Though "street style" as a term — and blogger-making, bill-paying phenomenon — came into consciousness in the age of the Internet, the concept (surprise!) has been around for as long as people have been, well, wearing clothes and walking on streets. Today's big names certainly owe a lot to the likes of Bill Cunningham and his unexpected shots of fancy people going about their daily business, first published in The New York Times in 1978. But, a more ambitious history could trace the line of influence all the way back from Charles Baudelaire's written observations of dandies in The Painter of Modern Life to contemporary sites like The Sartorialist.
Since so much of fashion (and fashion photography) is cyclical, we thought we'd take a look back at the OG images that capture real-life style stars showing off familiar trends, way before they came around again. The result of our deep, archival dive is a collection of images dating back to the '20s that have serious sartorial staying power — no over-shuttered street style stars involved.