Working Titles – Annie Hall

Blurring between male and female sartorial norms is commonplace in 2022, but Woody Allen's Annie Hall stuck was revolutionary back in 1972.

Brad Lanphear |  January 12, 2023

Annie Hall is among the most realistic portrayals of romantic relationships in the history of cinema. Woody Allen’s 1977 masterpiece is often misrepresented as a Romantic Comedy but the film’s grasp of the human condition expands far beyond the confines of that category.Love, romance, and even human connection on the simplest emotional levels are far more complicated than Hollywood suggests. Romantic Comedies are essentially escapist entertainment to distract audiences from the absurdities, disappointments, and frustrations of real romance.With Annie Hall, Allen places those realities front and center, forcing the audience to grapple with them just as his character, Alvy, does. 

Alvy in his M65 jacket as he and Annie wait in line for a movie. Image via United Artists.

The reason Annie Hall feels so accurate as a snapshot of a romance is that the film was not originally intended to be about the relationship between Annie and Alvy. When Allen and co-screen writer Marshal Brickman wrote the film, it followed Alvy as he unsuccessfully pursued joy in life.It was an absurdist existential romp that clocked in at just under three hours long when they made the first cut of the film. Upon viewing the rough cut, Allen and Brickman realized that the relationship between Annie and Alvy was the only cohesive story there.So the theatrical cut of Annie Hall was an actual romance edited out of a much larger story, just as it would be when recanting a real-life romance. 

Welcome to New York

Alvy and his friend Rob in 1970s tennis outfits, including tab waist shorts. Image via United Artists.

Along with brilliantly capturing the nuances and imperfections of romance, the film also captures New York City (and briefly Los Angeles) of the late 1970s in a much more candid way than other contemporaneous films. Each scene feels more like a home movie or even a personal memory than a proper film.This was a very intentional feeling achieved through cinematography and wardrobe. The camera acts as a stand-in for the viewer as if it were actually a participant in the film, with Allen, and occasionally other characters, talking directly to the camera.  

Alvy only wears one belt throughout the entire film. Image via United Artists.

The wardrobe for the film was meticulously assembled to represent the Upper East Side of Manhattan during the late 1970s. Every neighborhood in New York City has its own distinct vibe in the way people dress, talk, act, and socialize.This is true today and it was certainly true in the 1970s. Allen was born in Brooklyn but has lived on the Upper East Side for most of his life. Annie Hall is not only set predominantly in this specific neighborhood at this specific time but the wardrobe and characters are intensely informed by it.

Keaton’s Closet

Annie playing tennis. Image via United Artists.

The lone exception to that meticulous wardrobe vision was Annie herself. Every article of clothing worn in every scene by Diane Keaton’s titular character came from the actress’s own closet. Allen was so enamoured by Keaton’s personal style that he told the wardrobe department to let her dress in her own clothes for the entire movie.Keaton’s personal clothing and styling choices became one of the most iconic character wardrobes in cinema history. Not least of all for the fact that almost everything she wore was an interpretation of menswear. 

When both the audience and Alvy first meet Annie, she is playing tennis in a men’s button-down dress shirt. The front is halfway unbuttoned, the sleeves are rolled up, and the collar is popped.This adoption of menswear in a way that expresses her feminine physique without being overtly sexual defines nearly every single look Keaton assembled for Annie throughout the film. That first shot of Annie alludes to the fundamental philosophy of her style for the entire film. 

Annie’s unique style is emphasized in this introductory scene by what her friend — Alvy’s friend’s girlfriend — is wearing. She has on an all-white halter top dress with a short skit, a typical women’s tennis outfit for the time. You would think that this juxtaposition of Annie’s dress shirt and short, boxy shorts would make Annie look like a tomboy – but it has the opposite effect.Keaton carries herself with such a strong feminine virtue that the audience loses sight of any ‘gender norms’ her outfit is breaking. Annie has the allure of a confident woman and her friend comes off looking overtly girly. 

Annie’s Vibe

Annie in her most iconic outfit, also with a cool tote. Image via United Artists.

The tennis scene is very brief and the nuances of Annie’s wardrobe are easy to miss upon first viewing. It is the subsequent two scenes that showcase the most iconic outfit of the entire film: Keaton’s styling of Annie in wide-leg khaki chino, a white pointed collar dress shirt, black vest with only the top button done, and broad blue pin-dot tie, topped off with a black wide brim hat (above).

The pants are huge, which was the style for men at the time but not women, and the shirt is a bit oversized though the sleeves and neck are tailored perfectly. The vest is the critical element because it holds the shape of Keaton’s figure enough to prevent it from drowning in the shirt and pants. 

Annie in a khaki suit dancing with Paul Simon in an Aloha shirt. Image via United Artists.

There is very good reason that this is the outfit people inevitably associate with 

Annie Hall.

 It is the outfit that women wear for Halloween as Annie. It is the outfit Keaton is wearing in the shot chosen for the movie’s poster.

This outfit represents Keaton, and therefore Annie, owning menswear in a way that no other man does in the film. She has the effortlessly cool factor that everyone strives for when they style themselves. Her look is not derivative of anything yet it consists of common clothing items.

The way she assembled them and the way she carries herself in them creates a totally unique vibe. 

image via The Boston Globe

It is also worth pointing out how cool Annie’s tote bag is in this scene. It appears to be a light rattan, maybe hemp canvas. The khaki color with red dashed horizontal stripes looks like something you would only find from a Japanese brand these days.This makes sense since they heavily draw inspiration from 1950s-1970s American aesthetics exhibited so well in this film. Keaton probably picked this bag up from some small shop in New York and it was probably made in America during the mid-twentieth century. 

Alvy and Annie

Annie and Alvy wearing the same tweed blazer. Image via United Artists.

