Modern preppy style is often credited to the fictional likes of Blair Waldorf and the ladies of Constance Billard—but long before the beautiful terrors of the Upper East Side were clad in plaid (please read that in Kristen Wig’s Gossip Girl voice, thanks), popped collars and patterned ties planted their preppy roots at the Ivies. Northeastern fashion in the early to mid 1900s was inspired by the leisure activities often enjoyed by the upper class. Sportswear for polo, sailing, and rugby served as the base of preppy style inspo for men’s fashion. Equestrian detailing and nautical stripes were worn by the ladies, in addition to tailored skirt suits and wrap dresses. With the emergence of Brooks Brothers as an on-campus retailer, Ivy league schools like Harvard, Princeton and Yale became a place to get both a prestigious education and a great outfit.
In the last 100 years, the elements of preppy style have surprisingly changed very little. School uniforms are worn (and often despised) across the country and argyle is still prominently displayed in J. Crew windows. The appeal of preppy fashion is that it looks clean, intentionally styled and—above all—is not swayed by fleeting trend cycles. Preppy fashion is its own genre of classic, so by wearing it, you are, too.
One of the best parts about classic pieces is seeing how every generation chooses to style them. Alabama rush TikTok reaffirmed that southern prep and charm still thrives amongst a younger consumer, but there is a very different prep revival happening on the East Coast. Prep’s resurgence surprisingly stems from the logo-loving crowd that once declared themselves Supreme Hypebeasts.
On any given day, there is a long line of men in rugby shirts waiting to get into Aimé Leon Dore’s flagship store in New York City. Aimé Leon Dore (ALD for short) has brought back polos and blazers but instead of affiliating them with boating, they feature the logos of the Knicks and the Yankees. Prep has historically thrived on exclusivity, so it is no wonder ALD’s “limited drop” retail model (similar to Supreme’s) piques these shoppers’ interests.
While it may be hard to get your hands on a trending pair of preppy shoes, it is easy to incorporate the style’s classic elements into your everyday wardrobe. A high-quality polo can easily be purchased at any vintage store—and everyone looks good with a navy cable knit tied around their shoulders.
This year, I challenge you to ditch the fleeting micro-trends and give long-term prepster aesthetics a go instead. Whether you’re looking for street style inspo or something to wear to the stables, this style roundup is sure to put some prep in your step.
A well-fitted skirt suit is a great preppy essential to look for when you’re vintage shopping. The set can be matched with a classic heel, or something funky like Doc Martens if you dare to edge it up.
Tennis whites are a staple of preppy country club culture. Bring the polished look to your street style or the gym with a tennis skirt and a crisp white t-shirt.
Consider playing up a preppy collar and gingham print with bright boots and accessories for contrast.
This layered look encompasses all of the elements of traditional men’s prep, but looks fresh and modern with feminine elements like a mini Louis Vuitton bag.
This look is head-to-toe classic prep, from the V-neck sweater and long pleated skirt to the socks and loafers. Each of these outfit elements can be worn on their own for a less-preppy feel, but they look especially amazing when paired together.
The navy and white combination on this is fitted blazer and ruffled skirt combo is so chic. The color combination has nautical roots, but can be worn in any setting, while the blazer keeps it very Ivy League.
Taking a preppy basic (like this school uniform-style jumper) and layering it with a kitsch collar and bag adds a fun element of trend. This is the type of uniform makeover you’d see on Gossip Girl and be so jealous of.
Layering is key when nailing down a preppy look. This look has classic layering with socks and heels, but a bold stroke of modern layering with the leather harness over a crisp white button down. Prep school kids everywhere are shaking!