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Cross-dressing laws can be challenged on various grounds. Cross-dressing may also be considered an element of trans identity protected under non-discrimination and equality guarantees. Early cases, however, dealt with the textual vagueness of laws that criminalised dressing in clothing of the opposite sex. One way in which law has played a role in enforcing gender norms is by prohibiting cross-dressing. Sumptuary laws were common in medieval Europe, Elizabethan England and colonial North America and served to regulate public attire according to occupation, class and gender.
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10 Lingerie Items Every Crossdresser and Transgender Woman Should Own

Cross-dressing in motion pictures began in the early days of the silent films. Charlie Chaplin and Stan Laurel brought the tradition of female impersonation in the English music halls when they came to America with Fred Karno 's comedy troupe in Both Chaplin and Laurel occasionally dressed as women in their films. Even the beefy American actor Wallace Beery appeared in a series of silent films as a Swedish woman. The tradition has continued for many years, usually played for laughs.
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The way I see it, if wearing lingerie is wrong for a guy, there are much worse things I could be doing. I didn't know what I was getting into when I slipped on that first pair of panties years ago. But once I started looking at catalogues and seeing bras, hosiery, etc.
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