Your Preppy Style Guide

Love preppy style? You’re not alone—this classic clothing style is one of the most popular looks among both men and women. This preppy style guide covers everything you need to know about women's preppy clothing, including how to dress preppy from head to toe.

What Is Preppy Style?

One of the best things about preppy fashion is that it never goes out of style. The term “preppy” has roots in the classic East Coast prep school and Ivy League attire, and it has been going strong for decades. Preppy style first originated in New England during the 1910s, but gained popularity in the 1950s and 1960s as designers began picking up on the trend.

Today, preppy attire remains classic, polished and all-American. The style is heavily based around staple pieces such as button-down Oxford shirts, pullovers, shift dresses and pearl jewelry—perfect for wearing anytime, anywhere. Preppy styles also draws inspiration from nautical, equestrian and resort fashion.

How to Dress Preppy

Keep It Classic

Clean lines and crisp materials are the foundation of preppy style clothing. Build your wardrobe around staples like dark wash jeans, preppy t-shirts and structured outerwear.

A flattering tunic top paired with simple black leggings, flats and a statement necklace is really all you need to nail the preppy look at any time of the year. During warmer months, start with a pretty ruffle sleeve dress and accessorize with sandals and pearl earrings.

Layer Up

The key to successful layering is choosing tailored, structured pieces that will lay neatly over one another, without lumps of excess fabric. A preppy sweater layered over a button down chambray shirt is a perfect example of that classic, polished collegiate look.

Don’t forget to finish your layered look with a beautiful gold and pearl bauble necklace!

Play With Patterns

The beauty of preppy style is that it works just as well on a tropical beach as it does in an Ivy League classroom. The trick is to select lightweight breathable fabrics, relaxed silhouettes and fun prints.

Preppy dresses featuring bright colors and intricate patterns are the perfect way to embrace a vacation state of mind every day of the year. Look for structured tunic dresses and shift dresses to keep your look as preppy as possible.

Other quintessentially preppy patterns include navy and white stripes for a nautical-inspired style, and buffalo check for a cozy fall or winter look.

Add Some Pops of Color

Pastel colors and bold stripes are cornerstones of women's preppy style, but it’s important to ensure that you don’t go overboard. Remember, the goal is always to look polished!

For example, try layering a bright sweater cardigan over a basic tee. Keep the rest of your outfit simple with neutral flats or heels, skinny jeans and a pearl necklace. This look delivers just the right amount of fun, while still remaining classically preppy.

Carefully Select Your Accessories

Starting with a solid foundation of preppy clothes is important, but it’s equally essential to select the right accessories. Pearl jewelry is classy and chic—a must-have in any preppy wardrobe.

During the summer months, floppy sun hats and monogrammed baseball caps are staple accessories. Punch up the preppiness of any outfit with tortoise shell sunglasses and a beautiful crossbody purse.

Preppy style is timeless and flattering, and it isn’t going away anytime soon. Embrace this classic look by incorporating a few of these preppy women’s clothes and accessories into your wardrobe!