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Bill Cunningham, the street-style photographer whose photo essays for The New York Times memorialized trends ranging from fanny packs to Birkin bags, gingham shirts and fluorescent biker shorts, died in New York on Saturday. He was 87.

He had been hospitalized recently after having a stroke. His death was confirmed by The New York Times.

In his nearly 40 years working for The Times, Mr. Cunningham operated both as a dedicated chronicler of fashion and as an unlikely cultural anthropologist, one who used the changing dress habits of the people he photographed to chart the broader shift away from formality and toward something more diffuse and individualistic.

At the Pierre hotel on the East Side of Manhattan, he pointed his camera at tweed-wearing blue-blood New Yorkers with names like Rockefeller and Vanderbilt. Downtown, by the piers, he clicked away at crop-top wearing Voguers. Up in Harlem, he jumped off his bicycle — he rode more than 30 over the years, replacing one after another as they were wrecked or stolen — for B-boys in low-slung jeans.

In the process, he turned into something of a celebrity himself.

In 2008, Mr. Cunningham went to Paris, where the French government bestowed him with the Legion d’Honneur. Back in New York, he was celebrated at Bergdorf Goodman, where a life-size mannequin of him, as slight and bony-thin as ever, was installed in the window.

In 2009, he was named a Living Landmark by the New York Landmarks Conservancy and profiled in The New Yorker, which described his columns On the Street and Evening Hours as the city’s unofficial yearbook, “an exuberant, sometimes retroactively embarrassing chronicle of the way we looked.”

In 2010, a documentary film, “Bill Cunningham New York,” premiered at the Museum of Modern Art to glowing reviews.

Yet Mr. Cunningham told nearly anyone who asked about it that the attendant publicity was a total hassle, a reason for strangers to approach and bother him.

He wanted to find subjects, not be the subject. He wanted to observe, rather than be observed. Asceticism was a hallmark of his brand.

He didn’t go to the movies. He didn’t own a television. He ate breakfast nearly every day at the Stage Star Deli on West 55th Street, where a cup of coffee and a sausage, egg and cheese could be had until very recently for under $3. He lived until 2010 in a studio above Carnegie Hall amid rows and rows of file cabinets, where he kept all of his negatives. He slept on a single-size cot, showered in a shared bathroom and, when he was asked why he spent years ripping up checks from magazines like Details (which he helped Annie Flanders launch in 1982), said: “Money’s the cheapest thing. Liberty and freedom is the most expensive.”

His uniform was utterly utilitarian: a blue French worker’s jacket, khaki pants and black sneakers. Although he sometimes photographed upward of 20 gala events a week, he never sat down at any of them for dinner and would wave away people who walked up to him to inquire whether he would at least like a glass of water.

Instead, he stood off to the side photographing women like Annette de la Renta and Mercedes Bass in their beaded gowns and tweed suits. As Anna Wintour put it in the documentary about Mr. Cunningham, “I’ve said many times, we all get dressed for Bill.”

Mr. Cunningham’s position as a perennial outsider among a set of consummate insiders was part of what made him uniquely well suited to The Times.