When you think of Audrey Hepburn, Marilyn Monroe, James Dean, what comes to mind? Icons. Film. Fashion. All of these actors hit their movie sets and made a kick-ass outfit famous. With the best wardrobe stylist backing up our talents it still takes something spectacular to make an outfit an icon. With Sex and the City 2, a film that is more about what they’re wearing than what’s going on in the film, hitting theaters on Thursday, May 27, 2010, we thought we’d put a list together of the Top 10 Most Fashionable Characters of All Time!

Take a look…

10. Andie Walsh in Pretty in Pink

For all you nerdy girls out there who were scared to death of going to prom but decided to go and make a statement with your own prom dress, Andie Walsh is your god! She made stapling together miss-matched fabric “cool.” Never before was dirt poor and from the wrong side of the tracks as stylish as in the 1986 film Pretty in Pink. She made vintage the it thing for teenage girls everywhere.

Played by: Molly Ringwald
Signature Look(s): Pink prom dress, florals, vintage clothing
Era of Impact: The mid-80s
Influence in fashion: Always remembered when looking through old photos of your prom or after you get dumped! Odd… but true!

9. Cher Horowitz in Clueless

Cher Horowitz became a hero to Catholic school girls everywhere when she made plaid skirts and knee socks fashion-friendly in 1995′s Clueless. She showed us that the same flannel and checkered material used to keep you in line could actually make you stand out — but in a good way.

Played by: Alicia Silverstone
Signature Look(s): Over-the-knee socks, tartan suits, berets, dolly shoes
Era of Impact: The mid-90s
Influence in fashion: Mainly only through the 90′s but still remembered (and possibly even feared)

8. Bonnie Parker in Bonnie and Clyde

Faye Dunaway revolutionized what a villain could look like when she appeared in 1967‘s Bonnie & Clyde. She proved that just because you do bad things it doesn’t mean you have to wear bad clothes. Bonnie Parker was living in the south during the harsh “Great Depression,” but she didn’t let the time or place dictate her style.

Played by: Faye Dunaway
Signature Look(s): Pencil skirts, berets, moll hats, blonde bob cut,
Era of Impact: The 1930s, late-60s and 70s
Influence in fashion: Remembered, revived at times, always loved.

7. The Girl in The Seven Year Itch

There’s no denying that Marilyn Monroe was a glamour goddess during the 50s, but when she appeared as “The Girl” in The Seven Year Itch, she became pure sex! She proved that wearing all white shouldn’t be reserved for your wedding day and can be just as scandalous as any of the colors in the rainbow.

Played by: Marilyn Monroe
Signature Look(s): Iconic white dress, plunging neckline
Era of Impact: The mid-50s and 60s
Influence in Fashion: What human doesn’t think of this when they walk over a vent? TIMELESS!

6. Susan in Desperately Seeking Susan

What wouldn’t Madonna do? Something to think about when accessorizing. She turned underwear into daywear with gloves and and a lot of red lipstick. In 1985, “Like a Virgin” was topping the charts, and Madonna’s super 80s look in Desperately Seeking Susan was on high-demand. Susan gave women the courage to dress in ways they would be embarrassed about for decades to come!

Played by: Madonna
Signature Look(s): Headbands, leggings, studded boots, jackets, red lips, big hair-dos, lacy cropped tops
Era of Impact: The 80s and late 2000s
Influence in Fashion: Huge in the 80′s then back this decade, maybe it’s an every couple of decade thing? God help us… and don’t throw out those leggings, they’ll be back!

5. Roger Thornhill in North by Northwest

When Cary Grant starred in North by Northwest as Roger Thornhill, danger never looked so good. He wore one outfit through the entire film, a gray tailored suit that survived a kidnapping, a car accident, a shooting, and most importantly his sex appeal.

Played by: Cary Grant
Signature Look(s): Tailored-gray-ventless-three-button suit
Era of Impact: The 60s
Influence in fashion: Class never goes out of fashion… and don’t think all the Mad Men cast aren’t looking to Grant as their role model.

4. Annie Hall in Annie Hall

Before Avril Lavigne, Joan Jett, and that badass chick from “The L Word,” Diane Keaton‘s alter ego Annie Hall blazed the trail as a gender bending woman in the 1970′s. Before she came along, a female wearing trousers and a tie would have been cited as “questionable” but nowadays it’s considered “chic.”

Played by: Diane Keaton
Signature Look(s): Male wardrobe on a woman, ties, vests, long skirts, boots
Era of Impact: The late-70s
Influence in fashion: We all loved it, but didn’t necessarily mind letting it go. Although the pieces of it, either the tie, the pants, or the vest randomly come back into fashion and remind us of good ol’ Annie.

3. Carrie Bradshaw in Sex and the City

Carrie Bradshaw gets away with anything and everything. Fake gold – check. Mixing high-end designers with vintage – check. Obvious product placement – check. You name it, she’s done it. Bradshaw and her 3 slutty friends single handedly introduced designer Manolo Blahnik and his overpriced stilettos to the rest of the general population.

Played by: Sarah Jessica ParkerSignature Look: Nameplate necklace, Manolo Blahnik’s and other expensive footwear, vintage clothing
Era of Impact: The Late-90s and early 2000s
Influence in fashion: Well she INSPIRED the list that’s gotta count for something!

2. Jim Stark in Rebel Without A Cause

When you think of 1950′s teen angst one name comes to mind, James Dean. You can’t imagine the actor without the red motorcycle jacket, tight jeans and that white T-shirt he wore as Jim Stark in 1955′s Rebel Without A Cause. The character’s style has been copied countless times over the past 50 years, even Robert Pattinson admitted that Stark’s cool demeanor was his inspiration for Twilight‘s Edward Cullen (shutter).

Played by: James Dean
Signature Look(s): Red leather jacket, white t-shirt, denim
Era of Impact: The mid-50s and 60s
Influence in fashion: Really, this could be #1. Classic, loved, revered, tell me what actor walking around LA wearing a leather jacket doesn’t try to look like James Dean? He makes me want to smoke a cigarette just so I can be like him.

1. Holly Golightly in Breakfast at Tiffany’s

There’s a point in every girl’s life when she scrounges through her mother’s closet in a faint attempt to dress up like Holly Golightly from Breakfast at Tiffany’s. The image of Audrey Hepburn in that little black dress, with those chunky pearls, and thick sunglasses is the epitome of class. Golightly makes the top of our list because she’s been often imitated but NEVER duplicated.

Played by: Audrey Hepburn
Signature Look(s): The little black dress, pearl necklace, cigarette holder
Era of Impact: The 60s
Influence in fashion: Timeless. Iconic. Perfection. Has lasted since the 60′s and is still gorgeous! Whoever knew that a little black dress and some big glasses could change the world?!

Who do you think should have been on our list?