Bill Cunningham, the photographer loved for his long-running coverage and commentary on street fashions for the New York Times, is also a cultural anthropologist and an architectural historian. All of his interests combined in an eight-year project called Facades, now on view at the New-York Historical Society.

In the late 1960s, when Cunningham began work on Facades, New York was in a municipal financial crisis that wreaked havoc on daily existence, with crime, drugs, and garbage seemingly overtaking a city that had lost the ability to manage. But it was also a period of great creativity, when artists and musicians experimented with new forms of expression.

While Cunningham’s photographs offer a clear-eyed view of the tough cityscape during this chaotic time, his vision was part of a larger movement towards preserving the historic heritage of the built environment to improve the quality of urban life.

Above: Bill Cunningham, Guggenheim Museum (built 1959). Editta Sherman wears an ensemble that would suit a jet-setter at the time the Guggenheim opened its doors.

As artists and musicians were staking their claim on the abandoned factory buildings of what was to become Soho, further uptown, Cunningham and his neighbor and fellow photographer, Editta Sherman, joined forces. Together they scoured flea markets, thrift shops and auctions to find period costumes for Editta to wear. Cunningham placed his model and muse in settings where the architecture became a contemporaneous backdrop for the fashions.

Some of the flourishes were created by Cunningham, who had previously worked as a milliner. In his photograph of Editta at Grand Central Station (above, left) the confection of rose, feathers and leaves atop her head echoes the intricate carvings that surmount the terminal’s clock. In another photograph, one has to wonder if a feathered muff, which on close inspection takes the form an entire duck, is of his making. Of the 500 period costumes he assembled, only one was 100% intact, and Editta, dressed as a Revolutionary war-era dandy, wore it to pose in front of St. Paul’s Chapel (built ca. 1766-1796), the oldest surviving church in Manhattan. (above, right).

The series, which begins with the Colonial era, concludes with the Swinging 60s, and Editta sporting a Courreges outfit, complete with the white patent leather boots and a pillbox hat. Along the way, one can also appreciate Cunningham’s love for black-and-white photography, and his progress from a journeyman printer, whose burning and dodging is evident, to a master.

His aesthetic, which echoes the look of the great Modernist architectural photographer Ezra Stoller, relies on a perfect negative to render every shade of gray across the spectrum, along with highlights in the shadow areas. Naturally, a model wearing a light-colored dress will pose problems. So for anyone nostalgic for the darkroom, this exhibition offers yet another area of interest.

Cunningham and Sherman often traveled to locations by public transportation to avoid wrinkling the costumes, and Editta Sherman on the Train to the Brooklyn Botanical Garden (above, ca 1972) captures the jarring juxtaposition of Sherman sitting primly in a graffiti-covered subway car. All photographs © Bill Cunningham, New-York Historical Society, Gift of Bill Cunningham.

Bill Cunningham: Facades, on view March 14-June 15, 2014. The New-York Historical Society, 170 Central Park West, at 77^th Street, NY, NY. Information. On April 16 at 6 pm, there will be a screening of the award-winning documentary Bill Cunningham’s New York. Information.