We don't often see men who wear skirts, but I quite like the look. I think it looks rather rugged, if it's done right, and if the guy has a lot of self-assurance. I guess the deciding factor is no attempt at having feminine legs, with shoes that are unmistakably male. I've posted pics in many threads, but here are a few more:
http://4.bp.blogspot.com/_glFJiPFcSv...cobs-skirt.jpg
http://owlposse.com/wp/wp-content/up...tBostonCom.jpg
http://colleenanderson.files.wordpre...03/skirts2.jpg
http://thesocietypages.org/socimages...42a9fdae22.jpg
http://www.northwestcoin.ca/irenat01.jpg
http://www.dividedbytruth.org/images/sissy_in_skirt.jpg
I think these looks would raise a different kind of eyebrow:
http://realmenhavespoken.files.wordp.../menskirt1.jpg
http://t3.gstatic.com/images?q=tbn:A...A0XqXx8fAGC-pT
http://1.bp.blogspot.com/-jwwhKpc9BN...0/P1030521.JPG
http://images.sodahead.com/polls/000..._3_xlarge.jpeg
The first group portrays men who are not attempting to cross-dress or look feminine, but who are attempting to redefine men's styles. The men in the second group are still presenting as men, but they do cross into the feminine realm with the way they've put their look together. I think that people would be confused by this in a different way than they would be, just seeing some guy who wears something that looks like a kilt.
But, if you live in a conservative area, be prepared to raise eyebrows just the same:
http://myweb.tiscali.co.uk/talendor/skirt400.jpg
