I started wearing heels when I was 10. No joke. I had a huge complex about my height, and I got my mom to buy me heels. Quite high. And I somehow immediately knew how to wear them. I think women have it easier, because we kind of "practice" in our moms' and grandmas' heels since we learn to walk. It was my favorite thing to do, to stuff my grandma's old heels with something and wear them around the house.
Some women, on the contrary, never learn. Sometimes I cringe when I see them walk in them. You can't think about it, it has to be natural, otherwise you look stupid.