There are a number of reasons why men wear high heels, an accessory typically associated with women in our culture. Men may be exploring the experience of wearing unfamiliar shoes, wearing them for their own entertainment and that of others, or they may be expressing their underlying feelings about their own gender.

Imitating women, either by oneself or among male friends, is not uncommon. Playing with the taboo of gender boundaries can provide men with amusement and can be a form of either mockery or veneration for women as well as socially constructed gender standards.

Some men professionally or occasionally dress as women and perform for their own amusement and that of others. Drag, which includes the wearing of extreme examples of high heels, has a long tradition in the gay community, but drag is also performed by and for heterosexuals.

Men may simply wonder what it's like to wear and walk in high heels; for anyone who's never done it, it seems very difficult and possibly thrilling. Men may also wonder what effect fashion standards have on the comfort of women.

Transvestites are people who dress in clothing generally deemed appropriate for people of the opposite sex; most transvestites, according ub-counseling.buffalo.edu, are heterosexual men. Cross-dressers may derive a sense of peace or of sexual pleasure from wearing opposite-gender clothing or may actively be trying to push gender taboos.

Some biological men who don women's clothing such as high heels may be expressing a transgender identity. For some people, biological sex and gender identity are not aligned, and expressing one's true gender by wearing women's clothing and, for some, through hormonal and surgical treatments, is important for transwomen (male-to-female transexuals), according to apa.org.