By presenting fashions in the context of New York City architecture, Mr. Cunningham traces the evolution of aesthetics from colonial times to the rise of Modernism. On the surface, “Facades” seems to be a lark. There’s something very light, even madcap, in this historical dress up, but behind it, there looms serious intention. “Facades” was begun not long after the demolition of Pennsylvania Station, the McKim, Mead & White masterpiece that still haunts the city’s memory. The obliteration of Penn Station was the most dramatic example of a process that has plagued New York from its earliest days, the destruction of the city’s greatest buildings — including the Garden at Madison Square, the Vanderbilt Mansions, the City Hall Post Office, Colonnade Row and the old Waldorf-Astoria hotel — driven by the irresistible force of property values. In 1965, the New York City Landmarks Preservation Commission was founded to fight the loss of the city’s architectural heritage and one can’t help seeing the case for preservation in these photographs.

Ms. Sherman is a wonderful model for the clothes, adapting her hair, makeup and posture to each period with playful accuracy. She acts the part required by each ensemble and brings the spirit of the time to each, whether she’s in petticoats, bustle and bonnet or in a swinging ’60s mini. She fills the bill as a lavishly attired belle époque society matron, with great presence and attitude, but when the outfit required it, she could conjure up a Twiggy moment. In “Facades,” Mr. Cunningham shows that he is far more than a snapshot photographer. His compositions maximize the interplay between fashion and architecture. Ms. Sherman’s fur pillbox hat perfectly punctuates the daring shape of Frank Lloyd Wright’s Guggenheim Museum. The fantastical bonnet of flowers and feathers she wears posing in front of Grand Central Terminal echoes the drama of Jules-Félix Coutan’s sculpture of Hercules, Minerva and Mercury atop the clock on the facade.

While many of Mr. Cunningham’s photos seem to transcend time, others toy with it. In otherwise pristine period portraits, the present intrudes now and then as an anachronism. An early 1970s taxi interlopes on the stylish ’20s Gothamite posed in front of the Racquet and Tennis Club built in 1918. And as the chic 1940s lady, Ms. Sherman, in fox furs, a camellia-adorned hat and white gloves stands in front of Isamu Noguchi’s “News” frieze at the entrance to the Associated Press Building at Rockefeller Center, where a puzzled tourist from the 1970s looks on as if she’s just stumbled into a temporal vortex. The New-York Historical Society exhibition incorporates numerous charming notes that Mr. Cunningham inscribed with pencil on his prints in verso, such as this one from a surprisingly sexy shot of a translucent turn-of-the-19th-century gown in which the model’s body is silhouetted by the sun through the gauzy fabric: “The gowns were worn over pink body stockings or sheer slips. The custom of the French ladies to immerse themselves in a tub of water when fully dressed so the gown would stick to the body, caused an epidemic of influenza and many thousands of deaths that was called the ‘muslin disease.’ ”

The “Facades” project was completed 37 years ago, and it surveys almost two centuries of fashion and architecture, but the photographs appear as a breath of fresh air at a time when commerce dominates culture and fashion is almost a religion. Bill Cunningham is not an innocent, but he is a rare purist, and this body of work is a testament to his undiminished idealism. The Cunningham philosophy of fashion is remarkably egalitarian, and it is something that every contemporary participant in fashion should take to heart: “Fashion is the armor to survive the reality of everyday life. I don’t think you could do away with it. It would be like doing away with civilization.”