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Take a moment to think about clothing — items, looks, brands — that are recognisably, classically American: the basic vocabulary that is used and reused in the construction of American style. A surprising amount of what leaps to mind for me, and I think for a lot of other people, fits into one of two broad categories.
The first category starts with the most important pieces of American vernacular of all — blue jeans and T-shirts — and extends to everything from Timberland and Red Wing boots, Carhartt canvas jackets, Woolrich plaid mackinaws, chore jackets in all their permutations. Western wear, from snap-button shirts to cowboy boots to silver-and-turquoise jewellery, all fits in here. We could call all this workwear, just to have a name for the genus.
The other includes Brooks Brothers button-collar oxford cloth shirts; J Press tweed jackets; Bass Weejuns and penny loafers generally; Docksides and Sperry boat shoes; odd lightweight cloths such as madras and seersucker; LL Bean duck boots and field coats; khaki trousers; cloth belts with brass buckles; aviator sunglasses; and so on. We can call this preppy clothing, though pedants like me will prefer the term “ivy” for much of it.
This dichotomy is not comprehensive. First of all, I’m thinking of it mostly in terms of menswear. Readers who know something about women’s clothes will see things differently. And there is plenty of sartorial Americana that falls outside of this taxonomy. For example, the basketball sneaker, from the Converse All Star to Nike collectibles. What is now called “streetwear” draws on and transforms both styles. Still, a surprising amount of truly American style does fit into one branch or the other.
If, like me, you think of clothing in terms of cultural capital as much as its visual properties, you will notice that the dichotomy maps very well on to Americans’ jittery and contradictory attitudes towards its class system. The preppy branch speaks to a fantasy about moneyed ease, about how the upper classes, free from aspiration, fritter their time away sailing, hunting, playing tennis. It is east coast and old money. The workwear branch, on the other hand, speaks to a fantasy of earthy authenticity, of autonomous, honest work. It is western and owes nothing to inheritance and pedigree.
The appeal of both fantasies is apparent and both are peculiarly American, opposed though they may be. We all aspire to be educated and successful, and to be totally relaxed and sophisticated about our success. We all want to be the Kennedys at Hyannis Port. At the same time, we hate all that. We want to be rugged individualists who trust in our hands and live by our word, who don’t want the rich man’s dollar, his country club or his company. To be American is to entertain both the urge to separate from the working class and to identify deeply with it.

The person who recognised, over half a century ago, that these two American identities were both fundamental and closely intertwined, was Ralph Lauren (a working-class kid from the Bronx who aspired to better things). That recognition — and his eye for how the two styles played off one another, along with his entrepreneurial genius — made Lauren the single most important person in American style over the past 50 years. His brand continues to operate in both modes. On the western side, for a Polo Ralph Lauren collection released last year, the designer partnered with Diné (Navajo) textile artist Naiomi Glasses. Back east, the Purple Label fall 2024 collection still features a model in khakis and loafers, with a pink cable-knit sweater hung jauntily around the shoulders.
The similarities between the two Americanisms are as interesting as the differences. Both the preppy and the workwear traditions are essentially about the outdoors: the idea of physical freedom and vigour. So is the idea of casualness. Part of both codes is not looking like you are trying too hard.
The denial of the class system in America is coeval with the class system itself. We Americans all acknowledge that there are wide disparities in wealth. What each of us denies about ourselves is that class retains a powerful moral, social and aesthetic valence. The thinness of our denials is revealed by the incredible persistence of the two styles. Even as it has become standard to criticise the elite and their institutions, prep marches on. And even as we have become a nation of service workers and data manipulators, workwear is everywhere. Class consciousness is inscribed in our clothes.
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