Bill Cunningham — the esteemed New York Times street-style photographer, 80-something bike enthusiast, and big-smiled living legend — has dug deep in his own archives for a series of unusual photographs he took between 1968 and 1976, which will soon go on view at the New York Historical Society.

The photos are unusual for their conflation of periods and styles; they was not intended to be a fashion shoot, but an impossible conversation, if you will, between various eras in the city’s history. Cunningham, a former milliner, pairs his model (his neighbor at the time, Editta Sherman) dressed in the period costume — comprised of vintage and thrift store finds — with matching architecture. Hence the name of project, Façades.

It should be noted that this span of eight years was not a particularly glitzy period for the city, but a time when its luster was in serious decline. The city nearly went bankrupt in 1975, around the time of one particularly arresting image from Cunningham’s series that shows Editta gussied up — complete with a large opera-style hat — and sitting rather uncomfortably in a subway car riddled with graffiti. It’s a jarring stylistic mismatch, the only image in which Cunningham allowed the city’s grit to creep into the frame.

Façades, March 16 – June 15, 2014, New York Historical Society, 170 Central Park West (at 77th Street)