The concept of using Halloween and costume parties as an excuse to dress a little sexy, play with gender norms, or otherwise go all out with feeling a fantasy? It’s nothing new. Fashion crowds, club kids, and celebrities have had a bit of naughty fun with the costume parties for decades. Want proof? Take a trip back in time. First, we’ve resurface W exclusive pictures of an artsy 1975 costume ball that drew the likes of Jerry Hall and Halston. Then jump a head a few years to the very NSFW Halloween bashes at the infamous Studio 54. Then, a selection of some of the best celebrity costumes from the ’70, ’80, ’90 and ’00s including Naomi Campbell, Brooke Shields, Cher, Drew Barrymore, and Chloë Sevigny. Along the way, meet plenty of drag queens, Playboy bunnies, hunky Tarzans, chic Cleopatras and plenty of other characters that are sure to rev up some inspiration for your costume this year.
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A guest in a sequined patriotic costume makes and entrance at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Arts marketing consultant Stephen Reichard and Colette arrive in a hospital bed at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Halston and his Rabbit-ettes (Nancy North, Pat Mori, and fashion illustrator Joe Eula) arrive at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Fashion designer Halston with one of his Rabbit-ettes at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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A guest in a plastic bikini and skirt makes an entrance at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Early paparazzo Ron Galella at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Model Jerry Hall in a sequined gown at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Sally Gilbert and Randolph Griffin at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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A rabbit-ette helps another partygoer adjust her costume at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests in pirate and samurai costumes at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests in metallic costumes dancing at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Nicky and Kenny Lane at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guest plays the tambourine at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guest plays the tambourine at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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New York Young actress Brooke Shields, dressed as comedian Charlie Chaplin, skates through Wednesday’s Disco as she joins others at a Halloween party here, 10/30.
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Guests in costume at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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Guests wearing harlequin masks at “Magic, Fantasy and Dreams,” a costume-ball benefit for the Skowhegan School of Painting and Sculpture.
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A man dressed in a loincloth and a woman wearing a Flamenco costume talk during the Haloween party at the nightclub Studio 54, New York City, October 31, 1981.
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31st October 1981: High-angle view of the crowd dancing at Studio 54 in New York City. Some dancers wear Halloween costumes.
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Twiggy and Tommy Tune during “My One And Only” – Closing Night Halloween Party at Mark Ballroom in New York City, New York, United States.
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A pair of clubgoers dressed as punks lie on the floor at Studio 54’s third annual Halloween party, New York, New York, October 31, 1978.
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Outside Studio 54, an unidentified would-be clubgoers arrives on a horse for the third annual Halloween party, New York, New York, October 31, 1978.
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During the third annual Halloween party at Studio 54, costumed women laugh atop the shoulders of their male companions, New York, New York, October 31, 1978.
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A pair of clubgoers dressed in Egyptian-style costumes attend the third annual Halloween party at Studio 54, New York, New York, October 31, 1978.
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A clubgoer dressed as Jesus Christ carries a large cross on the dance floor during the second annual Halloween party at Studio 54, New York, New York, October 31, 1977. The pair, who operated the Danceteria club, had been hired by new Studio 54 owner Mark Fleischman to revitalize Studio 54 after the arrest of the former owners for tax evasion.
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A couple dressed as a bride and groom at a Halloween party at Studio 54, New York, New York, October 31, 1978.
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Clubgoers inhale nitrous oxide (also known as laughing gas) on the dance floor during the first annual Halloween party at Studio 54, New York, New York, October 31, 1977. The towers could descend from the ceiling and the rise again.
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Dressed as ‘Trick or Treat,’ performance artist Annie Hickman (in a tinsel accented bikini) and a companion (covered in boxes of candy and a mask with a phallus over his nose) attend the Sex and Drugs Halloween party in SoHo, New York, New York, October 28, 1978.
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View of a nearly naked couple as they dance atop a speaker during the first Halloween party at Studio 54 , New York, New York, October 31, 1977.
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A bare-breasted lady in a peacock feather headdress dances at Studio 54’s first Halloween party, New York, New York, October 31, 1977.
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A man and woman dressed in costume dance during the ‘Magic, Fantasy and Dreams’ Halloween Eve party at the nightclub Studio 54, New York City, October 30, 1984.
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View of an unidentified party-goer in a Pierrot clown costume during a Halloween party at the nightclub Studio 54, New York, New York, late 1970s or early 1980s.
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Portrait of a unidentified, costumed party-goer at a Halloween Party in the nightclub Studio 54, New York, New York, October 1981. He is dressed in a plantinum blonde wig, white facepaint, a white bow tie, a lace bustier, and black underwear.
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Drew Barrymore during Halloween Party at Visage in New York City, New York, United States.
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Christopher Walken and Ellen Greene during Halloween Cast Party for “Little Shop of Horrors” at The Palace Hotel in New York City, New York, United States.
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Actress Brooke Shields and friend Stephen Bianucci attend Regine’s Halloween Party on October 31, 1981 at Regine’s in New York City. (Photo by Ron Galella/WireImage)
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Singer/Actress Cher and boyfriend Rob Camilletti attend Cher’s Halloween Party to Promote Her New Fragrance “Uninhibited” on October 31, 1988 at Century Paramount Hotel in New York City.
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View of costumed clubgoers on the dance floor during the third annual Halloween party at Studio 54, New York, New York, October 31, 1979.
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A woman dressed in a harem outfit dances at Studio 54 Halloween party, New York, New York, October 31, 1979. Behind them is an oversized version of the magazine cover that features Harry.
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A woman dressed like a Playboy Bunny dances at Studio 54 Halloween party, New York, New York, October 31, 1979.
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A woman in a garter belt and stockings dances at a Studio 54 Halloween party, New York, New York, October 31, 1978.
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A man, dressed only in a clear plastic sheet, dances with a topless woman at a Studio 54 Halloween party, New York, New York, October 31, 1978.
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Model Paris Hilton attends a party at Guy’s nightclub October 31, 2000 in Los Angeles, CA.
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Actor Jamie Foxx attends the Nightmare on 5th Street Halloween Costume Party October 31, 2000 in Santa Monica, CA.
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Model Lydia Hearst Shaw attending Third Annual Heidi Klum Halloween Party on October 31, 2002 at Capitale in New York City, New York.
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Young actress Michelle Trachtenberg arrives at a Halloween party in Hollywood, 1999.
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Jamie Lee Curtis in a witch’s costume designed by Nolan Miller in Hollywood, 1999.
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Chloë Sevigny at the Donovan Leitch and Kirsty Hume Annual Halloween Party at Serena in New York City.
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Donald Trump attending Halloween party thrown by Naomi Campbell and Kate Moss at the Supper Club to kick off Fashion Week, 1997.
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Actress Liliane Montevecchi attends Regine’s Halloween Party on October 31, 1985 at Regine’s in New York City.
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Actress Brooke Shields and friend Stephen Bianucci attend Regine’s Halloween Party on October 31, 1981 at Regine’s in New York City.
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Model Christie Hume and husband Donovan Leitch attending Halloween party thrown by Naomi Campbell and Kate Moss at the Supper Club to kick off Fashion Week.
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Rosie O’Donnell, Beth Midler and Martha Stewart arrive at a Halloween party in New York City, 1996.
