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.
Jacqueline Kennedy Onassis
New York; circa 1970
Whether she was in first-lady formalwear or strolling down Lexington in her signature oversized sunglasses, Jackie O added an undeniable coolness to classic American prep.
Jane Birkin
London, England, April 13th, 1973
Although she is British, Jane Birkin’s effortless button-up shirts, flare jeans, bangs, and baskets made her the blueprint for what we think of as ‘French Girl Style.’
Bianca Jagger
London, England, May 4, 1979
While she is known for her showstopping Studio 54 getups, Bianca Jagger’s casual style isn’t to be overlooked.
Princess Diana
Windsor, England, May 2, 1988
No street-style list is complete without true street-style royalty.
John Kennedy Jr. and Carolyn Bessette-Kennedy
New York City, January 1, 1997
John Kennedy Jr. and Carolyn Bessette-Kennedy carried on the Kennedy legacy of impeccable American-preppy style with their own ’90s spin.
Chloe Sevigny
New York Spring/Summer 2004 Fashion Week, September 13, 2003
Chloë Sevigny has never shied away from experimental looks, but there’s something about this understated trench and sunglasses combination that radiates style icon energy.
Kate Moss
Glastonbury Festival, Pilton, England, June 24, 2005
From Woodstock to Coachella, music festivals have fostered their own distinctive style codes. If Coachella’s unofficial fashion mascot is Vanessa Hudgens’s flower crown, Kate Moss’s muddy wellies are Glastonbury’s.
Alexa Chung
Paris Fall/Winter 2009 Fashion Week, March 12, 2009
Every It-Girl worth her salt has infinitely mood board-able street style photos, and Alexa Chung is no exception.
Bryanboy and Tavi Gevinson
New York Fall/Winter 2010 Fashion Week, February 15, 2010
This image of Bryanboy and Tavi Gevinson is iconic, not only because of their outfits, but also because their presence at fashion week represents the emergence of blogs as a major form of fashion media.
Andie Arthur and Cara Delevingne
Paris Fashion Week Fall/Winter 2012 Fashion Week, March 2, 2012
Wearing boots, motorcycle jackets, and skinny jeans, Andie Arthur and Cara Delevingne encapsulate the ‘model-off-duty’ look that dominated the 2010s.
Reese Blutstein; Courtney Trop; Molly Blutstein
New York Spring/Summer 2019 Fashion Week, September 9, 2018
By 2018, the bloggers had been replaced by Instagram influencers who often coordinated their attire.
Afropunk Guest
Afropunk 2019, Brooklyn, New York, August 24, 2019
Every year, Afropunk has some of the most striking and innovative street-style moments.
Sita Abellan
Paris Fall/Winter 2018 Fashion Week, March 2, 2018
Known for her fearless personal style, DJ and jewelry designer Sita Abellan has long been a star of the international fashion week circuit.
Tamu McPherson
Milan Spring/Summer 2022 Fashion Week, September 25, 2021
Post-lockdown and months of sweatpants, ‘dopamine dressing’ with bright colors and funky silhouettes have dominated fashion week roundups.
Samuel Hine and Ella Emhoff
Paris Spring/Summer 2022 Fashion Week, October 03, 2021
GQ fashion writer Sam Hine and Ella Emhoff have established themselves as a zillennial street-style power couple.
Bella Hadid
New York City, June 27, 2022
Pioneer of the ‘weird girl aesthetic,’ whether she’s eating pizza on a stoop in briefs and Uggs or rocking funky knits and Y2k sunnies, Bella Hadid takes every opportunity to turn a look.
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