I go out in women's clothes as a man all the time..... BUT it's not obvious. I wear only women's jeans and socks (if I must wear socks), nearly all my tank tops are racerback, and I have some women's T-shirts that aren't too obvious to someone not looking. I also have several pairs of women's canvas shoes with patterns you'll never find in the Men's section. I wear these things to work, to the sports bar, to the airport, etc. But I still look like a guy, probably no more odd than a guy wearing a Hawaiian shirt.
