Elle Woods, Cher Horowitz, and More Fashion Icon Halloween Costumes You Can Rewear IRL

From Penny Lane to Annie Hall, there's a fashion icon waiting for you!

By Jake Thompson Oct 16, 2019 6:39 PMTags
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Halloween is two weeks away, but for most of us social butterflies, parties start THIS weekend. It's OK, breathe. Whether you're going the sexy route or couples avenue, we've got you covered. However, although costumes-from-a-bag may be convenient and time-sensitive, sometimes your costume goddess calling card is yearning to be something more classic, timeless, and above of: iconic. We're talking leading ladies from some of the most quote-worthy and renowned films of all time and how to style them IRL!

Whether you want to test out your Legally Blonde jargon as pretty-in-pink Elle Woods, or debate your way through tartan plaid as everybody's favorite Clueless teen queen Cher Horowitz, we're here for you, fashionistas. We've handpicked costume profiles for some of the most iconic women in cinema—from Sex and the City's Carrie Bradshaw to Almost Famous' Penny Lane—so all you have to do is click the checkout button and prepare yourself for rounds of compliments on your costume. 

Our only question: Which leading lady will you be?

14 Genius Couples Costume Ideas for Halloween 2021

Get Elle Woods' Look: Think pink! Find a tailored blazer and structured skirt in Elle's signature Pantone to pull off this character costume. Add a pill box hat and a blingy stiletto and you're ready to apply to Harvard, pals.

SHEIN Solid Button Breasted Blazer & Wrap Skirt Set

Flirty meets fun with this executive two piece set in sugar pink. 

Pillbox Hat

Top off your look for the frightful night with a '50s pillbox hat that's cute to boot!

Jewel Badgley Mischka Darlene Embellished Ankle Strap Sandal

Ice your ankles out with these blingy stilettos that will take your costume to new blonde heights.

Get Cher Horowitz's Look: Think yellow tartan plaid all over! Find a fitted blazer in the yellow textile print and a matching skirt to kick off this costume. Add some sassy knee highs and you'll be the class president with a heart of gold before you know it.

Tall Checked Blazer

Fancy meets free-spirited in this structured blazer in yellow tartan plaid. 

Woven Belted Zip Front Check Mini Skirt

Put some flair into your fright with this matching tartan plaid skirt that will really sell your look.

Over The Knee Socks

You'll be the smartest in the classroom with these chic knee high socks.

Get Mia Wallace's Look: For the Pulp Fiction fashionista, think oversized men's dress shirt, some black dress slacks, and a blunt black bob. If you're feeling festive and want to make it uncanny, add a cigarette. 

H&M Slim Fit Easy-Iron Shirt

An oversized men's dress shirt will be the envy of the group for its functionality and comfort.

Women's Skinny Ankle Pant

Find a pair of dress slacks that you can dance, move, and shake all night in!

Costume Bob Wig

Finding a razor sharp black bob will transform this costume into overdrive.

Get Bad Sandy's Look: For the Grease go-getter, think off-the-shoulder halters, faux leather leggings, and a curly blonde mane. If you are feeling especially spooky, add a red lip and a cigarette to be the baddest. 

H&M Short Off-The-Shoulder Top

Keep it flirty and fun with this off-the-shoulder halter top.

Faux Leather Leggings Pants

Sassy meets sexy with these faux leather leggings. 

The Bad Girl Wig

Be the baddest on the block and complete your costume with this curly blonde wig. 

Get Mrs. Robinson's Look: To be The Graduate's original cougar, think oversized leopard faux fur coat, an auburn side bob, and a dreamy pink lipstick. 

BCBGeneration Leopard Print Faux Fur Zip Jacket

Take a walk on the wild side with this one-of-a-kind leopard print faux fur jacket. 

Short Brown Wig

Stylish and chic, this auburn side bob will elevate this costume to uncanny proportions.

MAC Velvet Teddy Lipstick

Channel your inner princess with this creamy babydoll pink rouge that's perfect for your lippy demise. 

Get Annie Hall's Look: Think men's oversized dress shirt, vest, a slouchy pant in taupe or tan, and a wide brim floppy black hat. If you're feeling extra (it's Halloween! Why not?) add a bowtie to complete the look.

H&M Suit Vest

Cut shapes in this fitted men's vest to show off your feminine silhouette. 

H&M Wide-Leg Pants

These wide-leg pants will up your costume's cool factor and can double as office wear for the rest of the year!

Women's Wide Brim Floppy Hat

You'll be the talk of the town with this quirky bowler hat.

Get Penny Lane's look: Think '70s coat, bell bottoms, and some psychedelic shades to get Penny's iconic look. If you're not lucky enough to have a wavy mane, you'll want to find a wig to match the era.

Show Me Your Mumu Coat

Be the disco diva you were born to be in this '70s inspired jacket.

H&M Mini Flare High Jeans

Add some literal flair to your costume with these high waisted flare jeans.

‘70s Round Sunglasses

You'll be the grooviest ghoul at the ball with these psychedelic shades.

Get Carrie Bradshaw's look: Think pink tank, giant white tulle skirt, and some strappy stilettos to get the city slicking character's iconic look. 

H&M Short Jersey Top

Take NYC by storm in this cute jersey tank in salmon.

Knee Length Tulle Skirt

We couldn't help but wonder: this tulle skirt is TV perfection.

Steve Madden Sane Ankle Strap Sandal

Stop traffic (and hail a cab) in these shiny stiletto winners.

Get Holly Golighty's look: If you want to enjoy Breakfast at Tiffany's, think LBD, some classy pearls, and an even classier tiara to take on this timeless costume. When in doubt: grab four of your girlfriends and be everybody's favorite moms from Monterey, the Big Little Lies crew. 

Little Black Dress

Formal meets functional in this classic LBD.

Pearl Long Necklace

Add a little drip for your neck with this pearly delight.

Crystal Tiara Crown

Own your queendom in this gold rose tiara and earring set.

Check out these last-minute costumes and find out the best places to buy Halloween candy in bulk on Today.