For most, the term “preppy” conjures visuals of tweed blazers, boat shoes, and argyle sweater vests, often worn by well-to-do New Englanders. The origins of the term derive from just that (“prep” meaning preparatory school), but the aesthetic’s evolution throughout the 20th and 21st centuries is among the more nuanced arcs, which raises the question: What is preppy style?
The term was born in the early 20th century and applied to wealthy students—mostly coming from old money—who were being groomed for Ivy League education. Unsurprisingly, this lent itself to a less-than-inclusive aesthetic that was begging to be subverted. By the time 1980 rolled around, the now-iconic humorous guidebook to the style type, The Official Preppy Handbook, was released. Its intentions leaned more toward ironic than informative, but it managed to spark a preppy craze that would create different offshoots for decades to come.
Among the more notable references is hip-hop fashion, which pivoted the prep movement from its WASP associations to a fresher look that has changed what we think of when we say “preppy.”
There are certain designers that will forever be intrinsically tied to preppy style; namely, Ralph Lauren and Tommy Hilfiger. However, in recent years, brands including Thom Browne and Noah are ushering in a new era of prep—one that speaks to skateboarders, the hip-hop scene, and street style. Now, preppy style is less about a uniform and more about individuality: plucking items that nod to this traditional way of dress, but applying them to your personal style. Ahead, check out 14 pieces that will help you learn just what preppy style is and how to implement it within your personal aesthetic.
The Boxy Crew
Tie this pullover around your shoulders for instant preppy style vibes that translate equally well to work from home and days out. Take a cue from Gigi Hadid and style your pullover with everything from jeans to athleisure.
The Rugby Shirt
Wear this striped rugby with a pair of slouchy jeans and high-top sneakers. Or, look to Kendall Jenner for inspiration. The supermodel and reality star paired a black and white rugby shirt with jeans, Birkenstocks, and sunglasses for a chic, off-duty look.
The Sweater Vest
What is preppy style without a fun sweater vest? This one would look especially great over a white tee, and you could even tone down the preppiness by wearing with oversized cargo pants. Or, go for the gold with a complementary tennis skirt.
The Tennis Skirt
One doesn’t need to play like Serena to take a style cue from center court. Embrace the tennis trend and style a preppy skirt with an oversized graphic tee.
The Linen Button Down
There’s a million ways to wear a crispy white button-down shirt—explore those looks with the versatility of this one by Misha Nonoo. We love it paired with a white tank and worn open or buttoned to the top and tucked into jeans with loafers, for a ’90s-inspired take on prep.
The Golf Pants
For the ultimate preppy style, pair these golf pants with a sweater vest, then drape a denim jacket across your shoulders. With a shorter crop, these trousers can work with everything from loafers to kitten heels.
The Boat Shoes
These boat shoes would make a statement with a plaid suit for fall. But actor Blake Lively has also worn her boat shoes in a more understated way—with white jeans and a striped tee.
The Classic White Sneaker
Not sure what preppy style is when it comes to footwear? Clean white sneakers always do the trick. Try wearing them in a more unexpected way by pairing with a floral dress and denim jacket.
The Cable Knit Sweater
The slouchy, cable-knit sweater adds a casual touch to a preppy look. We love it worn loose and off the shoulder, or more formal and tucked in.
The Argyle Sweater
Argyle will forever be a print du jour of the prep world. We love how Bella Hadid styled hers with an oversized puffer jacket and matching hat.
The Straw Tote
This straw bag from Zara is the perfect outdoor accessory. Straw bags have been having a major moment of late and brands from Marni to Chloé now offer their own takes. This version allows you to try the trend without breaking the bank.
The Straight Leg Jeans
These white jeans feel like an homage to Jackie O’s Americana style. As an ode to the first lady, pair the look with a starchy white tee and cardigan, and—if you’re feeling bold—wrap a scarf around your head.
The Cashmere Sweater Shell
A solid, neutral sweater shell can ground any outfit. Shells often have matching cardigans which offer a fun, easy way to add some warmth to the look.
The Tartan Wrap Skirt
This preppy tartan miniskirt is a great transitional piece to wear in between summer and autumn. Try it with knee-high riding boots and a button-down, or veer in a different direction and pair with a vintage tee and chunky, platform loafers.
