Updated: Annie Hall And Shopping Menswear: A Love Letter

“In 1978 in Nairobi, I got this bag,” said New Yorker writer Judith Thurman. “I got it because it was Annie Hall’s bag.” What is it about the title character of Woody Allen‘s romantic comedy classic that continues to captivate?

Thurman was speaking at the New School to kick off a new series of free screenings of fashion-related films, each introduced by a prominent writer. More than 30 years after it was made, Annie Hall continues to delight audiences — and the men’s clothing Diane Keaton sports in nearly every scene continues to influence how we dress.

Thurman, a native of the city, reminded the audience that the film, set in the mid-70s in New York, was a portrait of a city that was then nearing bankruptcy. (In 1975, Mayor Beame even prepared a public statement to announce “the default we have struggled to avoid” and President Ford refused a request for a federal bail-out, but the teachers’ union pension fund made a last-minute $150 million investment in municipal bonds that kept the city solvent.) Crime and social disorder were high; “Everyone you knew had been mugged,” said Thurman. “Your television was kind of on loan until it was stolen.”

This wider context is only briefly mentioned in the Annie Hall — as they’re about to play tennis, comedian Alvy Singer tells his actor friend Rob that he’s sure the city isn’t getting federal help because of anti-semitism. “The rest of the country looks upon New York like we’re left-wing, communist, Jewish, homosexual pornographers,” he exclaims. But the experiments in creativity going on in New York at the time are written all over this talky, fourth-wall-breaking, genre-bending, unapologetically smart movie.

And, oh my, the clothes. That scene where Annie, dressed again after the tennis match where she meets Alvy, emerges in her loose khaki pants, man’s shirt, waistcoat that unbuttons to reveal a wide tie, her hat framing her face, her sisal tote bag slung over her shoulder — that is the scene that launched a million ill-advised teenaged girls’ attempts at men’s wear. (Including my own. I didn’t have a waistcoat, so I used a cable-knit sweater vest and wore a pair of my father’s pants that happened to be glen plaid.) Not to mention a million Polyvore guides. This one is about right, except in the film, it is Annie’s copy of Ariel that draws Alvy’s sarcastic ire, not The Bell Jar. (Sorry, I’m an incorrigible nerd.)

Something about the idea of buying a head-to-toe “Annie” look doesn’t sit right with me. Not because it’s cheating — Annie certainly likes to shop; after yet another date to see The Sorrow And The Pity she asks Alvy, “Sometimes I ask myself how I’d stand up under torture,” and he replies, “You? You kiddin’? If the Gestapo would take away your Bloomingdale’s charge card, you’d tell ’em everything” — but because Annie Hall’s is such a personality-driven and specific sartorial expression. Anyone can buy the item of clothing we have so patronizingly come to call a “boyfriend blazer” off the rack, and many members of the audience last night had on some version thereof, but I’m well aware that wearing one doesn’t make me Annie Hall. And what so many modern recreations of her style miss, in the tightening of the cut or the elision of gendered details like ties, is that the look is meant to be in resistance to the conventional metrics of female attractiveness — it emphasizes neither breasts nor hips nor waist, and she keeps her hair mostly tied up. I’m sorry, Kate Moss, but the Annie Hall look does not include pleated khaki short shorts.

Annie Hall’s aesthetic is one of refusal: a refusal to acknowledge or play up a woman’s stereotypical (and, by the 70s, dubious-seeming) “power” to seduce, a refusal of sexuality, and, Thurman pointed out, “of all the commitments that come along with it.” Annie covers her body in layers of fabric. When Alvy tells her he loves her, on South Street practically underneath the Brooklyn Bridge, she has on a capacious ankle-length skirt — actually, it might be two skirts — man’s houndstooth blazer, a hat, a scarf, and boots. Her pants are cut billowingly wide, and even when she sings in a nightclub, the only concession she makes to the context is to leave the top button of her white collared shirt undone. This is the decade of feminism’s second wave, and her look, I am certain, is an outward indication of ideological convictions about the place of women in society that her character holds. If you don’t share those convictions, that confidence, then even the most faithful recreation of her digs will just be costume. In a way, to be Annie Hall, you have to be Annie Hall. That proposition is inherently untenable.

