AI-generated image of a man in a skirt and heels with a woman in a dress and heels
May 13, 2025

The term “crossdressing” refers to people of a specific gender who wear clothes that are considered by most of a culture to belong to another gender. But should wearing them really be considered crossdressing in our modern society where discussions of gender and the breaking of gender norms are more prevalent than ever? Isn’t it time we redefine what “crossdressing” really means?

Let’s start with the current definition of crossdressing from Wikipedia:

Cross-dressing is the act of wearing clothes traditionally or stereotypically associated with a different gender. From as early as pre-modern history, cross-dressing has been practiced in order to disguise, comfort, entertain, and express oneself.

Socialization establishes social norms among the people of a particular society. With regard to the social aspects of clothing, such standards may reflect guidelines relating to the style, color, or type of clothing that individuals are expected to wear. Such expectations may be delineated according to gender roles. Cross-dressing involves dressing contrary to the prevailing standards (or in some cases, laws) for a person of their gender in their own society.

The term “cross-dressing” refers to an action or a behavior, without attributing or implying any specific causes or motives for that behavior. Cross-dressing is not synonymous with being transgender.

Wikipedia

According to this definition, a man wearing a skirt, dress or heels is crossdressing. In fact, a woman putting on a checkered, button-up shirt would also technically be considered crossdressing even if it is much more acceptable than a man in a dress. Both of those examples are, in my opinion, quite unfortunate. We don’t need to label those.

Instead, I think we need to redefine what crossdressing means. My suggestion would be to use the term only to describe a man who is dressing himself up to temporarily pass as a woman or, of course, a woman trying to temporarily pass as a man.

Social media is full of photos and videos of people who do this as a hobby but don’t necessarily feel like they are transgender. Men who do this typically take on another, female persona with a new name and essentially, a new identity. That is in contrast to men who just wear skirts because they like them, but still want to be themselves.

I have absolutely no problem with men who want to become their female alter ego and pass as a woman. Some of them do a spectacular job of it, too, and I have to admire that. However, since the intention is entirely different than that of a man who just puts on a skirt in summer because it’s cooler or he wears tights because he thinks they make his legs look great, I think we need to separate the terminology.

In fact, I would argue we don’t need any special word for it. Why can’t a man just be a man who likes wearing a skirt without any sort of label? In the end, they are just clothes, and the man wearing them is just the man wearing them. You don’t need to call it anything special.

What do you think about redefining what it means to crossdress? Do men who like to wear skirts or other clothes found in the women’s department really need a specific label? Let me know in the comments!

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About the Author

Alex Seifert
In many ways, Alex is a typical man who just so happens to enjoy wearing skirts and high heels. He is married to a wonderful, supportive wife and has a young son. His hobbies include reading, programming, metal music, playing instruments, video games, cars, hiking and a number of other smaller things.

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