When you think of preppy style, what comes to mind? Boat shoes? Nautical stripes? Princess Diana at a polo match?
Whichever image you can conjure, keep it close at hand—because the collegiate-inspired aesthetic is officially making yet another a comeback. But while we respect the classics, we're also craving fresh, new ways to redefine the all-American attire.
Ahead, we share a brief history of preppy style for women and dish out advice on how to wear it with a modern edge.
A brief history of preppy style
Peruse any vintage Brooks Brothers catalog and you'll quickly see that preppy style's roots trace all the way back to the American sportswear genesis of the late 1940s. But it's most commonly associated with the prep-school-to-Ivy League pipeline.
Coinciding with an increasing female attendance at prestigious universities in the 1950s, publications like "Vogue" and "Life" began to feed young women exemplars of collegiate dressing. (Katharine Hepburn in a three-piece suit and oxfords? Iconic.) Fast-forward to the 1980s when a legion of preppy youth emerged after the release of Lisa Birnbach's "The Official Preppy Handbook." Though the guide outlined the nuances of preppy style with a tongue-in-cheek humor, Birnbach was still responsible for a boom in sales of pastel pique polos and the rise of L.L.Bean.
What does preppy style look like today?
Women's preppy style is devoted to crisp, clean, and considered staples that walk the line between casual and sophisticated. It's more tailored blazer than moto jacket, more chinos than distressed denim. But it's not without personality—throwing a bold accessory or whimsical pattern into the mix takes it to the next level.
Preppy style women
Rocking this aesthetic with aplomb is easiest when you have stylish examples to follow. Here are a few of our favorites.
Like her mother-in-law—or a young Jackie O.—Middleton has graced many a best-dressed list for her prim sartorial moments. We swoon over the Duchess of Cambridge in floral fit-and-flare frocks with sensible, pointy pumps—and she's no stranger to dark-wash jeans and a candy-colored cashmere coat.
The goddess of contemporary workwear rewrote the rules of "office-appropriate" during her stint as creative director and president for J. Crew. She took the staleness out of our conference-room ensembles with clashes of stripes and leopard print, sequins and denim, cashmere and jacquard.
Lyn Paolo, costume designer for TV show "Scandal," envisioned a wardrobe for the genius DC lawyer based on conservative high-fashion choices. Tinged with preppy notes, Olivia Pope became an accidental style icon for her structured handbags, plaid capelets, and sparkling single-strand necklaces.
Tips for dressing preppy
The new rules in building a preppy outfit for women require an unconventional approach with traditional choices to anchor it. Try more to look like you pulled your pieces off a Ralph Lauren mannequin rather than dove head first into Dionne Davenport's closet.
Start with colors like navy, brown, beige, and white as your base, then incorporate feel-good hues (e.g., pastel pink, bright orange) to inject some cheer.
Preppy style is known for its layering combinations, so be sure to layer up whenever possible. This is your opportunity to play with a pattern (or two).
Accessorize, accessorize, accessorize—we can't say it enough. Go old-school with a strand of pearls and pumps, or flip tradition with platform boat shoes.
How to build your preppy outfit
Break it down into these steps, and you'll find it's a breeze to master women's preppy style.
1. Find your base
You can't go wrong with a collared shirt—seek out a solid color or experiment with a charming print.
Polo dresses embody the sporty influence within the preppy dress code. (Bonus points for monogramming.)
Knitwear is a common theme throughout the preppy aesthetic, which makes a short-sleeve sweater a no-brainer.
The shirtdress is an essential piece you can dress up or down, transitioning seamlessly from day to night.
2. Time to coordinate
A shot of color by way of cute shorts brings the whimsy to a preppy summer getup.
Purists may balk at the thought, but well-cut joggers are unexpected and capture the subtle irreverence of prep.
Some say denim has no place in preppy style, but slim jeans in a dark wash will fit in nicely.
Fun and feminine, opt for a pencil skirt with an eye-catching print, splashes of color, or both.
3. Add another layer
Preppy style is all about layering, so throw on a varsity-inspired pullover with stripes.
A patterned blazer checks all of the preppy aesthetic's boxes—polished, smart, and timeless.
Layer a sweater tank or wear it solo—even better if it comes in a fun pattern.
Let your trench's belt hang loose to show off your dress underneath, or cinch it with a contrasting one.
4. Put the prep in your step
It's de rigueur for preppies to slip into boat shoes. After all, they go with pretty much everything and epitomize smart casual.
The details are what make a pump preppy, so opt for polka dots, block heels, and round toes.
Oxfords or loafers:
Decidedly dapper, oxfords and loafers are dressier than boat shoes but light years comfier than heels.
An icon in the oeuvre of American sportswear, simple sneakers give a toned-down feel.
5. Add accessories to bring it all together
Whether a tote or satchel, make the move to carry a structured bag in a bold shade.
Leather strap watch:
Stick to a minimalist timepiece defined by clean lines and an unfussy face for just a touch of shine.
Contemporary pearl jewelry is cool and refined, so leave your beloved grandmother's pearls in the box.