As avid followers of her career will know, Anna Wintour was the fashion editor of New York Magazine from 1981 to 1983, prior to heading to Vogue as creative director. During her time at the magazine, she covered fashion in all its contexts — blending the worlds of high society, art, and industry insiders into her pages. Her fashion shoots are a who’s who of ‘80s luminaries, from Jean-Michel Basquiat to artist and society fixture Beatrix Ost to Ines de la Fressange, who models in a spread that features models off-duty before the term was even coined. (The 25-year-old Fressange’s off-duty outfit? In her words, a “cheap” Hanes T-shirt and fake pearls that are “very Chanel.”)
The pages are also a testament to the cultural moment that was the early ‘80s. Danceteria couldn’t have been a more era-appropriate setting for a nightclub-themed feature titled “Wait Until Dark.” A spread on power suits, for “women in the foreground,” offers a proto–Lean In vision of female CEOs. In other corners, quirky, childlike style ruled: “Witty hats and funny flats” anchored a paper-doll-themed special on spring fashions. And doormen, firemen, construction workers, baseball players, and hot-dog vendors were conscripted as male models for a lighthearted shoot. Click through the slideshow to see all the spreads.