Men wearing skirts is not a new concept
There is a long history of men throughout several cultures wearing either skirts or dress-like clothing and it has never been perceived as strange.
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Whether it is the kilt of Scotland and Ireland or the gauzy wrappings of ancient Egypt, men wearing skirts or skirt-like clothing is not a new concept. Skirts offer great ease of movement for the wearer, but they are also incredibly simple to construct and wear (even wrapping a towel around one’s waist out of the shower is technically a type of ‘skirt’). With the introduction of hosiery in 15th century Western Europe, pants and more highly tailored clothing become more commonly worn by men and became a sign of “masculinity.” The argument that because our Western societies currently view men in skirts as problematic or emasculating because “that’s how it is,” is inherently flawed. All it takes is a simple search to find thorough documentation of men wearing skirts, dresses, tunics, and togas far back throughout human history. It is uncommon for commercial men’s clothing today to be sold with highly ornate details or bright colors because that is the current fashion trend, but it was only a few hundred years ago that men were practically peacocks in elaborately embroidered clothing in bright, flashy colors. Styles change, fashion changes, and so can society’s thinking about who can wear what.
Just because there has been a history of men in skirts and dresses doesn't mean there isn't a reason they don't wear them now. Styles do change, and usually to accommodate the wearer more appropriately. It's safe to say that the massive powdered wigs of the 18th century would not be appropriate to wear today, even if they were commonplace then. Men's clothing today reflects the type of clothing that men are interested in wearing, and at present, it does not include skirts.