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. In 2021, 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.
Tie this pullover around your shoulders for instant preppy style vibes that translate equally well to work from home and days out.
Wear this striped rugby with a pair of slouchy jeans and high-top sneakers.
What is preppy style without a fun sweater vest? This one would look especially great over a white tee.
Embrace the tennis trend and style a preppy skirt with an oversized graphic tee.
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.
For the ultimate preppy style, style these golf pants with a sweater vest, then drape a jean jacket across your shoulders.
These boat shoes would make a statement with a plaid suit for fall.
Not sure what preppy style is when it comes to footwear? Clean white sneakers always do the trick.
The slouchy, cable-knit sweater adds a casual touch to a preppy look.
Argyle will forever be a print du jour of the prep world.
This straw bag from the prepster-beloved Vineyard Vines is the perfect outdoor accessory.
These white jeans feel like an homage to Jackie O’s Americana style.
A solid, neutral sweater shell can ground any outfit.
This preppy tartan miniskirt is a great transitional piece to wear in between summer and autumn.