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Hollywood's Most Iconic Looks

Award season is in full force. If actions speak louder than words, then a hand-sewn bubblegum-pink prom dress (ah, Pretty in Pink) absolutely screams. In honor of movie awards season, we’ve compiled our 15 favorite cinematic styles, as memorable as the films and actors themselves.

Ingrid Bergman’s Menswear Separates in Casablanca

Sure, Katharine Hepburn made pants a stylish option for women in The Philadelphia Story, but it was Ingrid Bergman and costume designer Orry-Kelly who solidified the trend in Casablanca. Besides the menswear-inspired trench coats, perhaps the most iconic look in the film is that wide-brimmed hat (tilted to the side, of course). Here’s lookin’ at you, kid.

Grace Kelly’s Silk Nightgown in Rear Window

This scene alone is responsible for our love of white clothing in general. Oh, and slip dresses. Oh, and fancy pajamas. Costume designer Edith Head really hit the nail on the, er, head.

Tippi Hedren’s Green Suit in The Birds

When you need to look away from those scary-as-anything birds (seriously, what gives?), you should just focus on Tippi’s sharp green suit.

Anne Bancroft’s Leopard Coat in The Graduate

Ava Gardner famously missed out on playing the role of The Graduate’s married temptress, yet it’s almost impossible to imagine anyone other than Anne Bancroft starring in the legendary spot. Her leopard coat is everything. Bancroft walks into the bar, sits down and ever so slightly drapes the fur off her shoulders. You’ve seduced us, Mrs. Robinson.

Barbra Streisand’s Nails in The Way We Were

There’s a lot of stroking Hubbell’s face in this movie, so it’s only natural that you get a lot of face time with Katie’s nails. And they’re not just any ol’ nails. Katie’s long, pointed, red-manicured talons have inspired us (and Rihanna) ever since.

Diane Keaton’s Ties in Annie Hall

Based on Keaton’s real-life style, the titular character in Annie Hall has one of the most recognizable movie looks of all time. From loose khakis to ties and hats, it’s a style that has been continuously referenced by designers in their “borrowed from the boys” menswear-inspired collections.

Olivia Newton-John’s Leather Jacket in Grease

Black leather and red pumps are the perfect signal that Sandy had transformed from bookworm to bombshell. Fun fact: She had to be sewn into that outfit during shooting...it was that tight. Tell me about it, stud.

Molly Ringwald’s Prom Dress in Pretty in Pink

While we snicker at most red-carpet gowns that resemble what we wore to our prom, Andie Walsh’s ’80s-tastic frock holds a special place in our heart. After all, she made it herself! Teens everywhere followed suit and began to “sketch” their own prom dresses.

Jennifer Grey’s Denim Shorts in Dirty Dancing

We don’t have the thighs to pull off the “jeans or shorts?” look. But if we did, trust us, we would.

Julia Roberts’s Strapless Dress in Mystic Pizza

It would be too easy to say Julia in Pretty Woman (although it was obviously the first thing that came to mind). But no, the best Julia was Ms. Roberts rocking a huge bow on her date with the boy from the rich side of town.

Matthew McConaughey’s Ted Nugent T-Shirt in Dazed and Confused

Alright, alright, alright. There are plenty of men in film who are probably more qualified to grace this list (James Dean, Kevin Bacon, all James Bonds ever). But a man in a suit always looks good. However, few can rock peach-colored flares and a band tee quite like David Wooderson.

Liv Tyler’s Kilt Skirt in Empire Records

And cropped mohair sweater. And combat boots. Costume designer Susan Lyall admits to scoring the fluffy blue top and plaid skirt at Patricia Field or Canal Jeans, or something like that. And it turns out the boots were Tyler’s own. We have a friend who hasn’t stopped wearing this ensemble since.

Gwyneth Paltrow’s Polo in The Royal Tenenbaums

A preppy Lacoste polo, a glam fur and a sharp Anna Wintour-esque ’do make for the perfectly weird movie look. Add liberal amounts of eyeliner and copious cigarettes and you’ve got the fantastically moody and broody Margot Tenenbaum, an icon of emo stoicism.

Lucy Liu’s Kimono in Kill Bill: Vol. 1

Not exactly an outfit we’re dying to don, but O-Ren Ishii’s all-white kimono is no doubt iconic. In fact, Liu claimed it was the toughest part about her role. They had to fly someone in from Japan to put it on properly, and it was so tight that she couldn’t move her knees in the fight scenes.

Keira Knightley’s Green Dress in Atonement

The bias-cut green dress could be considered the third character in the film’s decisive library scene. The dress was made by costume designer Jacqueline Durran, and the emerald-green color was specifically chosen to represent temptation and to coincide with excerpts from the novel. Later in the plot it turns out that dress had something to do with the bombing of London. It was that powerful.