Editor’s Note: Delving into the archives of pop culture history, “Remember When?” is a CNN Style series offering a nostalgic look at the celebrity outfits that defined their eras.

By today’s standards, the front cover of American Vogue’s November 1988 edition seems typical enough. Beside the text “the real cost of looking good,” Israeli model Michaela Bercu gazes past the camera, her windswept hair brushing across the shoulders of a bejeweled $10,000 Christian Lacroix couture jacket.

Yet, the cover signaled a revolution at the storied fashion bible. It also marked two important — and related — firsts: This was the first Vogue cover produced by editor-in-chief Anna Wintour and the first ever to feature a pair of jeans.

London-born Wintour, who on Thursday stepped down from the role after 37 years (she will remain as Vogue’s global editorial director and publisher Condé Nast’s global chief content officer), had been hired to shake things up. The magazine’s previous editor, Grace Mirabella, oversaw a surge in readership but was, by her own admission, increasingly out of step with the 1980s zeitgeist. Condé Nast executives were reportedly worried the title was losing its edge. Mirabella had famously repainted former editor Diana Vreeland’s red office a shade of beige, which became a metaphor for her reputation as being too unadventurous.

Practically every American Vogue cover from 1980 to 1988 had been taken by Richard Avedon, a fashion photographer known for his stark, minimalist style. Models were usually shot against plain studio backgrounds in heavy makeup and statement jewelry. The covers were self-consciously elegant, standing aloof from the more mainstream women’s weeklies they shared newsstands with.