Bill Cunningham’s Street Style April 19 2022

I’ve always thought that photography is the perfect way to capture a moment as perfectly as it can be. When I was a senior in college, I forced myself to stay up until the designated 2am window when I could begin to register for classes to ensure I got myself one of the 12 spots available in the high-demand photography class.  After half an hour of just trying to get the website to load (anyone who’s had to go through this process during college can relate to this, unless you were the type to choose sleep over registering for classes and took your chances on what was available in the morning), I finally finally finally secured my spot.

I was a little taken aback on my first weeks of the class when the professor expected us to Photoshop our photographs before submitting them. Where was the authenticity in that?  I liked photographs because they were real—if they showed someone with a pimple or an errant piece of hair, who cares?  Nothing more real than being imperfect.  I had long admired the photographs of Ansel Adams and Dorothea Lange, and they certainly did not have Photoshop to improve upon their images.

Bill Cunningham at a Mercedes-Benz fashion show. Image courtesy of

I think all of this is why I’m drawn most to candid pictures—because in a world where everything is touched up, candids are as real as ever. It’s real emotion, real expressions, real fashion.  Until very recently, for decades and decades, no one did candids like Bill Cunningham and his “On the Street” column for The New York Times.  He was the king of Street Style.

Bill Cunningham photographing Carolyn Murphy for Harper’s Bazaar. Image courtesy of

Like many photographers, Cunningham didn’t start out behind the camera. Born in Boson in March of 1929, William John Cunningham, Jr. was the second of four children.  He showed an early interest in fashion—millinery, in particular.  During his teen years he worked at Bonwit Teller, but when it came time to go to college he accepted a scholarship to Harvard.  That proved to be short-lived, however, and Cunningham dropped out after only a few months.  From there he moved to New York City where he started working for his uncle’s advertising agency.  His interest in fashion had never died though, and soon he left that position and opened his own millinery shop.

Bill Cunningham in 1967 with his first camera.

In 1967 Cunningham got his first camera, and began taking pictures on the street. Once he realized fashions were changing and the era of hats was quickly coming to an end, Cunningham decided to pursue photography full time and soon became a staple figure on the streets of New York, snapping pictures of real people wearing real clothes in their real, everyday life with his bicycle in tow.

Pretty in pink, “On the Street” edition. Image courtesy of

Cunningham created montages of his photographs for his “On the Street” feature in The New York Times—themes of stripes, shades of blue and cream, shoes and leather, jackets and rolled pants.  He attended all the social events in the city, preferring to go in the role of photographer and not as guest.  Through his photography, he created what can essentially be viewed as a visual record of fashion through the ages.

Photographing in the rain. Image of

Cunningham became an icon in New York, even being named a living landmark by the New York Landmarks Conservancy in 2009 (if anything ever screamed “You made it!” I think this does). The city became his canvas, and his focus on what was taking place in the fashion scene from a street level made him famous.

One June 25, Cunningham died in Manhattan at the age of 87 after being hospitalized after suffering from a stroke. Although his bicycle will no longer be seen along the streets of New York (it is said that he had over 30 bicycles throughout the years, replacing them as they were stolen or became too worn to use), his work has made a lasting impact.  Rest easy, Mr. Cunningham.


Written by Heather Cox for Rice and Beans Vintage.