Our 2,821 Favorite Street Style Photos Ever

Refinery29 started featuring street style shots shortly after our launch in 2005. In 2009, we began cataloguing the outfits at fashion week, and in 2014, we even released a book, Style Stalking, dedicated to personal style. Today, street style has become a multi-million dollar business. But before your Insta feeds get saturated with people in the latest Raf Simons bag and Virgil Abloh Nikes, we're taking a look back at the history of modern street style and revisiting how R29 has been covering the phenomenon since the beginning.

Are there any two words as polarizing in the industry as 'fashion blog?' Probably not. A little over a decade ago, self-proclaimed style aficionados around the world took their love of fashion online, opening Blogspot accounts, launching websites, and thinking this will be a good hobby. It was the birth of the modern day #OOTD, the idea that getting dressed could mean getting seen, and a concept that would unleash a pandora’s box of bloggers, photographers, and bloggers-cum-photographers onto, well, the streets.

In 2005, taking pictures of what “regular” people were wearing as they went about their “regular” business wasn’t new; Bill Cunningham at The New York Times, FRUiTS magazine in Japan, and a variety of fine-art photographers, from Henri Cartier-Bresson to Helen Levitt and Amy Arbus, had been documenting the streets, in the United States and in Europe, since the early 20th century. But what this mid-aughts crop of photographers — people like Scott Schuman, Tommy Ton, Phil Oh, and Yvan Rodic — did was turn the lens onto people who, until very recently, lived their lives behind the camera.

It’s hard to believe that there was a time when stylists and editors were anonymous. The standard person didn’t know such a job existed, or what it entailed; if you were a fashion obsessive, you may have recognized certain names — Melanie Ward, perhaps Camilla Nickerson — but it would’ve taken a lot of sleuthing to figure out what they looked like (especially in the pre-internet age). But street style was the perfect symbiotic relationship between fans and editors, an exercise that everyone, whether they were interested in fashion or not, could get involved in. For fashion fans, it was a chance to see how their favorite creators dressed, and how those shoes that had just walked down the runway would look like “in real life.” For those who thought fashion was “silly,” it was a chance to look at just how outrageous its participants dressed.

Season after season, the street style juggernaut grew. Suddenly, editors found themselves the center of the story; women like Anna Dello Russo, editor-at-large at Vogue Japan, and Giovanna Battaglia Engelbert, then-fashion editor at L’Uomo Vogue, women whose style was impeccable and, at least back then, attainable, became household names. While some editors continued to live their lives as they did before the photographers invaded, others took advantage of the situation. changing outfits between shows and wearing full looks of whatever designer’s show they were attending (weirdly enough, this has never been seen as a faux-pas, even though it is not unlike wearing a band’s shirt when you go see them in concert). The outside of a show venue became as much a show as what was happening inside.

As the editors’ stars grew, a formula developed — Do you have access to the latest fashions? Are you able to walk across cobblestones while wearing vertiginous shoes? Can you travel to fashion weeks in New York, London, Milan, and Paris? For those able to answer yes to all of the above, a new career — “street style star” — was born. These mostly young women would parade up and down the sidewalk, the avenue, the Tuileries in their freshest outfits, preening and “peacocking” for the cameras — whether they ever set foot inside the venue and witnessed the fashion show was beside the point. Eventually, they too would become household names, be re-christened as #influencers, sit front row at the shows, and go on to make an extremely comfortable living out of posting pictures of themselves wearing the latest designer clothes on their blogs and, later on, their Instagram accounts. Some would even become fashion editors themselves.

While authenticity was the driving force behind the early success — and interest — of the street style phenomenon, it didn’t take long for things to change. As soon as people started dressing up for the sole purpose of getting photographed, the vibe was different. After all, is it really #inspirational to see a woman in a sheer dress, exposed breasts and all, during a blizzard? The backlash was inevitable, really.

In 2013, four years after Dolce & Gabbana invited some of the street style photographers to sit front row at a fashion show — and a full four years before they would go on to cast a show exclusively with #influencers — Suzy Menkes called shenanigans on the whole thing, writing a scathing op-ed in the pages of T magazine. She wasn’t wrong entirely, but the whole thing also felt a little not with the times. After all, her iconic curved-bangs coiff wasn't an unusual sight on the pages of the very people she was criticizing. And though rumors of street style’s impending death have been greatly exaggerated — most recently by Vogue magazine editors late last year — the truth is, it’s simply the new norm.

The way we consume fashion has changed, and while nothing takes away from the pleasure of a fantasy fashion editorial shot on an impossibly beautiful woman, in an impossibly beautiful location, wearing the most expensive, exclusive clothes, and the most perfect hair and makeup — the street style photographers, and their Instagram accounts have a different raison d’etre; to bring that fantasy to earth. Now that so many designers expect their clothes to be photographed in magazines exactly the same way they sent them down the runway, the only place we have left to look for a little fashion creativity is in the streets. Same as it ever was.

February 2017

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2017 is about going all out: the brightest colors, the longest silhouettes, the largest sunglasses.

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September 2016

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Last year's golden slouchy boots are definitely good worth revisiting.

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February 2016

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Ah, this was a good season for primary colors.

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September 2015

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Coordinates ruled September 2015, whether you matched with your sister, or went for a skirt suit.

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February 2015

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All about the statement jacket.

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September 2014

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A little sheer detail goes a long way.

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February 2014

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Never forget how accessories can take your outfit next-level — a prim clutch against a puffy cape, a pink beanie, a crossbody bag that's the color of your jacket.

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September 2013

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That natural, wind-swept hair look.

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February 2012

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Long live the maxi skirt.

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September 2011

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Fit-and-flare dresses and extra-high heels. Classic 2011.

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February 2011

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Tights can really pull a look together! (Should we blame Blair Waldorf for this one?).

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September 2010

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Remember when things felt...casual?

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February 2010

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Statement glasses and animal prints are fashion classic for a reason.

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September 2009

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Way back when, no two street style looks were alike.

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