The Most Fashionable Movies of All Time

I previously posted about TV shows you should binge watch right now so I thought I would continue with the most fashionable movies ever made. I’m hoping you follow me because you love fashion and outfit inspiration if you do then this is a list of movies for you.

There are countless movies out there that have incredible fashion moments and truly capture the essence of the movie, but to me, these are some of the most iconic and drool-worthy looks cinema as ever seen.

As a self-proclaimed fashion obsessor, there are moments in movies that have stood the test of time to me and I can even remember being mesmerized as a child by a certain dress or an actress that was the epitome of chic.

I’ve included everything from as recent as 2018 with Crazy Rich Asians to as far back as 1937 with the Awful Truth. If you’re not only looking for new movies to pass the time, but longing to feel inspired by fashion then check out my list of the most fashionable movies of all time.

THE MOST FASHIONABLE MOVIES EVER

A Single Man (2009)

Two words: Tom Ford…enough said.

All About Eve (1950)

This movie is a perfect example of how fashion in movies can be more than just a pretty outfit. It tells a much greater story. You’ll swoon over Betty’s Davis’ old Hollywood fashion.

Atonement (2007)

13 years later and we still cannot forget that bright green silk dress worn by Keira Knightly!

Breakfast at Tiffany’s (1961)

Holly Golightly may be one of the most fashionable women cinema has ever seen. Hands down!

Clueless (1995)

If you didn’t grow up watching and trying to emulate Cher Horowitz’s looks who are you? It’s 90’fashion at its best.

Crazy Rich Asians (2018)

A movie about some of the wealthiest and elite in the world so you have to believe the fashion is up to par.

Dial M for Murder (1954)

Another Hitchcock film where the fashion is as dramatic as the movie. Grace Kelly’s classic head-to-toe red lace look is EVERYTHING.

Gilda (1946)

Reportedly, more than $50,000 was allocated for Hayworth’s wardrobe for this film and this was 1946.

Gone With the Wind (1939)

The iconic green velvet dress worn by Vivienne Leigh still gets me to this day

Funny Girl (1968)

Follows Barbra Streisand’s characters from vaudeville to Broadway so expect dramatic costumes of fur, rhinestones, and jewels to match.

High Society (1956)

Grace Kelly’s costumes are nothing but classic and breathtaking in this movie. Her embellished tulle dress is to die for.

How to Marry a Millionaire (1953)

The perfect depiction of classic 1950’s fashion – full skirts, fitted waists,  cat-eye glasses, and ruby red lips.

Legally Blonde (2001)

Elle Woods never disappointed in her all pink ensembles from college student to Harvard law student

Marie Antoinette (2006)

Think elaborate haute couture just like the infamous and indulgent Queen the movie is about

Mean Girls (2003)

A movie that shaped my early teen’s fashion because at that time who didn’t want to dress like the plastics?! Think lots of pink, leather, and plaid.

North by Northwest (1959)

Think elegant late 50’s looks with pops of red, beautiful full skirts, and always a touch of femininity bought straight from Bergdorf Goodman.

Pillow Talk (1959)

Doris Day’s fashion-forward hats and elegant cocktail dresses are still incredibly stylish today.

Pretty Woman (1990)

Every outfit Julia’s Robert’s wears post-makeover from hooker to classy woman are iconic

Rear Window (1954)

Grace Kelly’s costumes steal the show in this Hitchcock thriller.  Her infamous off the shoulder tulle dress with an embellished floral pattern is enduringly chic.

Roman Holiday (1953)

Audrey Hepburn was the epitome of chic in the ’50s and ’60s and her style as the runaway princess in hiding is drool-worthy.

Sabrina (1954)

Fashion in the 1950s was elegant, classic, and always chic. Sabrina delivers all of that and more! Plus Audrey was dressed exclusively by Givenchy, which started her long love affair with the brand.

The Awful Truth (1937)

The glamor of the socialite 1930s fashion is evident in this classic. Plus, the infamous Edith Head is the costume designer and she always gets it right.

The Devil Wears Prada (2006)

A movie all about the fashion industry and meant to take place at Vogue so yeah the fashion is pretty amazing in this movie. I would still wear many of the outfits today almost 15 years later.

The Great Gatsby (2013)

The ultimate 1920’s glamour. Need I say more?

The Philadelphia Story (1940)

The fashion from this movie was just at the turn of a new decade so there is still a lot of 30’s inspiration. Think of Hepburn’s classic shirts and slacks, sophisticated gowns, and even an all-white dressing gown that will leave you speechless.

Titanic (1997)

The decadence of the famous ocean liner calls for decedent costumes to match. Kate Winslet’s turn of the century fashion will forever be iconic in cinema fashion history.

What A Girl Wants (2003)

You may not instantly think of fashion when it comes to this movie, but that stunning periwinkle silk dress Amanda Bynes wears at the ball is still stylish today.

What are other movies do you love or think are the most fashionable movies of all time? Share your thoughts in the comment section below! I was inspired by Glam Life Living for this blosg post.