Like many of the others who've responded so far, I can relate to what the OP has said. I, too, used to hate the way I looked when I was growing up (I think it was just the usual childhood angst about perceiving yourself to be the world's biggest dork), and although my feelings about my appearance have since thankfully done a complete 180, more or less (I wish I could remember when and how that happened), I still have moments when looking in the mirror causes me anguish. I've had recurring problems with the "heartbreak of psoriasis" - something that's always going to give one's self-esteem a battering (thankfully, though, the condition in question has lessened greatly in severity with the passing years) - and don't even get me started on my hair!
While I don't need to dress totally en femme to feel pretty, I do find that if I go too long dressing like just another average guy, my self-esteem starts to suffer. I've got quite a pretty face (hence the change in my feelings towards my appearance), and I always feel that I'm letting my looks go to waste if I don't wear any of the more feminine-looking items in my wardrobe: things which really do bring out those looks. Also, if I dress like everyone else, I feel like everyone else in turn is completely ignoring me, which is always a blow to the ego.
Sometimes I wonder if so many of us feel ugly in guy mode because for so long now (probably since the Industrial Revolution), men haven't been encouraged to look pretty - that, indeed, for a man to strive to be anything more than merely presentable is somehow "wrong". It's that whole thing about how men are valued more for what they do than how they look, and how, even today in these supposedly more equal times, so much of a man's worth is tied up in his "earning potential" (hoo boy, don't even get me started on that one!).
