“The vibrant worlds of art and fashion help make the city great, but they rarely meet — except at gallery openings,” wrote Anna Wintour in the magazine’s August 29, 1983 issue. “What kind of sparks would be given off, we wondered, if we caused those two worlds to collide?” For the accompanying feature titled “Painting the Town,” she got prominent artists like Jean-Michel Basquiat, David Salle, Alex Katz, and Red Grooms to make paintings especially for the shoot — an art-and-fashion juxtaposition that was rare at the time. The custom canvases accompanied designs by Mary McFadden, Oscar de la Renta, and Calvin Klein, among others.
It wasn’t her only notable use of artwork — soft, Deco-style illustrations also decorated a new-designers feature and a multipage spread on the season’s new bathing suits. Click through the slideshow to see all the art-focused spreads from Wintour’s years here.