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 womenswear into the mainstream.
Shot at locations ranging from Central Park to Coney Island, Annie Hall also romanticized New York for anyone who dreamed of moving there one day, including Chung herself. “It all seemed so exotic to me,” she says. “Even if I didn’t know it then, the film added to the tapestry of allure that compelled me to come to the city. I think it must have seeped into my subconscious and pulled me this way.”
By the time she finally made her move, Chung was 25 and no longer a fashion novice. After a few years of modeling and hosting TV shows in the U.K., she crossed the Atlantic to front MTV’s pop-culture variety show It’s On with Alexa Chung. Bringing a borrowed-from-the-boys way of dressing—think Annie’s striped button-downs with cutoffs and Chelsea boots—Chung established herself as a fashion trailblazer in her own right.
In her 2013 book, It, Chung wrote about her connection to the film, saying she still references it when she’s getting dressed. “She just looks cool as f—,” says Chung, now 33, with a shrug. “Good style is undeniable. If you look at what she wears—the men’s brogues, the vests—individually they’re all incredibly classic and even quite fuddy-duddy. But it’s the arrangement that makes them feel new. She’s playing with hats. She’s playing with proportion. And it’s got a touch of wacky art mum because soft bohemian pieces are mishmashed with sharp tailoring.”
It’s hard for Chung to settle on her favorite look, but if forced to choose, she likes the signature white shirt, vest, polka-dot tie, and high-waist khakis. “It’s got that je ne sais quoi,” Chung says. “That la-di-da attitude.”
That was the ensemble on Chung’s mind last year when she bought a tie from Ralph Lauren, coincidentally the same designer who made Keaton’s in the film. “When I found it, I thought, ‘Maybe it’s time for me to do the Annie Hall look,’ ” she says. “You know, capitalize on the menswear trend. But the tie hasn’t emerged yet because I don’t have a vest.”
That may be the only thing she doesn’t have. “If you said, ‘Run home and put on at least three of her outfits,’ I could throw them together, like, right now,” she says, snapping her fingers. “I mean, everything I own from A.P.C. makes it a bit too easy. I’ve got blazers ahoy, including an old hounds-tooth Aquascutum one that looks just like hers. And I have cowboy boots like hers from a shop called Back at the Ranch in Santa Fe. They’re the real deal.”
The movie has infiltrated Chung’s creative process too. After sold-out collaborations with AG, Madewell, and Marks & Spencer, Chung is launching her own fashion label this May, and while she won’t reveal much before it drops, it’s safe to say that Annie herself would approve. “I am one big nod to menswear, so it can’t help but leak out of me,” Chung says. “And I’m so sorry about that unfortunate visual.”
For more stories like this, pick up InStyle's April issue on newsstands and available for digital download March 17.
Photographer: Matthew Sprout/Exposure NY; hair: Holly Mills/Streeters; makeup: Justine Purdue/Streeters; fashion editor: Alexa Chung; manicure: Gina Edwards/Kate Ryan Inc.; production: First Light Productions.