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All-Time Greatest: How we chose the most stylish movies and TV shows

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Image Credit: Everett Collection

In the fashion world, they says what goes around comes around. So when we compiled our lists of the top 20 most stylish movies and TV shows, we couldn’t include fashion juggernauts like Sex and the City without also paying homage to classic wardrobes like the 1970s working-girl style of Mary Tyler Moore.

Naturally, the process began with a list… a very long list. After poring over still photos and fashion news coverage, we identified the titles that have had major moments in fashion, received recognition in the form of Emmy and Oscar nominations and wins for costume design, and made an impact on pop culture.

Many of the titles that made the final cut include characters who became style icons, and often, the actors who played them helped set real-world trends too.

Alongside Sarah Jessica Parker (SATC‘s Carrie Bradshaw) and Kerry Washington (Scandal‘s Olivia Pope) are perennials like Marilyn Monroe, Audrey Hepburn, and Grace Kelly.

We have Breakfast at Tiffany’s to thank for the little black dress, but it was the impossibly chic Hubert de Givenchy gowns  — curated by costume designer Edith Head  — that inspired us to put Hepburn’s Funny Face in the number four spot.

As for Monroe, both How To Marry a Millionaire and Gentleman Prefer Blondes made the short list, but the bombshell’s figure-hugging gowns juxtaposed against Tony Curtis and Jack Lemmon’s cross-dressing costume scenes cinched the number seven spot for Some Like It Hot.

Other films we considered included Chicago, Pretty Woman — sure, she’s a prostitute, but how many times have you seen that Rodeo Drive fashion montage? — Moulin Rouge, Rebel Without A Cause, Bullitt, and All About Eve.

As for the small screen, Laverne & Shirley, Suits, and Designing Women all made the short list, but when we asked which shows had inspired trends or caused a fashion sensation, the top 20 were revealed. Thanks in part to Miami Vice, loafers (sans socks) and a muted rainbow of pastel suits and shirts were de rigueur in the 1980s. My So-Called Life did almost as much for flannel shirts as Kurt Cobain. Sex & The City put Manolo Blahnik on the map. Mad Men brought back 60’s style in the form of a clothing collection from Banana Republic. Fans took to Twitter to ask ‘What is she wearing?!’ as they watched the designer fashion parade on each episode of Gossip Girl.

Some of our picks were of-the-moment, others were a blast from the past, but they all capture the fashion zeitgeist of their time.

Still, we’re willing to admit that style is subjective. Was there a movie or TV show that should have made our list but didn’t? Do you disagree with any of our choices? Head down to the comments section and tell us what you think.


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