My favourite famous preppies

Preppy – or Ivy League – is one of the core foundations of casual culture, even if your average terrace type wouldn't know his J Press from his J Crew, or a full term at Princeton from a weekend away in Martha's Vineyard. 

No matter, through osmosis, and prep's influence on Italian, French and Spanish luxury sportswear, Ivy style still pretty much defines what smart – and I mean, sharp – casual is about. 

Preppy grew out from an American take on traditional Savile Row tailoring, and reached its pinnacle in the late ’50s and early ’60s, when it absolutely defined the ideal of the clean-cut American male. 

From late-night Hollywood bars to the jazz clubs of Manhattan, the Ivy League uniform of button-down shirts, natural-shouldered jackets and penny-loafers was the go-to style for film stars, politicians and musicians alike. Dustin Hoffman, Paul Newman, Steve McQueen and Jack Lemmon – they all wore it, and they'd never look better.

Here then, a pick of my favourite famous preppies in the years before America lost its innocence, when no one had heard of Vietnam or Agent Orange or dress-down Fridays. An America you really could believe in.

Keep it sharp, gents.


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