Well this has certainly got everyone going!!!
I have 3 boys. Ds1 (11) loved dressing up at playgroup, but really didn't express a wish to wear dresses outside of 'dressing up time'. He is a boy who now loves computer games, martial arts and the like.
Ds2 is 2. He is probably more girly than ds1 ever was in that he has a doll (bought for him when ds3 was born) and has curly blonde hair, so people often mistake him for a girl. He also likes prams and goes for the girly things at friends houses, as did Ds1. In fact he could easily be passed off as a girl in a dress.
He hasn't expressed a wish to wear dresses either, but he doesn't have any sisters dresses to steal. I honestly don't know what I would say if he did want to! At home, no problem at all, outside...well I would hope I am liberal minded enough not to care what others think as he IS only 2, but I really don't know.
And ds3 is 6 months, so he doesn't care what he wears!!!
Do all of these little boys here who like wearing dresses have sisters? Or are the dresses bought for them? I wouldn't buy a dress for my ds's.
If I saw a little boy in a dress I would just smile and think he was cute, nothing else. I don't believe them wearing dresses will have any bearing on who they are later on in life.