Demystifying the Post-Preppy Aesthetic

Francesco Daprile
8 min readMay 12, 2021


Franco Raggi, “La Tenda Rossa” (1974)

Sometime around 1954, Miles Davis walked into the Andover Shop — the quintessential go-to destination for Ivy Leaguers — and single-handedly turned the world of style upside down. A year later, when Davis appeared onstage at Newport Jazz Festival in a flamboyant seersucker sack coat, rounded club-collar shirt and bow tie, two very separate worlds instantly clashed — those of the establishment and the black jazz culture of the time — resulting in “a crashing chord of cool that obliterated the line between square and hip, sounding a fashion fortissimo that lasted several years before fading into the silence of pop-culture obscurity¹”.

Miles’ adoption of the Ivy look wasn’t a spur-of-the-moment inspiration, but rather a strategy that he’d been working on since the start of his career when he was catching hell from Dexter Gordon who essentially accused him of not dressing “Black” enough². Championing the unlikely pairing of African American artistry and WASP style, Davis’ Ivy Cool suddenly became the cliche uniform at jazz festivals in Monterey and Newport, creating a new idiom of cool that was quickly absorbed by the West Coast Jazz entourage and — most remarkably — helping set the stage for the civil rights marches and demands for equality that came a decade later.

Clothes, it appears, are more than just fabric on a hanger: they’re a key to locked doors and can be used strategically. The wearing of an item of clothing is fundamentally an act of meaning that goes beyond modesty, ornamentation and protection. It is an act of signification and therefore a profoundly social act right at the very heart of the dialectic of society³. In this sense, fashion is a cultural object capable of constituting complex systems of communication and therefore of meaning so that when using the expression “preppy”, we are necessarily creating a link of equivalence between a concept (preppy) and a form (a particular garment or object).

In this regard, Trubetskoy appoints the “linguistic nature of clothing⁴” according to which the binary juxtaposition of dressing/dress form a system in which the former identify the individual dimension of an item of clothing (e.g. its degree of dirtiness) while the latter works as an “institution” — something that transcending the individual dimension becomes cemented in ritualised forms and social practices. “Dressing” can, and certainly does influence “dress” and the relationship between the two is in a constant state of negotiation: Miles’ “dressing” later became the “dress” of the 60s Hard-Bop scene, with the likes of the public and other Jazz greats as beautifully documented by Jim Marshall’s book Jazz Festival.

The eight private colleges that are members of the Ivy League athletic conference may be for just a selected few, but the clothes and styles popularised on their campuses have been slowly democratised into staples of classic American style. Traces of this popularisation can even be found in the Oxford Dictionary’s definition of “preppy”: “A preppy is a young person who goes or went to an expensive private school and who dresses and acts in a way that is thought to be typical of such a school”. According to the definition, it appears, preppy is not only a bourgeois condition of privileged young kids attending private school, but also some sort of “costume” of those people who “acts and dress in a way that is thought to be typical of such a school”. The definition suggests that the status of “preppy” is no longer exiled in the academic space, but through “clothes and acts” has transcended the college making its way to popular culture.

Initially the uniform of the Eastern Establishment and WAPs in the 1930s, the Preppy Look originally reflected a contingent reality: the one inside Ivy League colleges. During the 60s, the slavish admiration Japan had towards American fashion, and more specifically Ivy fashion, led a group of enthusiasts and clothiers to fly to the US to document students’ life and clothes in campuses; the field trip culminated with the publication of the legendary book “Take Ivy”. Among the aforementioned group of enthusiasts there was a clothier named Kensuke Ishizu whose brand “VAN” promoted, manufactured and sold Ivy, earning the likes of a small crowd of aficionados: the Miyuki Tribe. In 1964, in occasion of the Summer Olympics, Ishizu was invited by the Olympic Committee to design the uniform for the Japanese team. Here, he came up with the idea of a flamboyant bright red blazer with gold buttons and white trousers that resembled the Traditional Ivy Leaguers uniform. When the Japanese team showed up at the ceremony, an idealised version of American fashion was officially cemented into a national sport uniform and catered to a global audience. The “Preppy Look” had become a “costume”.

This event marks the beginning of a process of cultural appropriation that peaked in the 90s with the commodification of the “Preppy Look” by lifestyle brands like Polo Ralph Lauren or J. Crew that leveraged its aesthetic appeal to build their own commercial narrative. Detached from its original reality — through cultural appropriation and commercial remix — the Preppy subculture was incorporated, manufactured and packaged for commercial interests, ultimately becoming a style cue at the disposal of anyone.

As America slipped into a more libertine vestimentary code, the original ethos of the Ivy League irremediably evaporated leaving us only its vacuous aesthetic footprint. Today, bearing no relation to any contingent reality whatsoever, the modern preppy culture has become its media images and cultural myths more so than it is a real, material subculture. Think about Noah or Rowing Blazers postmodern pastiche of Ivy/Preppy fashion.

The term pastiche is derived from the Italian word pasticcio, which refers to a combination of elements that evokes assemblage, collage, montage, capriccio (a composing style that combines elements from different places), medley forms, and hip-hop sampling, scratching, and riffing⁵. Pastiche has a very peculiar relationship to history. As a strategy, it can often involve pilfering from history and combining — through quoting and mash-ups — historical elements in ways that empty the signifiers of historical meaning combining them in (sometimes mismatched) fragments of style⁶ — Ever heard of Virgil Abloh?

