HBD, Diane Keaton! Dictating worldwide fashion sensibilities since 1977.



OG Annie Hall: Defining the Style of an Entire Generation

If Madonna was queen of all things ’80s, Annie Hall reigned as her ’70s predecessor; unwavering in her California roots and partial to anything labeled “Men’s,” she quickly became the tastemaker of an entire generation. Forty years later (and on her birthday, not coincidentally), we’re still looking to Diane’s most famous character for the totally transcendent style of Annie Hall.

In celebration of Diane’s 71 years of low-key style androgyny, and Annie’s apparent inability to age/lose any relevance whatsoever, we’re looking back at some of the most defining style moments brought to life in the 1977 film. Tomboys, rejoice!

Men’s Ties

Homage to Annie Hall starts with the smallest of accessories—the men’s tie. Tiny but mighty, the tie makes no mistake about this gal’s intentions: she’s all tomboy, all the time. No complaints here. annie-hallThe Famous Hat

Annie Hall took one of the most prominent accessories of a man’s closet—the bowler hat—and threw it headfirst into her wardrobe with gusto. It never left—Diane adopted it as her signature look thereafter, and it’s arguably the piece that cemented her as the true queen of gender fluid style slaying.112-9714-diane-keaton-woody-allen-in-annie-hall-1459191483Clear Sunnies

In the case of eyewear, fashion surmounts practicality: while these sunnies may not be the most useful in fending off rays, they make quite the statement when Annie first starts dating Alvy (as well as later on when she makes an impromptu solo move to the West Coast). static1.squarespaceThe Upturned Collar

Before the upturned collar was synonymous with fraternity boys and the male gaze, Annie Hall owned the look both on stage and off. Paired with piled-high hair and a thin silk scarf, and she meant business. Screen-Shot-2012-08-22-at-9.01.07-PM-1024x539General Menswear-Turned-Womenswear Domination

To reiterate, no one conquered tomboy territory quite like Annie Hall. She reclaimed all that was previously off-limits, put her personal stamp on the style, and retained forever relevance from that point forward (as an actress, and, in a greater sense, as a woman who used her wit and wisdom to reshape the fashion landscape as she saw fit). So hats off to you, Diane—HBD and keep doing you. annie-hall-diane-keatonImages via Rollins-Joffe Productions

Stay tuned to Milk for more worship-worthy fashion icons we love.

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