The typical street outside a fashion show could be described as many things: hectic, rowdy, eccentric, with outlandish outfits the norm. But it was rarely called gentle. Yet, listening to those inside the industry, this is the adjective used to describe Bill Cunningham, who died this week. The 87-year-old New York Times photographer captured these scenes for nearly 40 years and, to quote Lena Dunham’s Instagram tribute: “He was powerful but he was gentle and kind.” Fashion director of Tank magazine Caroline Issa, who was frequently a subject outside of fashion shows, agrees. “Like the best documentary photographers he knew how to be unobtrusive, with that gentle winning smile,” she said.

Arguably, this is the way he got the pictures he got – ones that have their subjects smiling too, or going about their daily business. Cunningham was determined, but charming with it. Rebecca Lowthorpe, fashion director of Grazia, said: “The way he operated was more like a war photographer, in that nothing would ever stop him from getting his shot.”

He started photographing stylish passerbys in the 70s for weekly On the Streets pages in the Times, and applied the same democracy to his fashion pictures. His pages would include the familiar street style favourites – the Vogue’s three Annas, Piaggi, Della Russo and Wintour, who famously quipped: “We all get dressed for Bill.” But they were just as likely to feature unknowns as well as shots of shoes, handbags and, quite often, dogs. “It didn’t matter who you were, so long as you were wearing something in such a way that caught his eye,” said Lowthorpe. “I think a lot of photographers now make the street style scene look a bit serious and untouchably cool, like ‘You can’t sit with us,’” said Kenya Hunt, the American-born fashion features director of UK Elle. “But Bill always made it look fun.”

By the time of his death, Cunningham was recognised outside fashion shows for his uniform of blue worker’s jacket, khaki chinos, bicycle and camera always held up to his eye – he almost became a celebrity in his own right. To have your picture taken by him was a badge of honour. Hunt had a her picture taken by him a “few times. The first was just my feet, but I was still like ‘Boom, I made the cut!’” Another time saw Hunt part of a bigger feature on editors wearing coats wide open in the dead of winter. “His commentary always had this wry, relatable humour to it,” she said. “He loved fashion, but could make fun of it as well.”

It’s indisputable that Cunningham was a pioneer of street style photography – the kind that grew up in the 80s but has become now commonplace in fashion media in the past 10 years. Other names like the Sartorialist’s Scott Schulman and Vogue.com’s Tommy Ton owe a lot to his work, and Lowthorpe calls him “the grandfather of street-style photography”. But to mistake that as a cosy presence is to underestimate a steely, determined character as seen in the 2010 documentary Bill Cunningham New York. This award-winning film that made him a hero to a younger generation. Gigi Hadid and Rihanna both posted tributes on Instagram, with the singer commenting: “We gon’ miss you in dese streets!!!”

Cunningham famously tore up cheques from the New York Times in order to maintain creative freedom, and was riding his bike and attending shows until this year. Suzy Menkes, who worked as a fashion critic for all of the time Cunningham was outside those shows, offered insight. “At age 87, Bill Cunningham was still cycling around New York, refusing my offer to share a taxi, even when it snowed,” she wrote on Instagram. “May he rest in peace, but his incomparable record of changing styles last forever.” Ultimately, Cunningham was almost like an anthropologist of fashion. He said “the best fashion is on the street – always has been, always will be.” His legacy is that other people now know this too.