Pastiche rarely intends to make a statement about the historical eras or texts it references. Instead, its primary concern is to unmoor signifiers from their histories and use them in a mix of disjunctive styles that reflects postmodernity’s preoccupation with freeing up signifiers of history from the demand that they yield the truth of their pasts⁷. This is, for example, what’s at the core of Rowing Blazers’ dialectic. Named after a sport that is decidedly white, upper-class dominated, Rowing Blazers does not shy away from its connections to the elite world. Nevertheless, through pastiche and a conscious effort to diversify model representation in their Ad campaigns, the brand seems to attempt the decolonisation of Ivy clothing. The collaboration with lovable elephant cartoon character Babar — whose story according to some is an implicit endorsement of the civilising effects of French colonialism — shows indeed how, through irony and irreverence, the underlying narrative of Rowing Blazers’ strategy negate any colonialist reading of Babar.

As soon as the “Ivy Style” began to feel like a costume, preppies ditched the suit-and-tie uniform and adapted to the current youth-led streetwear moment. With bright colours and sporty fabrics blending with skate and punk influences, all the existing stylistic codes collapsed. A$AP Rocky sporting the Gucci horsebit loafer — once indissolubility tied to the realm of the 80s finance culture — not only demystifies the loafer but, through appropriation and reinterpretation, it transcodes a cultural object reusing it in an affirming and empowering way.

With Miles Davis becoming a regular customer at the Andover Shop, the “Ivy Cool” wave started gaining popularity and Charlie Davidson (the Andover Shop proprietor) became a bridge figure between Modern Jazz and the Ivy. Similarly, the new politically-activated post-preppy brands (Noah, Awake, RB, just to name a few) — through pastiche and remix — is bridging two worlds: namely the one of blue-blooded private University goers and the one of street kids wearing tiny beanies and flipping decks around the city. Taken out of their original context, prep’s crests, mater-branded sweatshirts and hats become evocative of merch whose stuffiness is transformed into fashion’s more benign version of elitism: exclusivity⁸ — resulting in a Baudrillardian short-circuited system of signs.

Baudrillard argued that consumer goods moved from their utilitarian dimension to a symbolic one. With symbolism, clothes — originally appreciated and enjoyed as a function of their practical value (use value) — are evaluated for their symbolic or emotional meaning (exchange value). In this sense, wearing a hat emblazoned with the logo of an American private school is not so different from hanging a Supreme deck in your apartment even though you can’t skate: they both signify exclusivity. But, according to Baudrillard, such signaling is purely self-referential and bears no relation with any existing reality. Take, for example, the way in which fashion design can empty religious symbols (e.g. the cross), ethnic symbols or national symbols, by reducing them to their mere aesthetic quality.

The idea that the moment clothes make their way out of factories, those are subjected to people’s interpretation and appropriation that, stripping down their utilitarian value, turn them into cultural signs, is not new. Barthes extensively wrote about fashion codes and its grammar, often using the raincoat as an example: it protects against rain, but also and irremediably, it points to its status as a raincoat. What’s new though is the way fashion objects gain their cultural value.

The Handover Shop proprietor once noticed that “People made things a classic, not manufacturers.” But times are different and nowadays the discourse around fashion is no longer articulated exclusively by shops. Social media, clubs and art galleries (just to name a few) are part of the discourse too. You can buy a pair of Nike Jordan 1 either in a store (both online and offline), on a reselling platform or even at Christie’s. Articulating a Foucauldian discourse around what is “fashionable”, these institutions make certain “styles” and “values” present while others are made absent. In such a way, they guide the production of cultural meaning even before the objects of fashion physically meet the society.

In such a scenario, the post-preppy aesthetic is a strategy of superficial appearances involving the charms of games and artifice that negates the seriousness of reality, meaning, morality and truth. As the objects of fashion were completely detached from their use value, the heroes of production, such as the factory workers, entrepreneurs, pioneers and explorers, were replaced by idols of consumption, such as movie stars, sports personalities, bloggers and celebrities⁹. Transitioning from a purely referential function that encodes symbolic meaning to a purely self-referential function that marks the end of meaning, post-modernity caused the rules of fashion to collapse in a more disordered and non-systematic combination of clothes, styles, looks, subcultures and classes, eventually condemning every attempt to create a new style into a form of eclectic fashion pastiche. In this sense, the post-preppy aesthetic aims for ‘theatrical sociality’ (to quote Baudrillard) which ‘delights in itself’ in aesthetic pleasure, eventually turning its aesthetic features into signs without a message.

  1. Chensvold, Christian. 2020. “Miles Ago.” Ivy Style.
  2. Davis, M., and Q. Troupe. 1989. Miles, The Autobiography. New York: Simon & Schuster.
  3. Barthes, R. 2006. The Language of Fashion. Edited by M. Carter. Oxford: Berg. (p.142)
  4. Trubetskoy, Nikolai S. 1969. Principles of Phonology. Berkeley: University of California Press.
  5. Dyer, R. 2007. Pastiche. New York: Routledge.
  6. Sturken, M., & Cartwright, L. (2018). Practices of Looking (3rd ed.). Oxford University Press.
  7. Ibid.
  8. Samuel, Hine. 2018. “Rowing Blazers Is Proving That the Prep Revival Is Just Getting Started”. GQ.
  9. Rocamora, A. 2015. Thinking Through Fashion: A Guide to Key Theorists. London: I. B. Tauris & Company.

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Collective Identities is a counter-academic research project by Bocconi Business&Arts in conversation with underground fashion distributor and cultural hub Slam Jam, investigating Youth, Institutionalism and Fashion.



Francesco Daprile

Graphic designer interested in Media Studies, Modern Philosophy, Music and Fashion. Bocconi & UAL — London College of Communication alumnus.