Hmmm... Sounds like I shouldn't.
Maybe if I went to Harajuku !

I always dress properly though, or atlest I think I do, somewhat anyway. Default outfit would be a suit jacket, shirt, tie, knesocks and a skirt (all black). Maybe I should post pictures? lol

One month without skirts is a looong time without skirts, and I'll probably see dozens of pretty ones when I'm there I'll manage, it's really not a big deal actually. It's not like I'm crossdressed 24/7.

Thanx for the input

Strange as this may sound, one of the things I really like about Japan, is that some Japanese aren't afraid to express themselves. I live in Canada, and some of the things some of the younger Japanese wear would not fly at all over here. I don't know how a foreign cross-dresser would be treated, but I see at least a couple of Japanese cross-dressers every time I visit Tokyo or Osaka. I remember the last x-dresser I saw was around Tokyo city hall, and even though you could very easily tell he was a dude, no one gave him any problems. I say go for it, if it floats your boat and as long as you're not being disrespectful, like doing it in a temple. It make it a more interesting place for everyone.

Post pics! Harajuko is a good place to dress more funky and out of the ordinary but you should have a pair of other clothes to wear when you get on the subway or go around the city. ^_^

I think guys look so attractive in sports clothes but being original is great!

This is getting somewhat confusing, some say I shouldn't, some say it's OK and some say I should do it.
The safe way would be not to do it, and I think I'll stand out more than I like to without doing anything special. I look so darn "Western" it's almost annoying. You know, blue-grey eyes, pale skin, tall etc.


As requsted miko-san. A couple of pics, don't mind my room. I'm a bachelor

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I'll only say that you look sexy!
Anyway you can dress like this on Sunday in Harajuku on the Bridge to Yoyogi Park. I think you look really cool.
The bridge across the train tracks from Harajuku station to Yoyogi Park is the best place for this outfit and it's full with tones of cosplayers.