Said outfit, of course, echoed her on-screen style as Annie, whose “rueful, Chaplinesque, baggy-pants-and-vest look” struck a chord with an entire generation keen to leave behind the “rich hippy” feel of the late ’60s, as Vogue put it. The key to achieving the aesthetic? In a word: vintage.
“Even before the emergence of the Annie Hall style, the popularity of thrift shop clothes had hit the streets,” this magazine noted in an August 1978 interview with the film’s costume designer Ruth Morley. “Ethel Scull made the papers in New York a few years back when she appeared at a gathering of swells in a genuine ESSO workman’s coverall, and rock stars had popularized the slightly schizophrenic garb of cast-offs from other milieux. Lifestyles in general have grown less formal by quantum leaps, and individuality in clothing seems to be a badge for that by-now clichéd adage to ‘do your own thing.’ Women’s hard-won independence is reflected by their search for more personal and less dictatorial styles.”
For her part, Keaton had been a devotee of Goodwill since the early ’60s, calling its LA branches her “sanctuary” as a teenager. “Mom taught my sister Dorrie and me to rummage for the best and alter if needed,” she wrote in Fashion First. “Someone else’s junk was now our perfect treasure. Once home, we would put together outfits for the rest of the day, while discussing when we would go back to the Goodwill.” Before she had even left Santa Ana College for Manhattan, she had developed her distinctive taste—as evidenced by her request to wear a bowler hat to her prom. “My mother said, ‘Maybe another time, Diane.’”
Here, Vogue looks back at the star’s most memorable early fashion moments.