Style Breakdown: What is the Preppy Style?

Proper, minus the rigidity.
preppy style

You know what they say: a crisp white button-down is a wardrobe staple—but it is also the piece that a preppy look builds upon. If you’re a telephile, you would perceive it as the Blair Waldorf look or Cher in Clueless; but what about the style is so fascinating that it has lasted decade after decade? You might be seeing headlines saying, “Prep is back!” but the truth is, preppy never left. 

The style has lingered around long enough because it revolved around the idea of being balanced. There’s a balance between casual and formality, a balance between neutral and vivid colours, and a balance between structured and soft silhouettes. It has a bit of everything in a harmonious way and omits the restrictions, be it the occasion, age, body shape, or even gender. The history of it, however, is not as inclusive as it is today. In fact, it was deeply rooted in social segregation.

The Academia Cousins

Before we delve into its history, we must first clear the air. Often used interchangeably, Ivy, like Preppy, has academic roots too. The difference might be minute but from a class angle, the Ivy style was popular among students from prestigious schools, wealthy or not. Preppy, on the other hand, depicts a lifestyle entangled with multigenerational wealth background. To put it simply, Ivy is more proper and conservative and the latter is a derivative that adds casual to the serious.

The casualness reflects how young adults from upper-class backgrounds spend their leisure time playing tennis, polo, lacrosse, sailing, or hunting. Some common pairing includes structured blazers with polo shirts; ties with tennis skirts, or baseball caps with cardigans. Some would even add on nautical elements like anchors or whales.   

View this post on Instagram

A post shared by Lady Diana, Princess of Wales (@lady.diana._)

The Preppy style we have in mind inclines towards the New England style. The rich, however, dressed and acted differently based on their geographical location. The Southern Preppy style usually incorporates vibrant colours and prints that contrast each other. Sloane Ranger from the UK, for example, is the equivalent of Preppy—think Lady Diana.

Preppy, Then

Preppy is a status-indicative style traced all the way back to the 1990s. Young lads from silver-spoon upbringing would dress for preparatory schools, preferably ending up in Ivy Leagues—hence the name. They took cues from English uniforms: button-down with a knitted jumper (draped over your shoulders) and a pair of tasselled loafers. Their female counterparts began adopting the look later in the 1930s. 

View this post on Instagram

A post shared by 𝗕𝗹𝗮𝗶𝗿 𝗪𝗮𝗹𝗱𝗼𝗿𝗳 (@blairwaldorfs)

The preppy style, however, really peaked in the 1980s thanks to the release of the tongue-in-cheek The Official Preppy Handbook. The satirical book became a guideline (ironically), giving readers a glimpse into the life of real preppy elitists. It ranged from how to decorate their houses to what pets they would keep, and of course, the way they dressed. From the hats, shirts, cardigans, loafers or hunting boots, L. L Bean dominated the Preppy wardrobes. The key: sustainable pieces with top-notch quality that lasts the wear and tear. In this case, The Official Preppy Handbook stated that young preps were often seen wearing hand-me-downs from either their brothers or mothers. 

View this post on Instagram

A post shared by Vintage Preppy Clothes (@vintagepreppyclothes)

Once meant for the WASPs (White Anglo-Saxon Protestants), it gained popularity among the masses in the 1980s, regardless of whether they attended prestigious Ivies. Eventually, the handbook with parodied yet useful tips democratised the style successfully. The style became a quintessential American look throughout the decade. What entailed was that Preppy attire was no longer hard to pull off since the path leads to commercial brands like Lacoste, Calvin Klein, J.Crew, and Tommy Hilfiger in the following decades. 

Preppy, Now

Preppy does has an image of a relic from a bygone age often associated with an obsolete social status connotation. Retrospectively, however, the resurgence in the 80s was a counterculture response after the 1970s. It’s only reasonable to see it return stronger than ever in recent years, given the unstable socioeconomic state. As we recoup from a series of turbulence, the staggering resemblance to the 80s is unmistakeable.

View this post on Instagram

A post shared by Gossip Girl (@gossipgirl)

Inevitably, Preppy coming back is also an antithesis to street styles that took over the fashion industry in a sweeping manner back in the 2010s. The wave of nostalgia hitting the television screens too, has once again brought the golden age of Preppy back into the light. A reboot of Gossip Girl, for example, racked up the sale of tweed suit sets and shirts, and eventually assisted Ralph Lauren to slough off their “grandpa vibes” to be cool again. The obsession with “old money” and stealth wealth on the Internet, or the quiet luxury that surfaced and reached eventually reached mainstream attention following the highly rated HBO series “Succession”, had also hammered up the public’s fascination for a lifestyle of the riches.

The ideology behind the style has certainly evolved but the look itself was passed down the generations without major changes. It has gone beyond the campus, onto the streets, and eventually strutting the runways—back-to-school looks are more progressive now. Some of the maestros like Thom Browne, Gucci, Miu Miu, and Prada, just to name a few, make preppy evergreen in high fashion. Newcomers like Shushu/Tong, Wales Bonner, Aimé Leon Dore, and Ami Paris are giving the Preppy a fresh take.

Read more: In Fashion, Beach Clubs are Still Big Business

Ultimately, it leans more towards the laidback yet poised attitude of the wearer instead of focusing on what and what not to put together. Today’s Preppy style slices up the haughtiness, exploring and balancing the juxtaposition in a subverting manner. It is deconstructed and reconstructed, and while the tailored fit is still very much appreciated, “ill-fitting” too, is equally as welcome. Whether it’s sizing down like Miu Miu’s micro miniskirts or blowing it up like the inflated Prada loafers, rules are meant to be broken. While embracing the collegiate cues, it also challenges the once-gendered style. People of all ages and walks of life are entitled to bring forth the greenhorns and naivety in us.