Glamorous Halloween Costumes Inspired By Old Hollywood

Designed by Richard Chance
So far, 2017 has been quite a trip. It's hard not to be affected by the daily tumult. So, seize your opportunity to indulge in some escapist fare on Halloween. For the duration of Halloween weekend, you can pretend you're from another era. That sounds nice, right?
With their updos and gowns, the women of Old Hollywood personified glamour. Of course, the images of Old Hollywood that most immediately come to mind are Audrey Hepburn in Breakfast at Tiffany's, looking mischievous in a black dress and pearls, or Marilyn Monroe swirling around in a white halter dress. But your options don't end with Audrey and Marilyn, even if all the Halloween parties you've been to may have implied otherwise. From Katharine Hepburn to Josephine Baker, style icons of the past can inspire you to build a unique Halloween costume.
Get out your flare pants, your fedora hats, and your elbow gloves. These classic looks will provide your next costume inspiration.
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Audrey Hepburn as Princess Ann from Roman Holiday

In Roman Holiday, Hepburn's character escapes from the confines of royalty, gives herself a haircut, and has a rollicking good time among the people.

Copying the look is pretty simple. Ann walks around Rome wearing a white button-down shirt, tucked into a long pink circle skirt. She ties a tiny scarf around her neck. In addition to the outfit, you'll have to copy Ann's hair. Either braid your hair into an updo, or just wear a high ponytail.
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Petition to bring back the mini scarf.
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Rosalind Russell as Hildy Johnson in His Girl Friday (1940)

Russell's character is a journalist who makes pinstripes chic.
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Joan Crawford as Mildred Pierce from Mildred Pierce

Mildred Pierce is an overextended, exasperated mother, who manages to still look fabulous and walk around in luxurious coats. To be Mildred, wear a long white dress with some classic Crawford shoulder pads. Then, drape yourself with a (faux) fur coat. Now you're ready to do whatever it takes to deal with your evil daughter.
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Bette Davis as Jane Hudson in What Ever Happened to Baby Jane?

This is your opportunity to color outside of the lines, especially while applying lipstick. Earlier this year, Ryan Murphy dedicated an entire miniseries to the filming of What Ever Happened to Baby Jane, called Feud. Susan Sarandon played Bette Davis playing Jane Hudson (got that straight?).

Before getting into the makeup, buy a vintage-looking white dress with a pink sash, and a blond curly wig. Then, the fun part. Give yourself a hefty layer of white face paint, then two strong dollops of blush. Wear sloppy black eyeliner, and lots of eyelashes. Finally, go wild with the red lipstick.

If you're really committed, decorate a doll just to look like Baby Jane, and carry it around.
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Need inspiration for Baby Jane? Scarlet Johansson did an intimidatingly accurate impression of the film character.
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Josephine Baker as herself

When you think of the Jazz Age, you think of Josephine Baker, a famous performer and entertainer best known for headlining the Folies Bergère in France. Begin your costume with a champagne-colored gown — satin, if you can. Wear large, dangling rhinestone earrings, and an equally sparkly head band that lies flat on your forehead. In terms of makeup, wear burgundy lips, and very heavy gray eyeshadow. To copy the look of the times, make your eyebrows appear to be thinner than they are.

To distinguish yourself from other figures of the Jazz Age, carry around a stuffed cheetah — Baker had a pet cheetah named Chiquita.
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Tyra Banks once appeared on an episode of Gossip Girl dressed as Baker.
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Audrey Hepburn as Holly Golightly from Breakfast at Tiffany's
Option 1

Let's be real: When you think of Old Hollywood glamour, you think of Audrey Hepburn wearing a tiara in a little black dress. Images of her performance as Holly Golightly have adorned many a dorm room and inspired many a Halloween costume.

For the costume, you'll need a black sleeveless dress, a pearl strand necklace, black kitten heels, a tiara, rhinestone earrings, and giant black sunglasses.
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Unsurprisingly, this iconic image of Audrey Hepburn is a very popular Halloween option.
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Audrey Hepburn as Holly Golightly from Breakfast at Tiffany's
Option 2

At some point in the movie, Holly's partying habit catches up to her. She stumbles around in a an oversized white shirt, tassel earrings, and a teal bedazzled sleep mask.
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Dorothy Dandridge as Carmen Jones in Carmen Jones

If you're pressed for time, then turn to this step-by-step guide to creating a Carmen Jones costume. Likely, you'll find almost all the ingredients necessary in your closet, aside from the retro wig. The article's author wore a black, off-the-shoulder shirt and a long red pencil skirt, then carried around a fake rose. Pretty simple.
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She absolutely embodied Dorothy Dandridge's look in Carmen Jones.
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Marilyn Monroe as the Girl from The Seven Year Itch

You'll have to break the rule of not wearing white past Labor Day to pull off this iconic look. Unlike other costumes on this list, which require some closet-digging and creative thinking, this costume can be bought. If possible, cart around a portable fan.
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Warner Bros/Kobal/REX/Shutterstock
Ingrid Bergman as Ilsa Lund from Casablanca

You simply can't find suits like Ilsa's nowadays. The hat, however, is readily available. To be Ilsa at the moments of her departure from Casablanca, wear a brown jacket and long, brown pants or skirt. Carry around a briefcase. Look forlorn.
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Katharine Hepburn as Tracy Lord from The Philadelphia Story

Luckily for you, flare pants are back in, so Katharine Hepburn's look from The Philadelphia Story is easier than ever. Tuck a black sleeved shirt into long, light-hued flare pants. Wear black boots. If you're feeling ambitious, try styling your hair like Hepburn's with this tutorial.
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Ava Gardner as Kitty Collins in The Killers

To copy Gardner's dramatic look in The Killers, start with a strapless sweetheart-neck black dress, then add a dash of DIY. Sew a strip of black fabric from the center of the dress, over your left shoulder, onto the back of the dress. Then, wear strappy black heels and long black elbow gloves. This DIY video will teach you exactly how to get your hair to look like Kitty Collins.
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Sophia Loren as Yasmin Azir in Arabesque

The raw materials for this costume are incredibly simple: Pink towels. The trick is in getting them to stay on. Clasp the towel together snugly with a pin, so it doesn't fidget when you go out. You may want to wear nude tights. Then, apply a dramatic cats-eye and a nude gloss to your lips.
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Lena Horne as Fernway de la Fer in Broadway Rhythm

This incredible DIY gives step-by-step tips for creating Horne's bright, unforgettable outfit. For materials, all you need is a fuschia maxi skirt, a yellow crop top, hoop earrings, and faux yellow flowers to put in your hair. Then, the DIY instruction guide will lay out exactly how to alter the skirt and shirt to emulate Horne's look.
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Lana Turner as Cora Smith from The Postman Always Rings Twice

Bring back your clothes from the summer. Wear white high-waisted shorts with a white crop-top, preferably one that can be tied in the middle. You'll need white heels or flats as well. Finally, tie your hair back in a white turbie twist.
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Audrey Hepburn as Jo Stockton from Funny Face

If you live in New York, it's likely you have this costume sitting in your closet already. You'll need black jeans or pants, black shoes, and a black long-sleeved shirt. Tie your hair back into a bun, and walk around like you're a bookstore owner who disdains the fashion industry, as Hepburn's character in the movie does.
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