If Bill Cunningham is familiar to you, it’s most likely for his work in his second career as a photographer. While his fashion photos and written columns made him famous, he originally entered the fashion world as a milliner.
Growing up in a Boston Irish Catholic family, he said he paid more attention to women’s hats in church than services. His career in fashion began as a stock boy at Bonwit Teller. After a two month stint at Harvard, he ditched college and moved to New York, where he again got a job with Bonwit Teller. Still fascinated by hats and fashion, he had dabbled in creating fanciful hats since his teen years.
Drafted into the Army during the Korean War, he was stationed in France, exposing him to European high fashions of the day. Once back in New York he continued creating hats in earnest. Soon he had a following of fashionable and wealthy women. Encouraged to write about fashion as well as create it he began writing freelance for Women’s Wear Daily for extra income.. He also wrote about fashion for the Chicago Tribune.
While still making hats, he saw the shift in fashion coming in the 1960s and soon took up street photography. A self taught photographer, he was fascinated by the outfits seen on the streets of New York City. His millinery closed in 1962. His career officially shifted to photography and writing about fashion. Bill’s favorite place to photograph was the corner of Fifth Ave. and 57th street. 
Bill Cunningham was well known for his philosophy of not accepting gifts for his work. He felt money was corruptive and that liberty to do as he pleased was worth far more. He lived a spartan lifestyle, inhabiting one of the very smallest apartments inside of Carnegie Hall for many years. The apartment had no kitchen or bathroom and was furnished with rows of file cabinets filled with photos. Known for his blue workers jacket and black sneakers, he could be seen on his bicycle riding the streets of New York City with his camera. Bill photographed fashion that he found interesting and imaginative. His focus was not on the wearer, but on how the outfits were worn. He once took a photo of Greta Garbo because he was so taken with her coat he failed to recognize her.
He set out with his neighbor in Carnegie Hall, Editta Sherman known as the Duchess of Carnegie Hall, to document a collection of vintage clothing alongside buildings throughout New York of similar age as the outfits. The final product became a book featuring a small portion of the 1800 photos and 500 outfits they had amassed over several years. The book, Facades, was published in 1978.
The number of celebrities photographed by Bill Cunningham could fill multiple volumes. He was invited to photograph every important event in New York. Rather than the typical celebrity posed photos, he preferred to take shots when folks were unsuspecting, natural poses, people hurrying to work, or deep in conversation and uninhibited. It was those who created their own style that caught his eye rather than the created and posed fashion icons shown in the magazine spreads. His columns for the New York Times ran from February 1989 until shortly before his death in 2016. He received innumerable awards throughout the years and several books and documentaries have been written and made about him over the years.
To learn more start here: Bill Cunningham Wikipedia
To watch the Documentary follow this link: Bill Cunningham:New York
To see some of the hats at auction made by Bill Cunningham start here.
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