Do I look attractive?

The historical associations of maleness with power and femaleness with submission and frivolity mean that in the present time a woman dressing in men’s clothing and a man dressing in women’s clothing evoke two very different responses. A man dressing in women’s clothing is symbolically castrating himself of his phallic privilege. A woman dressing in men’s clothing is symbolically laying claim to the power of masculinity, a marginally more acceptable activity.
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Some people dress in women’s clothing as a way of expression. Some of these individuals are entertainers who dress in women’s clothing during performances, but live life as a man dressed in men’s clothing. Other individuals identify as a gender other than their birth gender.

This identity can be expressed simply by dressing as a woman (see transvestite) or through sex reassignment surgery.