From across the street, William Yan spots a woman in a houndstooth skirt and fur coat; she wears a wide-brimmed hat and stands no less than 5 feet 10 inches tall in Mary Jane heels. As Yan undecidedly fingers his camera lens, she has already begun to strike a demure pose, tilting her head back in a way best described as calculated, the brim of her hat casting a shadow on her comma of a smile. She knows he wants to snap her. She spotted Yan’s camera from across the street. She is a professional.

William Yan at "the office."
Yan is a New York-based street style photographer who got his start in a Photography 101 class right out of high school. He photographs New Yorkers whose style “has a presence,” and today, I am following him around on his mission to shoot new subjects for his eponymous blog, WilliamYan.com.
As we make our way down the remaining SoHo blocks, passing at least three other street style photographers whose eyes peruse the touristy SoHo crowd for sartorial diamonds in the rough, Yan’s term for this area of Manhattan, “the office,” seems surprisingly accurate.

"Sometimes you have to dress the part and play the role," Yan says of the woman he photographed.
“I have to find different streets to walk on so I don’t run into the same people all the time,” says Yan after he exchanges business cards with the woman, who also happens to be the street style photographer behind NYCStreetfile.com.
“So we just saw her, and now we just passed by a male one,” he says, glancing over his shoulder at a man holding a camera on the corner of Greene and Spring streets. “I’d rather catch someone who’s a little odd, who didn’t dress for the camera.”
Street style photography has become almost unavoidable for those with even a minor interest in fashion: hundreds of blogs dedicate their posts to street style photos, fashion week attendees’ ensembles are documented piece-by-piece by photographers like Tommy Ton (who has an exclusive contract with Condé Nast’s Style.com), and style icons have emerged who capitalize on their internet presence by turning internet fame into personal brands and successful careers (see: Nick Wooster).
Street style photography, however, is not a new concept; if anything, the term alone has become more popular than the form itself. Yan started blogging his photographs in 2008; he could be considered one of the early adopters in today’s crop of street photographers who’ve emerged in recent years, but he readily gives credit to his predecessors. Bill Cunningham, for example, the New York Times street fashion photographer, has shot candids of New York’s quirkiest and most well-heeled men and women for over 50 years. And in a recent documentary about the elusive veteran photographer, Vogue editor-in-chief Anna Wintour famously says “we all get dressed for Bill. And it’s one snap, two snaps or he ignores you, which is death.”
This concept of getting dressed for the photographer, however, does not end with Anna Wintour, or even with fashion insiders draped in designer pieces.
“I’ve heard stories of people recognizing someone while they’re on the street working, and going out of their way to keep crossing their path, hoping to get snapped,” says Jian DeLeon, a staff writer for the Style section at Complex Magazine, a men’s collector’s guide.
Because street style has been editorialized in clothing brands’ lookbooks and fashion magazines, more people recognize its style, an unusual and sometimes confusing mixture of subjects who are both posed and shot candidly; these subjects usually look effortless and comfortable, but the lighting is often just so, and the framing seems meticulously planned. Yan’s photos, however, are slightly different than many other blogs; for one, most of his photos are not posed.
“I think his greatest strength is his eye; he’s not out there shooting what everyone else is,” says Sean Hotchkiss, a contributor to GQ who writes for the magazine’s blog, The GQ Eye.
Most of the photos that appear on Yan’s site achieve that nonchalant look, though he says he poses certain photos, which almost come off as portraits. The men and women on his site usually look as if they’re on their way to meet a friend: they’re never over dressed, have little makeup on, and often aren’t even looking at the camera.

Two subjects on William Yan's blog

Her Hermés Birkin bag caught Yan's eye
Though I only get a short day to witness Yan’s “eye” at work, I notice there are photos in his camera of famous faces he has yet to put on his site. A photo of the eccentric fashion icon Daphne Guinness, for example, stays stored on his memory card, yet to see the light of the blogosphere. Many would use her name to gain site visits and quick hits, but he shot her in passing, he says, and isn’t satisfied with the end result. He’s picky about what he puts online, because for a street style photographer in today’s click-happy culture, his site serves as a sort of a business card/portfolio hybrid.

Supermodel Karlie Kloss, shot backstage at Oscar de la Renta's runway show during New York Fashion Week.
This past year, he earned paid work shooting backstage photos for Oscar de la Renta during New York Fashion Week, but he hopes to expand his success to a global level, a goal other street style photographers share.
“That’s really the whole point of this; you want to explore different cities and find inspiration, all while making a living,” says James Jean, one of the photographers behind popular women’s fashion street style site Citizen Couture. Jean has already shot in Paris, New York and Milan, but wants to explore other fashionable cities like Stockholm.
Like any creative industry with lots of eligible players, the competition is relentless, and success becomes less definable. At some point, these men and women have to pay their bills.
“It’s become so popular that it’s not as fun maybe, as it used to be. But I have to keep shooting, because that’s just what I do,” Yan says, barely finishing his sentence before he halts abruptly, snapping a woman in purple who seems to have popped out of nowhere. He looks at the image on his LCD screen, shrugs, and rests his camera on his hip again. He doesn’t seem bothered by the down time, or the blocks and blocks of walking up and down New York’s uneven downtown streets.
“In a way, it’s like I’m a hunter,” Yan says. “I’m hunting for style.”

William Yan searches Broome Street for subjects.