Skirt Cafe is an on-line community dedicated to exploring, promoting and advocating skirts and kilts as a fashion choice for men, formerly known as men in skirts. We do this in the context of men's fashion freedom --- an expansion of choices beyond those commonly available for men to include kilts, skirts and other garments. We recognize a diversity of styles our members feel comfortable wearing, and do not exclude any potential choices. Continuing dialog on gender is encouraged in the context of fashion freedom for men. See here for more details.
Heinz Nerich Windermere, a prince (later king) from the anime Macross Delta wears an outfit that includes a skirt:
He just looks femenine even by anime standards and is voiced by a female voice actress. It would be interesting to see someone cosplay him, maybe the boys who dress up as princesses for Halloween might want to give it a shot .