Rihanna, Bill Cunningham and Stella McCartney at a fashion gala in the Metropolitan Museum of Art in New York City, 2014

In 2016, legendary New York street photographer Bill Cunningham died, aged 87. The fashion industry, and everyone who was lucky enough to be photographed by him, collectively remembered how he captured the best fashion show there ever was: the one on the street.

Cunningham began taking photos in the 1960s, after shutting up shop as a milliner and a brief stint in the army. Rising to prominence in the 80s with his On the Street column for the New York Times, it is clear just how expertly Cunningham sees pavement and pedestrian crossings as a catwalk of their own.

The 2010 documentary Bill Cunningham New York reveals the man behind the camera. Filmed in his 80th year, the documentary follows him around on his bicycle – easy to spot in his signature blue worker’s jacket – as he darts between yellow taxis, nimble and quick, and ready to do anything for the shot.

Cunningham’s no-fuss personality played a huge role in his ability to spot the best leopard print, or the coat with the nicest collar. He was famously not interested in the status of stars, and mentions early clients in his hat shop – Ginger Rogers, Joan Crawford and Marilyn Monroe – offhandedly. While attuned to the who’s who at society events, he is described as a true egalitarian: for him, it was only about the clothes.

Of his many high-profile subjects that are interviewed in the documentary – including former magazine editors Iris Apfel (always eccentrically dressed, even now at 102) and Annette De La Renta – it is Anna Wintour who says it best: “We all get dressed for Bill.”

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When he was not on the street, he was in a cubicle in the New York Times offices, where we see the painstaking process of composing Cunningham’s pages. Perhaps this week is all about graphic print T-shirts or “shoes and legs”, but Cunningham’s eye demands the layout be perfect and best serve the reader. For them, he is identifying trends (after all, he saw them first) – the denim dresses and leggings of the 80s, the fanny packs and baggy pants of the 90s.

While he often photographed extravagance, Cunningham’s life was simple and private. His flat is crammed with fashion books and filing cabinets full of negatives of every photo he has ever taken. His clothes hangers hang off cabinet handles; his bed is on slats in between shelves. He has never owned a television, and has no kitchen.

Rihanna, Bill Cunningham and Stella McCartney at a fashion gala in the Metropolitan Museum of Art in New York City, 2014. Photograph: BFA/REX/Shutterstock

By the time the documentary is being filmed, Cunningham is hard of hearing, but his joy lays in what he sees. His energy is infectious: it is more than enough to make you never look down when you’re walking again, in case you miss a fashionable passer-by.

Dispersed throughout are stories from those Cunningham photographed most, like one man who made his pants from the fabric of an old ottoman, and the matching suit jacket out of a sofa. There are also pivotal moments from the fashion world: sitting in the front row of shows at fashion week in Paris – a city that he says “educates the eye” – Cunningham takes photos with rapturous energy even though he is old enough to remember Yves Saint Laurent’s first ready-to-wear show in the 60s, where he was also taking photos. How times changed.

Bill Cunningham New York is about fashion, but it is also about a man’s devotion to his self-taught craft. What would New York have done without Bill Cunningham? He showed the city that on every street corner there can be something to see. In his own words: he who seeks beauty will find it.

  • Bill Cunningham New York is streaming on Prime Video and Apple TV+. For more recommendations of what to stream in Australia, click here

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