On The Fashion World’s Love Affair With Street Style

Two summers ago, something important happened. Something big. Something that filled me with such joy and personal satisfaction that I still catch myself daydreaming about it. Two summers ago, I was photographed by Bill Cunningham. BILL CUNNINGHAM. The man, the myth, the legend. The New York Times fashion photographer whose “On the Street” column makes the Sunday Styles a must-read. That Bill Cunningham.

Bill is the original street style photographer. He began shooting way before blog was even a word. Bill’s so old school that he still uses film. Bill is, in a word, major. Every morning when I get dressed, I wonder if my outfit would be Bill-approved. And I am certainly not the only one. Maybe I’m going out on a limb here, but I think it’s safe to say that every style-conscious urbanite fantasizes about being photographed on the street in their most effortlessly fabulous outfit.

Long gone are the days when Bill and the Times were the only game in town. Now we have Scott Schuman, whose photographs on The Sartorialist make everyone look like a model. His girlfriend Garance Doré provides a Parisian perspective over at her eponymous site. Tommy Ton does his thing at Jak & Jil, while Yvan Rodic holds it down at Face Hunter. And the list goes on.

This all begs the question: why do we care? We care because as much as we dress for ourselves, we hope someone (anyone!) will notice. And when that someone has a career predicated on taste, their noticing carries a certain weight. Call it silly, call it superficial, call it whatever you want — but for the fashion obsessed, there is no greater compliment than a photo request from a style photographer. It’s not at all about fame or recognition, as the photos themselves end up being pretty anonymous in published form. It’s about feeling appreciated, sartorially.

Bill and I began a courting ritual of sorts some time during the first few days of June 2008. I was interning at Yves Saint Laurent, conveniently located at 57th and 5th, one of Bill’s favorite spots to shoot. He stations himself on that decadent corner (Bergdorf, Tiffany and Louis Vuitton all call it home) most weekday mornings, which makes sense given the high volume of fashion house bigwigs making their way to work in the area. I was no bigwig. Rather, I was a lowly (but well-treated) intern for the visual team, where black skinny jeans were my standard uniform.

We saw each other at least once a week. I would smile, he would nod. I started to strategize. To catch the eye of a street style photog, you must stand out, but not too much. Quirky chic is good, over-the-top is bad. While one can pretty much guess what kind of outfit Scott will like, Bill works with themes, making it hard to know just what he’s looking for. One time I tried to bait him with an obnoxiously loud pair of bright orange Marni jellies. He didn’t bite. He merely nodded. After weeks of similarly fruitless efforts, I was sad Bill didn’t deem me Style section-appropriate, though I still relished our non-verbal exchanges on that busy corner.

The week before I left New York to head home before starting my junior year of college, I made one final trip to our spot. I was dressed head-to-toe in black (including black gladiators, because 2008 was the summer of the gladiator), accessorizing with big glasses, an armful of bracelets and a bright red bag that had been my YSL purchase of the summer. I saw Bill. He saw me. I smiled. He nodded. As I crossed the street, he took my picture. I beamed for the rest of the day (hell, I beamed for the rest of the week).

That Sunday, as I sat at home on my couch in St. Louis, I went on the Times website as I do every Sunday morning to check out the “On the Street” slideshow. The title was “Ravenwood” and the theme was black — lots of black. My stomach flipped. I was wearing black — lots of black — when I saw Bill earlier that week. Sure enough, there I was, with 48 seconds left in the slideshow. I stared at the screen in disbelief. I was certain that yes, this was undoubtedly the best thing that ever happened to me.

Bill had accepted me into the fold. He thought I was worthy of his column, the column I read so faithfully every week. I was touched. I was honored. And in the end, yes, I felt appreciated.

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