A running theme throughout the film, which is often overlooked upon first viewing, is that Annie burrows Alvy’s clothes and always styles them better than he does. As their relationship progresses, she starts to wear more and more of his stuff, building her ‘male’ fashion collection off of him. Alvy wears tweed blazers throughout the film, often over plaid shirts.When Alvy and Annie attend a party, she’s wearing the blazer he wears during the opening monologue. She pops the collar, wears it open, and styles it with a long scarf. During another scene where the couple walks along a beach in the Hamptons, she is wearing one of his blazers.  

Alvy in his look and Annie copying his look. Image via United Artists.

Keaton’s reinterpretation of Alvy’s jackets for Annie demonstrates just how much personal touch can dictate whether an item looks cool or not. Alvy’s jackets look professorial on him while they look sexy on her. Annie’s absorption of Alvy’s look reaches the point where she wears a head-to-toe copy in the scene where the couple shop for books. The context of this is important because Annie goes through a period in their relationship where she wants to be as educated as Alvy and attempts to read the books, watch the movies, and take classes that Alvy talks about. This ends up backfiring and making her miserable. After she rejects this pursuit, she falls back into her own style. 

Alvy in a chambray workshirt and jeans. Annie in a tee and cargo pants. Image via United Artists.

Alvy in double-pleated cord pants. Image via United Artists.

Alvy’s wardrobe is simple but respectable. He almost always wears button-down shirts but they’re 

nice

 shirts. His blazer collection is nice and the 1970s-era tailoring — wide lapels, boxy shoulders — is very much back in style now. His big, baggy 1970s pants have also come full circle, too.

In the scene where he walks down the street asking strangers about their sex lives following a fight with Annie, he wears a pair of super wide, double-pleated cords that would fit right into most menswear editorials these days. And the M65 jacket that he wears in multiple early scenes is obviously an absolute menswear classic. 

Annie in her own M65 jacket on the flight home. Image via United Artists.

It’s the respectable simplicity of Alvy’s wardrobe that allows Annie’s looks to shine. Alvy clearly has good taste but he is too neurotic and insecure to be as sartorially adventurous as Annie. Whereas Annie is bold and free-spirited in her self-expression. She may lack confidence in her intellectual acumen but she is in many ways an artist, and her style shows it.Even as the couple’s relationship is reaching its conclusion, Annie has obtained her own olive drab military jacket that she wears on their flight back from LA (pictured above). At first, I thought this was Alvy’s M65 from earlier in the film but upon closer inspection, it is a different jacket. This makes more sense given the context of their relationship at this point.

Scarf Game: 1000

Alvy in a madras shirt. Annie wearing a scarf over a dress shirt and vest. Image via United Artists

Keaton does a brilliant job of styling men’s clothing, though mostly women’s clothing copied from men’s designs, to fit her and express Annie’s vibe. So much of the success of Annie’s look comes from Keaton’s own beauty and self-confidence. The fact that most of the pieces came from her own wardrobe obviously helped her express that confidence.

However, there is one secret ingredient that Keaton utilized throughout the film to add a touch of flair to her looks: scarves. Keaton, and therefore Annie, has an impressive collection of scarves that she styles in different ways to centerpiece her outfits. 

Annie wearing a red tartan scarf over a tweed vest and trousers. Image via United Artists.

In one scene, Annie ties a scarf around the popped collar of a dress shirt like it is a tie. This is an interesting touch because men’s neckties evolved from the same neckerchiefs that modern scarves have. In another scene where Annie sings at a lounge function, she has a long black silk scarf wrapped around her neck like a choker then tied up loosely hanging down the middle of a dress shirt unbuttoned ¾ of the way.Then, in a late scene where Annie and Alvy are dividing up their stuff, she is wearing a red tartan wool scarf draped over a tweed vest and trousers (pictured above). These are just some highlights because she wears a scarf over half of the scenes in the movie. 

Gender-less Fashion

Alvy in a sweater vest and plaid shirt, Annie in a cowboy themes shirt and vest. Image via United Artists.

Annie’s wardrobe may be cool and inspirational now, looking back from the 2020s, but it was revolutionary to be featured in a major motion picture in the 1970s. Annie Hall was filmed while there was a major social movement happening worldwide to promote women’s rights, whereby many women wore traditionally men’s clothing as a sign of protest against oppressive social constructs. The idea of Annie’s wardrobe would have gotten the movie shut down less than a decade earlier. This demonstrates how much things changed in that short period of time because it was received as refreshing, liberating, and unquestionably cool when the movie came out.

Gender fluidity and the breakdown of gender labels altogether have become somewhat common in the fashion industry today, but it is very unlikely that a day will come when brands just don’t label their clothing by gender or even have a single design team making all their clothes.From a pragmatic standpoint alone, the gender divide is useful in fashion design and retail. However, fashion has evolved to a point where the lines have blurred between what makes an item male or female beyond fit. Annie Hall will always stand as an iconic beginning of that evolution. 

Alvy wearing a great trench when he sees Annie for the last time. Image via United Artists.

Get the Annie Hall Look

Buzz Rickson’s BR11702 M-65 Field Jacket, ~$405 from 

HINOYA

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Single-Breasted Jacket In Tweed – Brown Fauna Houndstooth, €1100 (~$1180USD) from 

Husbands

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Kiriko Original Scarf Kiji Indigo Checkered Multi Patchwork and Plum Blossom, $82 from Kiriko.

Stevenson Overall Co. 6 oz. “Dominator” Chambray Workshirt, $182.45 (on sale) at Corlection.

Doubke-Pleat Corduroy Pants, $268 from Noah.

Mister Freedom Berkeley Shirt NOS Madras Plaid, $290 ($261 for Heddels+ members) from Clutch Cafe.

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