sure the skirt hits at the natural waistline for the most preppy, flattering fit. Consider choosing a skirt in a bold, bright color or preppy floral print - spring and summer prep wear encompasses lots of florals and bold, happy hues.
  • If you are seeking a preppy dress instead of a skirt and shirt combination, consider looking at a v-neck, scoop-neck or boat-neck style sleeveless a-line dress that hits slightly above the knee. This style of dress is the epitome of country-club chic, and it also looks great in bold floral patterns or even nautical navy and white stripes. For chilly nights, pair your dress with a button down cardigan sweater in a complementary color.
  • For shoes, a pair of ladylike pumps make a great choice. Extra bonus points for choosing a pair with a detail like a bejeweled bow or a classy pattern on the fabric.
  • Accessorize with a simple clutch and, of course, a layered pearl necklace. A layered pearl necklace is an excellent accessory because it pairs just as well with casual clothing as it does with dressy outfits. Put it on in the morning, and wear it from day into night.

Fall and Winter Preppy Clothing

When the leaves begin to change and the temperatures dip, preppy clothing moves from bolder hues and prints into neutral tones and subdued, classic prints. Khaki, navy, gray, hunter green, browns and maroon are the quintessential fall colors for this fashion style. Fall prints include plaid, gingham, herringbone and the year-round preppy taskmaster, the nautical stripe.

Casual Clothing for Fall and Winter

  • As with Spring and Summer, you can't go wrong beginning your outfit with a basic button-down shirt. To keep it seasonally appropriate, choose a plaid or gingham print shirt in a fall color.
  • Cable knit sweater
    Layering is a must-do for your fall look. Cable-knit sweaters and button-down long cardigans are ideal layering choices over a fitted shirt. Push up the sleeves on your sweater for a three-quarter length look, and roll the button-down's sleeves up to meet the sweater to accentuate the layering effect. Be sure to pull the collar of the button-down through the top of the sweater opening so the collar of your shift lies on top of the sweater collar.
  • Another great layering option is a quilted vest. Vests can either go directly on top of the button-down or on top of the sweater and shirt for cooler days when more layers are necessary. Choose basic fall color for the vest like navy or charcoal gray, which will work with almost any other autumn preppy item in your wardrobe.
  • In early fall, ankle or capri-length jeans or neutral fitted pants look great paired with button-downs and sweaters. As the weather gets colder, swap out your ankle-length pants for long pants that can be tucked into tall boots.
  • For a casual dress, pick up a knee-length button down shirtdress. Pair it with a polished leather belt or nautical rope belt and flat tall boots.
  • Fall and winter footwear varies on how cold the temperatures are. Enter the fall season wearing ballet flats in hunter green or navy or the same summer sneakers mentioned above. As the leaves fall off the trees and sweater season officially begins, move to tall riding boots in a Ralph Lauren style, or the prepster favorite, Hunter rain boots. Hunter rain boots look best when a tall knit sock is peeking out from over the top of the boot.
  • Once winter arrives, add a coat over your bottom layers to keep out the chill. Classic preppy coat styles include wool single and double breasted coats. Look for one that has either toggle clasps or gold buttons to amp up the look.
  • Another fall classic is the blazer. A schoolboy blazer with an upturned collar just oozes prep, and a corduroy version is a bit more casual.
  • Burberry style trench coat
    If a wool coat is too warm for your locale (Los Angeles and Florida, for example) consider a lightweight quilted or patterned puff jacket that fits snug to the body. Another classic option is a lightweight khaki colored trench coat, such as the eponymous Burberry trench. You will still look preppy without overheating in wool.
  • For another layer of warmth, try adding a fluffy preppy scarf to the mix. Scarves are versatile since they can be worn with almost any combination of autumn preppy wear -- they look just as great paired with a button down, pants and ballet flats as they do layered over an overcoat, thick pants and knee-high boots.

Dressy Fashions for Colder Weather

With winter comes galas, balls and holiday parties - the perfect time to bust out your preppy party frocks and pearl necklaces.

Woman wearing red checkered preppy dress
  • Knee-length and mid-thigh dresses are a good choice for cocktail hours and more casual holiday parties. As with spring and summer dresses, choose cuts that are simple and classic for preppy appeal. You can also add a bit of volume to your dress with a peplum skirt detail. A-line dresses are another great selection for cocktail parties and date night, along with sheath dresses.
  • Simple silhouettes in preppy prints are another great dressy option. A plaid dress or a herringbone print dress are stylish options that fit right in with this type of wardrobe.
  • If you are wearing a shorter dress, keep your legs warm with plaid print leggings or tights. They work well layered beneath high heel boots and keep you warm in the evening as well.
  • For a fancy affair such as a black tie gala, choose a long navy striped ballgown with a nautical nod to prep. If you can't get enough of bold colors, choose a simple silhouetted gown with color blocking.
  • Channel the preppy basic, the button-down shirt, for your formalwear. A formal silk shirt and ballgown combination dress is a stunning look that has preppy roots.
  • Don't forget to accessorize your dressy outfit with plaid high heels and plenty of pearls. Choosing fall-inspired materials like suede in stiletto pumps is a great seasonal pick.
  • For chilly formal nights, layering your wool double or single-breasted coat over a dress is just fine. Or, opt for lighter coverage with a cashmere cardigan - perhaps one with a jeweled neckline to dress it up.

Building a Preppy Wardrob

Happy couple on a shopping spree

The general guidelines for dressing preppy include wearing basic, well-fitted (not too loose, not too tight) staples in neutral colors as well as simple prints like stripes, plaid and florals. Create outfits with an event or theme in mind, which makes it easier to narrow down your options and choose the right pieces. Designers who are known for their preppy clothing collections include J. Crew, Ralph Lauren, Oscar de la Renta, Tommy Hilfiger, La Coste, and Banana Republic. Checking online images after each season's Fashion Week is a great way to stay up-to-date on your wardrobe inspiration.

If you are aiming to build an entire preppy wardrobe from scratch, focus on seasonal selections broken down into spring/summer and fall/winter as with our guide above. Bold, bright hues and floral patterns in simple silhouettes are just right for spring and summer, while dark hues and neutral colors including cream, black, gray, navy and camel are a dream for fall dressing. Patterns to focus on for your fall and winter preppy wardrobe include herringbone, plaid and the perennial favorite, nautical stripes. With a little planning and patience, creating the perfect preppy wardrobe is a piece of cake.

Preppy Style Fashions for Women