Editing the Late, Great Bill Cunningham

Editor Christopher Richards reflects on Bill Cunningham's memoir, Fashion Climbing, and the icon's milliner days.

Bill Cunningham

There’s a quality to Bill Cunningham’s photo archive that can only be described as sacred. This has little to do with its appearance—it’s merely a few dozen identical metal filing cabinets and a handful of common packing boxes. But the reality of what these files and boxes contain is profound.

Bill arguably kept the most complete record of the people of New York City in the last half-century. His files were encyclopedic and meticulously maintained: one drawer might contain photos of an East Village party in the late ’60s with a handwritten note on precisely what Andy Warhol wore that night; another may hold fur-laden women he had seen going to the opera on a December night, his descriptions punctuated with exclamation points to express his joy at how a particular group were like birds of paradise.

He preserved thousands and thousands of images, a loving archive of you and me and everyone we know and don’t yet know. If there’s a photo gallery in heaven, depicting us in our most fabulous moments, I’m certain that Bill Cunningham is its chief photographer.

Image Credit: Anthony Mack

In my role as editor of his memoir Fashion Climbing, I made two visits to Bill’s archive to search for photographs to punctuate his story. The book depicts his early days in New York, before he became the iconic street-style photographer for the Times. In Fashion Climbing, we learn how Bill came to New York as a teenager obsessed with fashion and devoted, almost religiously, to beauty. As a young adult, he became a hat designer and earned a reputation as one of the most outlandish and beloved American milliners of that era. As Bill puts it, “The principal reason for me to start my own business was to bring happiness to the world by making women an inspiration to themselves and everyone who saw them.”

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When I first read Bill’s memoir on submission, I didn’t realize how shocking his creations as a designer were. It’s a cliché, but please believe me when I write that there are some images words simply cannot capture. Fashion Climbing details his designs: “a helmet of gold lamé, with big black feathers shooting out of it,” “a giant head-covering clam,” “a huge umbrella-size straw brim with long celluloid fringe sewn around the brim edge, hanging to the floor,” and—my personal favorite—a hat “with a glamourous face of felt . . . that had a real cigarette glued onto the lips, a long crystal drop earring, and a mop of pink feathers for hair.”

Image Credit: Bill Cunningham

Descriptions like these are peppered throughout the clean typescript he left behind for his book, only discovered after his death in 2016. Many people don’t know what a creative genius Bill was during his millinery days, and I wanted readers to have a taste of that, so I was on the hunt among these cabinets and boxes for photographs that would illustrate his brilliance and the bohemian world he existed in.

Bill only became a photographer in earnest after he closed up his design business—sales were dwindling as hats went out of fashion—so most of the images in Fashion Climbing were drawn from two well-worn scrapbooks in which Bill memorialized his days as a designer. The scrapbooks have the look of a secret diary, and they were kept separate from the rest of his photographs. They held fashion magazine spreads, reviews of his runway shows from the likes of Vogue and The New Yorker, and, of course, photographs of one outrageous hat after another.

While the images I gathered are from the decades before Bill’s columns ran in the New York Times, there’s a clear connection between Bill’s work in the ’50s and ’60s and the legend he became. There’s so much uninhibited joy and creativity in the pages of his memoir. Bill was constantly driving himself to be more original, more exuberant, to let go of his fear and shame to create something truly bold and new. And this is what the photographs for his column On the Street so often celebrated, whether it was the pastel dandies of the annual Easter Parade, his signature women leaping over puddles in stilettos, or the maximalist personal armor of his muses like Iris Apfel and Editta Sherman.

Toward the end of the memoir, I’ve included a few of his early shots that gesture to the future—Diana Vreeland in all her glory, a young man in a homemade kilt at an East Village party, a model strutting down the runway for Yves Saint Laurent—as Bill began to develop his eye as a photographer.

Image Credit: Bill Cunningham

Bill could make himself invisible, and he was known for his monkish devotion to his work. Existing in the world of fashion, a demimonde so often characterized by wealth and excess, Bill spent much of his life sleeping on packing crates between these file cabinets in his rent-controlled apartment above Carnegie Hall, complete with eccentric neighbors and a shared bathroom down the hall. Some writers have seen a strain of self-abnegation and austerity in the way Bill lived his life. But Bill had exactly what he wanted; as he writes, “when I would feel the pangs of hunger, I would go out looking in store windows and feed myself on beautiful things.”

It’s no coincidence that his perch as a street photographer was the corner of Fifth Avenue and 57th street, standing aside the exquisite displays of Bergdorf’s, looking for the swirl of a flamboyant skirt or a brightly dressed man peacocking up toward Central Park.


Featured Image: Ramin Talaie/Corbis via Getty Images; Bill Cunningham Author Photo: Paul Stein

Iconic New York Times photographer BILL CUNNINGHAM was the creative force behind the columns On the Street and Evening Hours. Cunningham dropped out of Harvard and moved to New York City at 19, eventually starting his own hat design business under the name “William J.” His designs were featured in Vogue, The New Yorker, Harper’s Bazaar, and Jet. While covering fashion for publications including Women’s Wear Daily and The Chicago Tribune, he took up photography, which led to him becoming a regular contributor to the Times in the late 70s. Cunningham was the subject of the documentary “Bill Cunningham, New York.” His contributions to New York City were recognized in 2009 when he was designated a “living landmark.”

About Christopher Richards

Christopher Richards

CHRISTOPHER RICHARDS is an Editor at Penguin Press. He began his career at Farrar, Straus and Giroux, and he has written for The New Yorker’s “Page-Turner,” The Paris Review Daily, 4Columns, and The Nation.

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