I saw this trend as early as 2004 and 2005 (see the four images at the bottom), but there is a big difference between then and now. In those days men usually had to make do somehow if they wanted to wear skirts, dresses or dress-like garments.
Some men still use creative solutions like wearing a traditional kaftan (see below left), but now established brands also offer skirts and dresses specifically made for men.

A kaftan (left) is a creative solution to the dearth of male skirts and dresses. The person on the right wears a dress made by Japanese fashion brand Comme des Garçons.

Skirts. The one on the right is by Comme des Garçons.

In 2005, some men still had to resort to wrapping shirts around their waist (right) to make them look like skirts.

Back in 2005 Yohji Yamamoto used to sell a dress for men that was advertised as a “long sweater” (left). These days it could be sold as a dress without men feeling uncomfortable about it.
I am wondering whether it is easier for Japanese men to break through this taboo than it is for many Western men. After all, Japanese men are used to wearing the dress-like yukata.
The yukata virtually disappeared from the Japanese street scene after the end of WWII, but it has become very popular again among young men during the past ten years.

Young men wearing fashionable modern yukata.
What is your take on this?

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