2 Woody Allen Movies that Broke the “Rules” of Fashion

This past summer, I felt the need to watch as many old, well-known movies as I could take. I watched Breakfast at Tiffany’s, Dirty Dancing, Roman Holiday, When Harry Met Sally, and the list goes on. I think I watched about twelve classic romantic movies that Summer, but the movies that stood out to me the most were the ones by Woody Allen, which included Manhattan and Annie Hall. These two movies were the only ones that did not have some sort of lovely “living ever after” ending to them. Spoiler Alert!: they ended quite cynically. I mean in Annie Hall, Allen talked about how irrational relationships were even though we needed them to live, and in Manhattan, his 18-year-old girlfriend leaves for London after he begs her not to.

So I figure if Woody Allen makes such cynical movies that are sill so well revered today, the fashion in the movie has to be honored as well. Here are the best and most style-changing outfits worn by the cast of the best Woody Allen movies.

Annie Hall

Diane Keaton

This movie marked the moment where it was okay for a woman to wear a tuxedo suit. Annie Hall, with her independence and alluring persona took that tie from her “Grammy Hall.” This is a statement we all should learn from, always take clothing from you grandmother because it will turn vintage and dramatically be cool one day.

Annie Hall

In addition to Annie’s menswear look, Woody Allen, in the movie, Alvy Singer showcases that all white is acceptable after Labor day or anytime for that matter. Just don’t spill your wine on it.


In this scene Alvy cleverly states “I feel the world is divided between the terrible and miserable…you should be glad you’re under the miserable.” Their intellectual conversation, quite fittingly matches their scholarly plaid tops, since plaid is often related to a school uniform. Case in point, next time you want to look smart grab a plaid button down.

Annie Hall-lobster

Ahhh…the lobster scene, which casually explains the two characters in the movie so vividly. In this scene Annie brings out her playful, boyish style with the accent of a scarf and a top knot bun. She made the hair style popular before it even had a name, and the scarf, well a scarf always adds definition to an outfit. Wrap it around yourself if you’re cold or rather, want to shield your neck from lobsters.




The holistically black and white film ravishes on the notion of young characters and old ideas of love. The teenage character, Tracy displays her preppy style from wearing this crisp button down and sweater-over-shoulders look. Preppy doesn’t have to be so colorful right?


If thick, shaped eyebrows ever go out of style I’m keeping the trend because Tracy looks like Cara Delevigne in this scene. And her eyebrow are ALWAYS on fleek!

Meryl and Woody

Meryl Manhattan

Meryl Part 1: Oh the young Meryl Streep (Jill in the movie) demonstrates long skirts don’t just have to be for the modest because her sassy glares convey way more than conservative. That outfit from 1979 could still be worn today, that’s when you know this outfit, and this movie for that matter, is a classic.

Meryl Manhattan gif

Meryl Part 2: This hair flip says everything about Meryl’s character, who plays Isaac’s ex-girlfriend and writes a honest, but detailed book about her relationship with him. She teaches us how to flip our hair and express, “I don’t care what you think because I’m flawless.”


With the gang together deep in discussion, Diane Keaton is the one who stands out the most. The 80’s shoulder pads and 80’s glasses looks like a go-to outfit from the designer, Yves Saint Laurent. Decades don’t go out of style guys.


Well, there you have it folks, Woody Allen is not only the master of movies, but the master of fashion as well. If you’re ever looking for more fashion inspiration aside from these two notoriously existential movies, watch all of the infinite movies made by the movie legend. I plan to continue this old movie marathon during my next break.

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