I have never in my life dressed as a typically female person, at least not since infancy and toddlerhood. When I was a very little girl, Paul Bernardo, the first Canadian serial killer, was on the loose in the area I was living in at that time. He was sexually assaulting and killing young girls. It quickly became typical for mothers to dress their daughters in boys' or very unisex clothing, until such time as he was caught. At about this time, my mother realised that she could save money on clothing by buying me boys' clothes because my brother, two years younger then me, couldn't wear girls' hand-me-downs (yay gender stereotypes) but it was more acceptable for a girl to wear boys' clothes.
She always made sure I owned one dress for formal occasions, but that was it.
My one feminine feature growing up was my hair. When I was 8, I got my hair cut very short (mum decided that I was old enough to choose my own hairstyle, so long as I did not cut my hair myself) and I actually passed as a boy with ease. It interested me, but my biological father was furious at me being called his "son" and threatened me with being removed from my mother's care and never seeing her again as long as I lived if I ever cut my hair again. As a result, I refused to have my hair cut for a long time. When I announced at 18 that I was going to shave my head and donate my hair to charity, that was the first time in my life people called me pretty.
I had hair down to the bottom of my butt and people in grocery store line-ups had been petting my hair and telling me my hair was pretty for years. It was only when I started telling them that I was shaving it all off that they started saying "But you're so pretty! (as opposed to just my hair) You'll look awful bald!"
When I shaved my head, I was again mistaken for a boy (by this point, I was wearing my brother's hand-me-downs as he had grown larger than me) and people, when hearing my voice, would automatically start apologising for thinking me to be a boy. They would fall over themselves with apologies and tell me that I'd be pretty if only I hadn't shaved my head.
Every time in my life that I've been told I'm pretty, it has been in the context of "You'd be pretty if only you... (fill in stereotypically female behaviour such as dressing like a girl, wearing make-up or growing out my hair here)."
People who understand my gender situation, however, seem to be more likely to tell me that I'm hot and gorgeous and that I'm actually good looking, without qualification. I don't know whether they're just being nice, or if their knowledge that they don't HAVE to put me into a gendered role is allowing them to appreciate my looks.