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16 Iconic Street Style Moments That Capture Their Time

From Jane Birkin’s basket to Kate Moss’s muddy wellies.

Collage of Iconic Street Style Moments

If runway is a showcase of craft and artistic achievement, street style reveals fashion’s power as a tool of personal expression. From FRUiTS magazine documenting the intricate looks in Tokyo’s Harajuku District, to i-D capturing the fishnets and safety pins on London punks, to Bill Cunningham snapping shots of New York’s best-dressed, street style photography has showcased the ingenuity of those who use clothing curation as their art medium. Of course, it’s not always about the loudest outfits or those that best epitomize a specific subculture—sometimes street style is merely a display of impeccable taste. Here, we’ve gathered 16 iconic street style moments that demonstrate the enduring reciprocal relationship between fashion and culture.

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