Retro Halloween Drag – Remember when Men were Women and Women were Men?

Modern Halloween is all about becoming a different character. It’s an opportunity to take a chance, to explore another reality, or to flout social convention. Since people began dressing in costume for Halloween, many have opted to examine – even if only for one night – the mysterious creature that is the opposite gender.

Yes, for many decades, men in particular have enjoyed actively transgressing expected gender roles on October 31st. They have relished putting on pantyhose, a dress, high heels, and a bra (often padded to depict an unusually ample bosom) as they strike out for the nearest Halloween party. It seems that the more amplified the man’s testosterone level, the more likely he will choose drag as a costume. For example, many of the football players at my high school went the drag route, often portraying not just women, but über-feminine cheerleaders.

Are these men frustrated by society’s rather narrow definition of what it means to be “masculine”? Are they interested in exploring their feminine sides? Are they conducting a social experiment to better understand how the other half lives? Are they mocking women with their display of larger-than-life features? Do these men simply enjoy manipulating their own faux body parts? Or maybe dressing in drag is just easy and economical since most males have mothers, aunts, sisters, or girlfriends from whom they can borrow rouge, mascara, and a plus-size cocktail dress?

Whatever the motivation, gender bending in honor of Halloween – no matter how homely the costumed character turns out to be – has been a tradition through the ages. Check out these fine specimens…

1935 – Image from Trevira

1946 – Image from aviatorr727

1956 – Image from elston

1969 – Image from kevynjacobs

1971 – Image from

1974 – Image from High Steel Heels

1976 – Image from kevynjacobs

1978 – Image from Mr.Martee

1980 – Image from smays

1980 – Image from VTscapes

1981 – Image from Harold Gee


Don’t look at the dogs, work the lock! You looked at the dogs!

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4 thoughts on “Retro Halloween Drag – Remember when Men were Women and Women were Men?

  1. I tried to find a picture of the football players from Revenge of the Nerds dressed as cheerleaders, but haven’t been able to find one online yet.

    I’ve only dressed as a woman once. In the late 90s, I attended a Halloween party dressed as Monica Lewinsky. Fortunately, no pictures of the party exist.

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