And yet, in various forms, her look remains a popular fashion touchstone. Stella McCartney’s and Phoebe Philo’s aesthetics share a little bit of Annie’s unfussy, comfortable, beauty. Maria Cornejo has, in the abstract, her refusal, her power, down. More concretely, men’s wear-inspired items, like blazers, are going through a renaissance right now, although not all of us who wear them are “borrowing our banker boyfriend’s clothes,” Sally Singer. Button-down shirts are considered classics for women.

What are the elements of Annie Hall’s style? Success has many authors. Thurman, who in addition to “Annie’s bag” brought on stage a hat she picked up at a New York flea market in 1979 because “It was Annie’s hat,” aptly traced Annie’s references. Diane Keaton and costume designer Ruth Morley, who worked on iconic New York films like Taxi Driver and Kramer vs. Kramer, collaborated on Annie Hall’s look, which was heavily based on the clothing Keaton herself wore. (And, in fact, continues to wear, despite the objections of some members of the the peanut gallery.) A few pieces of clothing came from Ralph Lauren — and Annie’s look ended up epitomizing the designer born Ralph Lifschitz’s aspirational WASP-iness — but he isn’t thought, Thurman said, to have had much to do with the styling.

“There’s a strange personal semiotics of what you choose to wear in the morning,” said Thurman. Keaton/Annie’s clothing refers to a lot of sources. There’s Patti Smith, who personified “boyfriend” dressing in the early 70s in New York, when she was living with Robert Mapplethorpe in the Chelsea Hotel and wearing his blazers and shirts out. But Annie’s look is cleaner, and, though transgressive in its way, nowhere near as wild. Thurman pointed to something of Isadora Duncan in Annie’s propensity for long, wispy silk scarves. Annie is sexually repressed — her inability to relax, perhaps her guilty reaction to her own pleasure, plagues her sex life. “In a way,” said Thurman, “the scarf is a form of freedom that she tries on, in the hope that it might stick.”

And Katharine Hepburn pioneered those loose, pleated, high-waisted pants Annie wears, just as Charlie Chaplin did the hat. But above all, Thurman argued, Annie hall owes a debt to Coco Chanel, pointing specifically to a picture of Chanel on a fishing trip in Scotland in 1928, wearing a man’s shirt, jacket, tie, and pants, topped with a soft hat. “Chanel understood the ease and confidence that men’s clothing gives them, and she harnessed that for women,” she said. “That was her great contribution to fashion.”

Roger Ebert wrote, “Women put up with a lot in Allen’s movies, but at a certain point they draw the line.” In the end, Annie refuses Alvy’s plea to return to New York, and get married. She’s happier where and how she is. One of my favorite things about this movie, and part of the reason it never fails to make me cry, is the transformation Annie undergoes: from the inhibited, awkward, falling-over-her-words woman that she is at the beginning, she becomes confident and intellectually assertive. Her clothes don’t change, though. It’s more like she grows into them.

Update: There are two codas to this post. I originally wrote that “The clothes came from Ralph Lauren.” (I wrote this because there is a small credit at the end of the film to the effect of, “Clothing by Ralph Lauren.”) In fact, as one of Ruth Morley’s daughters wrote to tell me, that is incorrect. “Very little Ralph Lauren clothing was used in the film,” she said. “The tuxedo jacket Diane Keaton wore when singing, and one blazer were Ralph Lauren. A jacket or two worn by Woody Allen were Ralph Lauren. Lauren created the myth that most of the clothes used in Annie Hall were his designs. He made a fortune and a reputation from this. The costume designer Theoni Aldridge actually sued him for taking undue credit for costume design for The Great Gatsby, but my mother didn’t have the heart for that.” As for the credit line, “the film was made in the days before serious product placement, so it was what the producers negotiated with Lauren for free clothes.” The post has been updated to reflect this information.

The other coda is of much less significance, but as soon as I saved this post, I got on the subway to go downtown. At 125th St., a woman who looked to be in her 70s walked by. She was wearing wide-legged khaki pants, a brown leather belt, a loose-fitting white button-down, lace-up flats, and she had a colorful, fringed silk scarf wrapped around her neck, and as she passed me, I had the distinct thought that that is how I want to look, dress, and be when I am her age.