Bill Cunningham Was There For My Breakup, My Work Crises & Me

I saw Bill Cunningham nearly every weekday morning for six years. Monday through Friday, I’d round the corner from 5th Avenue onto 57th Street en route to the YSL tower and make my way past Bill's daily photo shoot outside the Louis Vuitton flagship. Rain or shine, Bill was reliably present at this early-bird post until about 8:45 a.m., smiling, chatting with the regulars (from notable editors and fashion executives to drag queens and interns) and snapping away at the outfits that impressed him each day. If I'm being truthful, I should credit him for my prompt start time at the office over those years. I was dreadfully late to pretty much anything else. But the thrill of seeing him in action, and the chance (even if it was a long shot) that he might want to photograph me was solid motivation for a young fashion addict to get up and at ‘em. Bill would be out there documenting whatever fashion moment was trending in New York at the time: fur stoles, prints on prints, skinny black jeans, wide-brimmed hats, leather pants, and leopard-print everything. If people were wearing it in droves, he was reporting on it.

Bill first took my picture when I was a lowly assistant slinging Starbucks in my combat boots, which, it should be mentioned, I wasn't allowed to wear to work yet because they weren't "on-brand." So, I would begrudgingly switch them out for my YSL Tributes at the office with the knowledge that at least someone — the one — got me.

My punctuality paid off. Bill ended up publishing dozens of photos of me in the New York Times' Sunday Styles section. He captured my yen for wearing leather jackets year-round over everything, my inability to look up from my Blackberry even when nearly running face first into other pedestrians, and got a good one of me leaving my endodontist's office, post-root canal. I’m sure I looked like a chipmunk, but I think he liked the fur I was wearing. He also got a photo of me the day I got dumped by my boyfriend and felt like total crap. It feels silly to say, but after Bill took my pic, I felt a little more confident, like myself again. That was his magic. But out of all the moments I was fortunate enough to be greeted by Bill Cunningham during my morning commute, the most meaningful was when he pulled me aside to talk shop. It was a particularly interesting time in my career; I was on the communications team at Yves Saint Laurent; Hedi Slimane, to my delight, was just named the new creative director after Stefano Pilati left, and the resounding response from the industry was largely unsupportive. It's a little strange to share this story as the world freshly mourns Slimane's departure from Saint Laurent. It might even make it tricky for many to remember how things were. But during that time, Slimane’s appointment did not receive a warm response. "Ain't Laurent" was trending so hard someone made T-shirts, Cathy Horyn had said “Mr. Slimane’s clothes lacked a new fashion spirit” in the New York Times, which went viral in the fashion world. For better or worse, the transition drummed up strong emotions in seemingly everyone. Mr. Cunningham was aware, and he had something to say to me about all of that.

One morning, he flagged me down, leaned in, and said, "They just don't get it yet, but they will. You're part of a huge moment." He knew the name change (Yves Saint Laurent to Saint Laurent) was an homage to the original ready-to-wear. He was aware that Hedi had been the protege to Yves himself — he pointed all of these facts out to me. He giggled, smiled, and added a supportive, "Hang in there. I can't wait to see more." He wasn't wrong. Much of the media who initially chronicled their distaste ultimately turned into hardcore Saint Laurent fans, many even documenting their favorite pieces with selfies on Instagram. No judgment — newness can be tricky to digest. But that little chat meant more to me than most I've had in my professional life. I'm sure he didn't know that it would be a seminal lesson in my career. Unlike many other nice conversations I’d had with industry people at the time, Bill wasn't trying to get a seat at the show (though he did get one in the front row). The man was professional, and his heart was pure. I'll never know why he decided to go out of his way to speak with me that day, but I really appreciate him doing so. A few years ago, I moved to Los Angeles and changed careers. Now, I write about fashion and work as a digital strategist. My wardrobe has certainly evolved to match the climate — not so much head-to-toe black, and the opportunities to see myself in print are a lot fewer. I’ve thought of Bill a lot over the past two days, and each time it makes me smile. His anthropological interest in what we all wore at the very least made getting ready for work more enjoyable. But much more importantly, Bill helped me find myself with the clothes I wore. I'm not sure I intentionally dressed for Bill, but I certainly felt more brave about pieces that felt out of step with my coworkers or peers because Bill liked them. His presence created a space for me where I felt I could be creative and authentic. In the stories that have come out since his death, it's become obvious that he was fashion's biggest cheerleader. He and his lens were equal opportunists when it came to personal style, and I'll be forever grateful that my style and I — during my lowest days and also my highest — had a place in his pages.