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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!

#1 Funny Face

Funny Face
Funny Face officialized Hepburn's partnership with French fashion designer Hubert de Givenchy. The actress initially got in touch with the designer to create outfits for her role in Sabrina (1954), but too pressured for time, he let her choose from his collections instead. After Sabrina won the Oscar for Best Costume Design, Hepburn asked that Givenchy make all of her screen appearances from then on, starting with Funny Face. The result was a wardrobe that, almost 70 years later, is still a reference point for fashion today.
33points

#2 North By Northwest

North By Northwest
Alfred Hitchcock recognized the importance of clothing, a significant component of several of his masterpieces. The blue/gray glen check suit with three buttons, no vents, and inward pleats and cuffs that Cary Grant wore in the suspenseful Alfred Hitchcock film is perhaps the most well-known suit in movie history. Eva Marie Saint, quoted in the book Cary Grant: A Celebration of Way, said, “Hitchcock made everybody in the picture dress in a classic style… He didn’t want the picture to date because of the clothes.” 
30points

#3 Breakfast At Tiffany's

Breakfast At Tiffany's
29points

#4 Quadrophenia

Quadrophenia
Quadrophenia fashion endured even after its premiere more than 40 years ago. Mod fashion is still prevalent on high streets today as the preferred attire of the fashionable elite, whether it be nostalgic Mods or younger generations influenced by this cult masterpiece. Yet, Mod style wasn't about labels; it was about having "the look" and identifying with the Mod way of living. As part of its stylistic aesthetic, the movie features traditional Italian-cut suits, penny loafers, desert boots, and fishtail parkas.
28points

#5 The Grand Budapest Hotel

The Grand Budapest Hotel
Wes Anderson’s Oscar-winning film has maintained Anderson’s signature aesthetic of beautiful pastel colors, intricately detailed sets, and characters on the verge of insanity. But what really catches the eyes are the costumes. Italian costume designer who worked on the film, Milena Canonero, picked the style and cut of the hotel uniforms that are true to the 1930s. Color-wise, The Grand Budapest Hotel is a very aesthetically pleasing cinema production.
28points

#6 Clueless

Clueless
The outfits Cher wore in the film, including her notorious yellow plaid suit and strappy red slip dress, epitomized peak ’90s fashion. After its premiere in 1995, Clueless bred a fashion legacy that influenced trends for many years. In fact, the ensembles worn in the movie, designed by Mona May, went beyond the bounds of 1990s fashion and continue to impact trends of today.
26points

#7 Trainspotting

Trainspotting
Without its distinctive look, Trainspotting would not have been what it was, and Rachael Fleming, who created the costumes, was to thank. Even without the often-parodied "choose life" monologue overlay, the image of a teenage Ewan McGregor running down the street in skinny jeans, a bomber jacket, and a vintage T-shirt is quite iconic. Then, there's Kelly McDonald in the club scene. Any adolescent girl in the 1990s would have recognized her from that sequin slip dress, red coat, and strappy sandals.
25points

#8 Wall Street

Wall Street
In addition to its intriguing storyline, the 1987 movie Wall Street is also well renowned for its eccentric garments. In general, menswear in the 1980s had a slight reorientation. This may be seen in the substitution of the organic patterns of the 1970s in shirts for bold solids and stripes, in the simple lines and broader cuts of suits, and in the overall slimness of the late 1960s and early 1970s for more volume. When designing the costumes for the movie, Alan Flusser utilized current fashion trends and exaggerated them to the hilt. Interestingly, when the movie gained popularity, more men started donning fashion looks portrayed in the film. Thus, we can consider that the movie defined the Wall Street appearance more than it showed how it actually appeared in the 1980s.
24points

#9 Reservoir Dogs

Reservoir Dogs
Over the years, Quentin Tarantino has been called many things, but "fashionista" was never one of them. Yet, the remarkable director Tarantino is also praised for popularizing the fitted black suit, white shirt, and skinny black tie ensemble made famous in his 1992 film. Large pleated pants were a feature from the 1980s, yet the classic suits from the 1990s were even more oversized. Reservoir Dogs was arguably the first time men appeared in suits really fitted to them on screen. What Tarantino called his "black suits of armor" significantly influenced later film and fashion trends.
23points

#10 Singin' In The Rain

Singin' In The Rain
Although Singin' In The Rain is about the introduction of "Talkies" in Twenties Hollywood, the movie was made in the Fifties, yet the fashions reflect both. This makes it one of the most typically masculine ensembles ever seen on screen. Wide-legged wool trousers, cropped knits, thick-lapelled jackets, and great trilby hats are just a few examples of the many ‘20s allusions present in the film. Nevertheless, they are all infused with Technicolor from the 1950s.
20points

#11 My Fair Lady

My Fair Lady
In My Fair Lady, Audrey Hepburn is transformed from the mousey shop worker in a bookshop she played in Funny Face to a supermodel in Paris. Cecil Beaton's costume designs greatly enhanced the success of Lerner and Lowe's musical under the same name in New York and London. Beaton reflected on his boyhood by using the setting of 1914 to include clothing he remembered from relatives, family friends, and the gorgeous picture postcards he collected. However, the dress he created for Eliza to wear to the Embassy ball is timeless. Both the 1960s and pre-1914 can be seen in the gowns' simplicity and unadorned style.
19points

#12 Call Me By Your Name

Call Me By Your Name
The realm of striped, light blue fabrics, collared shirts, comfy shorts, and airy materials. Costume designer Giulia Piersanti is to blame for Call Me By Your Name’s flawless aesthetic. Apparently, Piersanti was quite reluctant to design clothing for the movie because the 1980s, when the story takes place, felt like an overly restrictive period. Thus, she chose vintage items that generated a sense of intimacy and timelessness, referencing old photo albums as her source of inspiration. The end result was a well-put-together selection of attire that nobly depicts the style of 1983 Lombardy.
18points

#13 Kids

Kids
Multicolored hair ties and little buns? Check. Bandanas, ringer tees, backward hats, baggy jeans, checkered shirts, and hoop earrings? Also, check. Larry Clark wanted the movie to have an authentic, documentary-style appearance. Thus, the actors, young girls and boys, wore what was appropriate at the time: cuffed Converse, low-slung denim, back-to-front baseball caps, and branded skater tees. Kids provided a different perspective during the same year teen movies like Clueless enthralled young viewers with their depictions of LA riches and high fashion. The style and mindset were unforced, true to themselves, and at ease enough to allow the kids to move about their lives carefreely.
17points

#14 The Great Gatsby (1974)

The Great Gatsby (1974)
16points

#15 Leon The Professional

Leon The Professional
16points

#16 Rear Window

Rear Window
16points

#17 The Devil Wears Prada

The Devil Wears Prada
15points

#18 Guys And Dolls

Guys And Dolls
In the film adaptation of this Broadway musical, Marlon Brando's singing may not have been up to par with that of his co-star Frank Sinatra, but his suiting was unmatched. A film about a mobster in the 1950s might be expected to contain a lot of pinstripes, padded shoulders, and black shirts worn with thin, light-colored ties. Sky's, played by Brando, eccentric choice of shirt and tie is what sets him apart from other fashion icons. He always went for dark, silky shirts in colors that matched his suit. We highly doubt he even owned a white shirt.
14points

#19 Marie Antoinette

Marie Antoinette
14points

#20 Pretty Woman

Pretty Woman
14points
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