Bill Cunningham


I met Bill Cunningham during New York Fashion Week last month. When I spotted him at Lincoln Center I approached him for a photograph. He looked at me askance, like I was crazy. But he grumbled and obliged me, posing for a quick photo with his camera.

Bill Cunningham is truly the progenitor of street style with his weekly feature “On The Street” in the Sunday New York Times. He started shooting street style in the 1960s well before the internet was even invented. His corner is 5th Avenue and 57th Street, where he can usually be seen darting through traffic on his bicycle to get the shot. He is remarkably humble and lived an ascetic life in an artist studio in Carnegie Hall before being relocated a few blocks north to an apartment overlooking Central Park.

I was inspired to post my photograph of him after watching the Bill Cunningham New York documentary yesterday. Only after seeing the movie did I realize how incredible it was that I got him to pose, for me! He is notorious for shunning the spotlight and hates being photographed. And yet, he smiled! I think he was caught off guard that a young well-dressed woman was a street style photographer since all the New York ones are middle-aged men.*

Bill Cunningham New York will be playing in Chicago at the Music Box Theater, May 20 – 26.

*It’s the opposite in Chicago, we’re all female.


  1. Street Style SACRAMENTO

    The documentary hits my hometown in April and I am soooo looking forward to seeing it, he's my hero. -Bella Q
    Street Style SACRAMENTO

  2. What a great story!

  3. The Style Glossary

    Incredible! This is truly an amazing shot and he's smiling. . . love it! πŸ™‚

  4. ChiTown Fashionista

    Great photo, Amy! I can not wait to see the film.

    And I didn't realize it until you said but Chicago IS very unique in that our Street Style Photographers are all women. #girlpower

  5. WOW. a beautiful photograph of a living legend.

  6. A little presumptuous aren’t we?

    "I think he was caught off guard that a young well-dressed woman was a street style photographer since all the New York ones are middle-aged men.*"

    First off – Chicago is a midwestern city that lacks any real STYLE. Unless you consider overweight men in bad suits and sorority girls in business casual attire drinking beer to be cool. Regardless, glad to see your ego is nice and healthy. Stay in your second-tier city – New York doesn't want you.

  7. Your comment is rude. Oh, that's right, you are from New York.

  8. Wow, that's a little harsh. While I will admit that Chicago doesn't have the over-abundance of style that New York does, we do just fine. There are plenty of stylish men and women in this city. And New York has its share of "overweight men in bad suits and sorority girls in business casual attire" too, so maybe Jon should put HIS ego in check.

    And thank you, Amy, for doing what you do. Chicago is happy and proud to have you!!

  9. Clearly you don't read this blog on a regular basis "Mr. Cheese" because if you did, you would know Chicago does have style. New York isn't the only fashionable place in this country…hope that's alright with you.

    Great photo of Bill Cunningham by the way Amy! πŸ™‚

    Oh and Jon Cheese…drinking beer is cool, even in New York.

  10. Actually, truth be told, I was so underwhelmed by New York street style that I only took four people's photos the whole time I was there over Spring Break. Chicago's street style is every bit as good as New York street style during non-Fashion Week.

    A little secret from someone who's been there and seen the locations, most of the photos on the New York street style blogs uploaded year-round were taken during NYFW. The bloggers just slowly upload their archives. This gives a highly distorted view of what everyday New York street style ACTUALLY is. And it's like a cross between Wicker Park, the Loop, and the Gold Coast where all of us Chicago girls shoot.

  11. That's it! Well said.

  12. I think Jon Cheese is upset because he got rejected by some beautiful well dressed Chicagoan woman before. Poor you, got your little ego bruised. Chicago women know an arrogant douche when we see one, maybe next time bb. πŸ˜‰

  13. Anyone knows what brand is his coat? I know he wears the original French worker’s jacket with good weather, but wonder what make is this winter coat…

Leave a Reply

Comment moderation is enabled, no need to resubmit any comments posted.