Photo via Getty

The streets felt emptied Saturday afternoon, after the news broke that Bill Cunningham would no longer be out in them, taking photographs of people and their clothing. Cunningham died at the age of 87, apparently about as well as one could have hoped—quickly, after a stroke, less than three weeks after his last set of photos had run in the New York Times.

Those photos had been of “that unbeatable combination, black and white,” as Cunningham called it in the accompanying online slideshow. “A lot of people complain about fashion, and fast fashion, and ‘There is no fashion,’” he said. “That’s baloney. Look at this! Hey, I never saw it as good as this in the 1950s.”

Cunningham had been looking, and retaining what he’d seen—mentally, and in a profusion of filing cabinets in his apartment that crowded out the ordinary accoutrements of living—all the while. Earlier in that slide show, he’d focused on a dress printed with a pattern of dresses, in “silhouettes from the nineteen fif—” He broke off and interrupted himself: “About 1955.”

Year by year, week by week, hour by hour, Cunningham was on the move in the city with his eyes open and his camera out, witnessing and reporting what people were saying to one another, and about the world, with their clothes. You saw, say, bare shoulders on Fifth Avenue in May, and Cunningham put bare shoulders (“the first summery trend”) on Fifth Avenue in the Times. “Every kind of summer blouse, shirt....,” he said in his online commentary. “It’s wonderful.”

Cunningham was happy about the trend, but it was a serious happiness. His suite of eccentricities—his bicycle, his blue work jacket, his renunciations of food or money or any sort of dependence—amounted to a self-invented one-man monastic order, devout in his pursuit and examination of what he would call, on the occasions when he had no choice but to explain what it was, beauty.

His aversion to being examined himself was a running theme in the documentary Bill Cunningham New York, the rare examination to which he did—grudgingly, diffidently, cantankerously—submit. Even the New York Times, in its Cunningham obituary, had to turn to the film for reference. It was a profound and at times heartbreaking thing to watch even when Cunningham was alive and working.

The rewatching of the movie was yet more melancholy against the backdrop of Pride weekend. Cunningham’s lens championed self-expression, and particularly gay self-expression, through the years of liberation. But his own austerity was shaped, unavoidably, by an older culture, one of constricted possibility. When the question of his personal life comes up, very late, in the movie, he appears to engage with it directly–only to rush past it, to talk instead about what the idea of his possibly being gay might have meant to his working-class Irish Catholic family. First he made ladies’ hats, then he took fashion photos, and with those things he created a space in the world into which he could fit himself.

Through his work, he embodied, as so many things are supposed to but so few do, the potential of the city. To cross paths with Bill Cunningham was to feel a real thrill, the endless mundane unfolding of the present transformed to the flash of the Now. There are bare shoulders out on Fifth Avenue today, and black-and-white prints, and the iridescent flash of a detail on a bike messenger’s shoes, but there is no more chance of seeing Cunningham seeing them, and New York is a diminished place for that.

Surely, plenty of street photographers and party photographers are working even now, if not with Cunningham’s particular journalistic rigor. There are uncountable people taking pictures of themselves, in their clothes. We are alive in a moment of endless self-documentation.

But: I have, piled up on my phone and my computer, hundreds or thousands of snapshots of my own children. Last summer, though, in a crowd of tens of thousands at the Philharmonic in the Park, my younger boy was climbing up a metal barrier when a blue-coated figure, passing by, stopped and snapped his photo. It never appeared in the paper, and it never mattered. The boy was there, and Bill Cunningham saw him.