Embrace Androgynous Style With A DIY Annie Hall Halloween Costume

Sure, you could cover yourself in green body paint and don a black leather get-up in hopes of channeling Guardians of the Galaxy heroine Gamora this Halloween, but chances are you’ll encounter dozens of similar costumes inspired by the sci-fi character, making you feel like all that hard work was for naught. To stand out from the crowd, look to an even more iconic film character for inspiration: Annie Hall.

Perhaps no woman in motion picture history has rocked a bowler hat and wide-legged trousers with as much flair as Diane Keaton in Woody Allen’s 1977 romantic comedy Annie Hall. To this day, she is credited with popularizing the androgynous, borrowed-from-the-boys aesthetic that’s ubiquitous in today’s fashions.

Not only will a DIY Annie Hall costume help you flaunt your style acumen and near-encyclopedic knowledge of American cinema, but it will be a worthy investment since, given the popularity of gender-bending looks, the individual elements of your costume could very well be repurposed into a workplace-ready ensemble.

Start with the basics: a crisp white collared shirt like the Jaclyn Smith French cuff blouse and a pair of khaki trousers like the Jaclyn Smith twill pants. Next, infuse some masculinity into the look via the black satin David Taylor Collection clip-on necktie and the Attention button-front vest, featuring a single button closure and three decorative welt pockets. Complete the look with a fitted brimmed hat like the Bongo leopard print fedora.

Come Monday, ditch the clip-on tie and fedora (sorry, Halloween is over!) and layer on a blazer or motorcycle jacket for an added masculine but chic addition. As for your shoes, keep it casual with work-appropriate heels or keep it comfortable with patent loafers.

Now that your costume’s ready, all you have to do is practice those Annie Hall “La-dee-das”!

Shop the Look:
Attention Button-Front Vest
Bongo Leopard Print Fedora Hat
Jaclyn Smith Twill Pants
Jaclyn Smith French Cuff Blouse
David Taylor Collection Men’s Clip-On Necktie


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