Women’s Preppy Style: What To Wear To Look Your Best in Prep


Do tailored blazers, plaid prints and collared shirts make your heart skip a beat? If so, there’s a chance you love women’s preppy style as much as we do. From the clean lines, crisp colors and never-fail staples, this collegiate-inspired style is here to stay. Are you looking to pepper your wardrobe with preppier pieces? We’ve got you covered with our guide on all things about this all-American aesthetic. 

What Is Women’s Preppy Style?

At its core, women’s preppy style is a trend originally influenced by Ivy League students. In the 1920s, children of America’s wealthiest families were primarily sent to private preparatory schools. The majority of these institutions held a dress code that included collared shirts, blazers and skirts. As their education continued, these undergrads brought the stylistics of their uniforms with them. In 1937, Life Magazine wrote an editorial about student life at Vassar College. Photos of girls adorned in tweed skirts, sweaters and saddle shoes spilled onto the pages of the magazine. This scholarly style was no longer confined to classrooms and campus quads. Preppy style brands Brooks Brothers and Ralph Lauren made this fashion craze accessible for women’s everyday wear.

Today’s preppy aesthetic has evolved from its origins and we are happy to say it is far more inclusive. Toss “The Official Preppy Handbook” aside and make women’s preppy style your own. Hallmarks of the trend include plaid prints, collared button downs, polo shirts, chinos and sweaters. If styling these pieces together is a bit overwhelming, feel free to mix and match. Add a bit of edge to your look by pairing a faux leather jacket with a tweed mini skirt. Take a page out of the literary-inspired dark academia trend by combining the best of prep with vintage finesse. Or, indulge in the normcore aesthetic and pop a few throwback silhouettes into your rotation.

If you need a little preppy outfit inspiration, set your sights upon the women who definitely wore it best. Blair Waldorf, Jacqueline Kennedy Onassis and Reese Witherspoon all get an A in our preppy style grade book. There’s no wrong way to add a pinch of prep to your style to make it your own.

Women’s Preppy Style Pieces You Must Add to Your Wardrobe

Now that you know the basics of women’s preppy style and its origins, let’s break it down starting with the pieces that are mandatory for building the perfect preppy outfit. This spring 2022 fashion trend highlights a resurgence of all things collegiate. Included are staples like cardigans and pullovers, varsity sweaters and rugby shirts. You should absolutely indulge in these items as you build your prepster wardrobe. Wondering what else to be on the lookout for? Here are a few more staples that will put even more prep in your step.

The Basic Blazer

If “Gossip Girl” taught us anything, it’s that a well-fitted blazer can instantly elevate your ensemble. From jeans and pants, to dresses and skirts, a blazer is the optimal women’s preppy style layering piece. While a tailored blazer is the best choice for work, an oversized boyfriend blazer works wonders for your weekend wardrobe. For the ultimate preppy outfit, choose a casual plaid-printed blazer to toss over your favorite crisp white tee. Balance out the proportions by reaching for slim or skinny jeans in a dark wash. Add a pair of casual sneakers and don’t forget the bold headband to take your prep to the next level. 

The Simple Sweater

Another cornerstone of the preppy aesthetic is the timeless sweater. Prepsters welcome this workhorse wonder in any iteration, from sweater vests to grandpa cardigans and the polished pullover. You’ll find all of these styles in any classic closet. Wondering how to wear a sweater vest in true women’s preppy style? Try one over a simple, Oxford button-down shirt and pair with slim-fit, ankle chinos. For another option, a dainty floral or women’s golf-inspired skirt will let the sun shine on your legs during the warmer months. Pair one with a matching cardigan set and add chunky soled, Mary Jane shoes. Harness your inner Cher Horowitz from “Clueless” and don knee-high socks. We are totally buggin’ over your perfectly put-together preppy outfit

The Classy Collared Shirt (And Shirtdresses)

Ladies, you can’t have a preppy aesthetic without a collared shirt or two in rotation. Wear a classic white button-down shirt loose and oversized as a summer swim cover-up. Or, tuck it into a pair of polka-dot printed pants and slip into flats. While polos and button-down Oxfords are synonymous with women’s preppy style, we encourage you to step outside the box. American-heritage vibes are also found in rugby shirts and crisp cotton shirt dresses. A shirt dress paired with boat shoes is an ultimate outfit option. For chiller days, add a cardigan. Before you head out the door, don’t forget a leather tote to carry your belongings. For that final touch, have your initials embossed on your tote. Preppy style and monogrammed details are a match made in style heaven. 

Women’s Preppy Style Bottoms To Keep In Abundance

When it comes to bottoms, leave your leggings at home. Instead, step out in style with preppy slim ankle pants or a patterned skirt. Jeans transcend genres and are very versatile, so be sure to keep a pair on hand to build your look. Curious how to wear wide-leg pants while dressing for this preppy aesthetic? It’s easy. Choose a cable-knit sweater and loosely front tuck it into the trousers or jeans. Whichever look you choose, you’ll always want to put your best foot forward. Any prepster will tell you that their go-to shoe is a quintessential penny loafer. Try updating this comfy classic by slipping on a shiny, patterned embellished pair. These shoes will sharpen up your laid-back look.

Dare To Add Flair To Your Women’s Preppy Style With Color And Print

Add a modern spin on your preppy style pairings by incorporating trending prints and colors. Neutrals like black, unbleached creams and toasted nut browns will partner effortlessly with bold, sun kissed hues of the season. Looking to integrate vivid and cheery pops into your preppy style? Reach for sunny yellows, grassy greens, washed corals and raspberry pink. Hyper-bright rainbow hues are another option if you want to take a walk on the wild side in your best preppy outfits. Red, fuchsia and cobalt blue are sure to liven up your look. Brighten up your wardrobe from your sweaters to your shoes with your favorite colors. 

Women’s preppy picks tend to be enduring in style. Shake things up by adding a punch of print. Instead of classic, symmetrical polka dots, go with brush strokes or perfectly imperfect dots. Swap out traditional plaid checks with a summery gingham or let dainty backyard florals flourish. Another prime print is stripes, of course. The preppy aesthetic isn’t complete without one, two or three sets of lines. You can’t go wrong with a striped sweater or tee during the weekend. Partnering bold prints and bright colors? That’s how you ace a proper preppy look.

Ready to work preppy like a pro? Take your style quiz, order a Fix and ask your stylist to include classic pieces that will give you the Northeast-inspired wardrobe of your dreams. Buy what you like and send back the rest. Or, head over to Stitch Fix Freestyle™ to instantly buy items curated for your style and size. Shipping and returns are always free. It’s as simple as that.

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