Interesting POV tethers. I hadn't considered that angle. Definitely worth thinking about it. There is certainly some truth in the idea that girls being 'tomboys' is considered a good thing while 'girly' boys are still held up for ridicule.
I have never discouraged either of my DC (boy and girl) from choosing/wearing whatever it is they like. They are both very much into pink and glittery. I got a bit sniffy with a neighbour the other day because DS chose a pink Hello Kitty toy and her comment was along the lines of "what do you want that for? Are you a girl".
School may be a bit difficult because while I don't want him to change, I don't want to set him up for being bullied either, and the sad fact is that there will be more kids and their parents who see this is as weird than won't.
Haven't quite worked out how I am going to reconcile the personal with the political yet ? I think I shall probably cave in to some extent in a bid to protect him, though I hope I can do so in a way that explains to him about it and that he shouldn't feel ashamed in any way but just recognise that others are narrow-minded about these things. To some extent he'll negotiate his own way I guess. In his final year in nursery he had noticeably more 'masculine' behaviour at nursery than he did at home. He was already aware of roles and altering his behaviour to play different roles in different situations. Can't decide if this is terribly clever or terribly sad TBH - or maybe both?
Interestingly, DD has always steered clear of dresses and impractical shoes. While she likes pink and glittery she's so active that she detests anything that restricts her movements in any way. I have had to buy her boys shoes and stick 'jewels' on them on more than one occasion. The over feminisation of girls shoes does bother me. Glittery, sparkly etc are ok. Flimsy and downright bloody dangerous (many have very very slippery soles and straps that don't support the foot and encourage a turned ankle because the sole of the foot slides on the sole of the shoe) annoy me intensely.
In other ways my DC tend to conform to gender roles - DD loves dancing, DS loves kicking a ball around. But then they both love colouring/painting for hours on end and they also both like helping me with DIY (so much so they both have their own toolkits).
I don't always succeed but I tend to let them get on with it in their own way without thinking of gender roles at all. I believe that being the best person you can be is about playing to your own strengths, being aware of your weaknesses, and having integrity. Can't see that any of those things are affected by gender.