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76 Most Stylish Movies Featuring Iconic And Timeless Fashion Looks
Movies & tvJAN 12, 2023

76 Most Stylish Movies Featuring Iconic And Timeless Fashion Looks

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The worlds of fashion and film are closely entwined and often influence one another. Film costume designers frequently draw ideas from fashion designers to translate iconic runway looks to the big screen, while clothes worn in movies affect what is deemed fashionable at the time of the film's release. When it comes to judging the most stylish movie characters or fashion in movies in general, the assessment may be very much subjective. Yet, many iconic outfits from movies gained their title by establishing what is deemed 'classic' fashion looks even by today's standards.
The most stylish movies, the fashion trendsetters of the time, rose with the earliest Hollywood films. Numerous classic films are to blame (and thank) for the timeless fashion fads still 'hot' today. Arguably some of the most stylish movies of all time were released during the golden age of Hollywood. Marlon Brando's black leather jacket over a white tee look in The Wild One (1953), Audrey Hepburn's little black Givenchy dress in Breakfast At Tiffany's (1961), or Marilyn Monroe's iconic white dress in The Seven Year Itch (1955) are just some of the famous movie outfits that grew to become some of the most iconic movie costumes.
Below, we've assembled, in our opinion, the most stylish movies, ranging from old Hollywood classics to modern-day blockbusters. Make sure to upvote the films you would like to see higher up on the list and rearrange the rankings to your liking! Also, did any iconic character outfits from the movies below stick out to you? Did we leave out any other films deserving a spot on the list? Let us know!

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#21 Kingsman: The Secret Service

Merlin, Harry and Gary looking at something
13points

#22 Pretty In Pink

Andy and Duckie having a conversation
13points

#23 La Haine

Vinz and Skinhead standing on the balcony
Rather than the aesthetic appeal of Paris, the black-and-white movie La Haine emphasized the underclass of society. The protagonists are a racially varied bunch of young people stuck in the Parisian economic and social underclass. You'll notice all the major labels, like Nike, Carhartt, Everlast, Reebok, Lacoste, and plenty of sportswear, as they are all infatuated with American hip-hop culture.
12points

#24 Grease

Film shots from the movie Grease
12points

#25 Romeo + Juliet

Romeo crying
12points

#26 Cruella

Cruella wearing black dress
11points

#27 On The Waterfront

Film shot from the movie On The Waterfront
If you searched the dictionary for "Cool Guy," you may come across a photo of Marlon Brando from the 1950s. Okay, you won’t, but you get what we are trying to say. The man was so cool that he essentially made the white T-shirt popular. And that says a lot. To rock that "Marlon Brando look," you only needed to put on a white T-shirt and a black jacket and pull your hair back slightly. The key takeaway is that Brando made simple, effortless, and minimal appear great.
10points

#28 The Thomas Crown Affair (1968)

Vicki and Thomas lying on the beach chairs
10points

#29 Fight Club

Tyler and Narrator talking
10points

#30 Black Panther

Film shot from the movie Black Panther
10points

#31 La Dolce Vita

Film shot from the movie La Dolce Vita
While Anita Ekberg's portrayal of Sylvia in that long black dress at the Trevi Fountain may be the film's most recognizable scene, it was Marcello Mastroianni's outfits that we feel earned the film the 1961 Academy Award for Best Costumes. Arguably no other character in any other movie contributed to popularizing the traditional Italian look for men — slim-fit suits, double-cuffed shirts, and big, bold cufflinks — more than Mastroianni.
9points

#32 American Gigolo

Julian wearing sunglasses
9points

#33 Bonnie And Clyde

Film shot from the movie Bonnie And Clyde
9points

#34 Breathless

Film shot from the movie Breathless
It's safe to assume that the young director had no idea how his movie would affect the clothing choices of countless young Americans leaving for a semester abroad in Paris. Jean-Paul Belmondo and Jean Seberg look effortlessly and naturally at ease in their outfits, as if they simply wore whatever they brought to work each day. Actually, there is no mention of a costume designer in the credits. Thus, given the creative leeway Godard was well-known for granting his actors, it's possible that they were able to choose many of their outfits on their own.
9points

#35 The Thomas Crown Affair (1999)

Film shot from the movie The Thomas Crown Affair
8points

#36 The Royal Tenenbaums

Film shot from the movie The Royal Tenenbaums
8points

#37 Annie Hall

Film shot from the movie Annie Hall
8points

#38 The Philadelphia Story

Tracy raising a glass
8points

#39 The Man from U.N.C.L.E.

Film shot from the movie The Man from U.N.C.L.E.
7points

#40 The Danish Girl

Lili reading a book on the couch
7points
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