What Is Preppy Style? 14 Pieces That Modernize the Classic Look

The iconic aesthetic has come a long way.

What Is Preppy Style Ella Emhoff

@ellaemhoff/Unsplash

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 this phrase 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 begs the question: what is preppy style? 

As mentioned, this term was born in the early 20th century and given to those 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 many decades to come. Among the more notable references is hip-hop fashion, which pivoted the prep movement from its WASP associations to a fresh aesthetic that has remolded 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 like 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 translating them to a modern wardrobe. Ahead, see 14 pieces that help you learn just what preppy style is and how to implement it within your personal aesthetic.

Tkees The Boxy Crew
Tkees The Boxy Crew $110
Shop

Tie this pullover around your shoulders for instant preppy style vibes that translate equally well to work from home and days out.

Kule The Rugby
Kule The Rugby $98
Shop

Wear this striped rugby with a pair of slouchy jeans and high-top sneakers.

Rowing Blazers Racquets Sweater Vest
Rowing Blazers Racquets Sweater Vest $195
Shop

What is preppy style without a fun sweater vest? This one would look especially great over a white tee.

EleVen by Venus Williams Flutter Skirt
EleVen by Venus Williams Flutter Skirt $84
Shop

Embrace the tennis trend and style a preppy skirt with an oversized graphic tee.

Misha Nonoo Husband Shirt Linen
Misha Nonoo Husband Shirt Linen $185
Shop

There’s a million ways to wear a crispy white button-down shirt—explore those looks with the versatility of this option.

Tory Sport Tech Twill Golf Pants
Tory Sport Tech Twill Golf Pants $188
Shop

For the ultimate preppy style, style these golf pants with a sweater vest, then drape a jean jacket across your shoulders.

Sperry Authentic Original Boat Shoe
Sperry Authentic Original Boat Shoe $95
Shop

These boat shoes would make a statement with a plaid suit for fall.

Jack Erwin Holly Tournament Sneaker
Jack Erwin Holly Tournament Sneaker $165
Shop

Not sure what preppy style is when it comes to footwear? Clean white sneakers always do the trick.

Polo Ralph Lauren Cable-Knit Cricket Sweater
Polo Ralph Lauren Cable-Knit Cricket Sweater $268 $190
Shop

The slouchy, cable-knit sweater is a one-way street to preppy style.

Khaite Noelle Argyle Wool Sweater
Khaite Noelle Argyle Wool Sweater $860
Shop

Argyle will forever be a print du jour of the prep world.

Vineyard Vines Striped Straw Market Tote
Vineyard Vines Striped Straw Market Tote $128
Shop

This straw bag from preppy style haven Vineyard Vines is the perfect outdoor accessory.

Favorite Daughter The Mischa Straight Leg
Favorite Daughter The Mischa Straight Leg $198
Shop

These white jeans feel like an homage to Jackie O’s Americana style.

J.Crew Cashmere Crewneck Sweater Shell
J.Crew Cashmere Crewneck Sweater Shell $95
Shop

A solid, neutral sweater shell can ground any outfit, no matter what preppy style is to you.

Cider Green and Red Tartan Wrap Skirt
Cider Green and Red Tartan Wrap Skirt $26
Shop

This preppy tartan miniskirt is a great transitional piece to wear in between summer and autumn.

Related Stories