Happy Birthday, Annie Hall

Forty years after Woody Allen’s film made menswear sexy, Alexa Chung tips a hat to her tomboy muse.

- Jennifer Ferrise

Alexa Chung remembers when she first watched Annie Hall. She was 19 and living in the English countryside. She’d never been to New York City and wasn’t yet the trendsetter she’s known as now. Back then, style wasn’t even on her radar—then came Diane Keaton in a tie.

“Seeing Annie Hall was almost like being introduced to the Smiths or the Cure,” Chung says over brunch at B Bar & Grill in N.Y.C.’s East Village. “It was also the first time I’d seen someone really owning a tomboy aesthetic that didn’t take away from her femininity at all. I thought, ‘Oh, I feel like that.’ It quickly became the basis of any ounce of taste I had.”

From meet-cute to move-out, Annie Hall charts the highs and lows of a failed relationship between Woody Allen’s neurotic stand-up comedian, Alvy, and his free-spirited girlfriend, Annie, played by Keaton. Her off-kilter charm and effortless delivery earned her a best actress Oscar, while a best picture award cemented the movie as a beloved American rom-com.

Equally celebrated were the clothes. Costume designer Ruth Morley worked closely with Keaton to create Annie’s now-iconic mix of natty blazers, vests, and wide-leg trousers, inspired by what the women on the streets of SoHo were wearing in the mid-’70s. With The Mary Tyler Moore Show and Charlie’s Angels already setting the stage, Annie’s look helped propel menswear as women swear into the mainstream.