My thoughts on this are really ambiguous and messy. There are so many complicating factors. I think mainstream physical beauty is a kind of giftedness, like being smart or athletic or musically gifted, or anything else. Even though I want my children to be smart, I don't necessarily think that promoting intelligence over beauty as more worthy, when not everyone will have a higher than average IQ for a number of reasons, including how society defines it. Of course you have to acknowledge these kinds of giftedness, and as parents we have to interact with our children in the way that helps them best navigate these complicated waters and turn out to be kind and well-adjusted adults.
Beauty as a gift seems the most nebulous, I guess because it is so subjective, and because it changes. Many children are beautiful when they are younger, like under 8, but it's difficult to know if they will garner that same attention as they get older, and probably they won't because I think people are more willing to compliment younger children than older ones in this way. And then there is what I think of as that awkward phase that lasts for a few years, and that's probably crucial with the self esteem thing.
It honestly doesn't seem to matter if you're beautiful if you believe that you are at least attractive and worthwhile. I'm sure we've all known beautiful but self-doubting people, and really confident people who were attractive and had a certain flair, but that were maybe not that conventionally pretty. That internal belief is a different thing from the external reinforcement, and that type of reinforcement can have it's own problems. So I guess just acknowledging that you think your child is beautiful, other people may think s/he is beautiful and may make comments; then there is the flip side that others might not feel the same way, they may say negative things. I think it's hard to know how to trust some of the things people say, especially if they want something from you, but I guess that is best left for a later discussion.
I think showcasing what other cultures considers beautiful is important as well. I find that my kids often have a completely different idea of what pretty is and means than I do. My older daughter and I don't agree on who we find pretty, and sometimes there are children I find breathtakingly beautiful that other people seem to overlook. When my daughter was younger, I noticed other parents in my AP/NFL circle of friends would tell their children as beautiful or cute often in the course of playing with them, and then I started doing it because I didn't want people to think I didn't think my children weren't cute. :lol But I don't remember hearing this when I grew up.
When I saw photos of myself as a baby, I thought I was cute, so I asked my mom if people thought I was, and she said yes. But basically I've been fat all my life, so it was always made very clear to me that I wasn't pretty. For some reason, a glutton for punishment, when I was definitely not pretty (like 11 or so), I asked my older sister if I was pretty and she said, "you're pretty in your own way." I knew that absolutely meant I wasn't pretty, and that the rare time my mom would say something indicating I was, that she really was lying because she was my mom.
I have tried to come to terms with not being pretty. Over the years I've tried to embrace being ugly as a powerful, self affirming kind of thing, but sometimes I really believe it and it gets me down, which just seems downright shameful considering how blessed I am in life. I take lots of photos of myself, trying to find good ones, but I don't throw away the bad ones either, and I keep the not-so-attractive ones of my children as well as the ones that I think put them in the best light, although I pretty much don't show my older daughter the ones I think she won't like, and I will delete photos if they ask me to. But just today, I showed my daughter a cell phone pic I took of her on her birthday, and I was surprised that she liked it. She thinks she is ugly, and she's not. She hates her nose, and I can understand that, but I think that she has a good nose that she will look really good on her when she grows up a bit. So I try to be honest, and she's honest back (yeah, I'm glad I don't have your nose, it has way too much cartilage in it).
Anyway, today I was taking photos of myself, for some reason, and I was looking at all the things I hate, the more recent things due to age, and I was wondering why in the heck I'm so ugly, but then I honestly did start to think that maybe I'm not, maybe there is a kind of beauty in all things. I really would like my daughters to have more confidence in how they appear to others, both physically and intellectually, because I do think it hampers your life to be so inept in the things that society values. But I think kids are least likely to believe their mothers can be objective, so I'm not sure how to handle that.
ETA: I'm not really sure how to navigate this with my children, because I think ultimately I want to downplay the idea that being pretty really matters, but somehow it mattered to me and I don't think this was the type of thing promoted in my day and age. I get criticized by my family when I say things that indicate I don't think my children are beautiful enough, but in some ways my kids seem pretty sanguine about it. My 7 year old doesn't seem to notice it at all, and my 12 year old can seem to criticize her looks without taking it too seriously--I mean she seems to get where it goes in the grand scheme of things, but it's hard to say how it really influences her.
I think it's interesting, however, because my sister is the one who gives me flak for not telling my kids they are beautiful or seemingly not recognizing that they are smart, but her grandkids are stunning and seem pretty bright to me, and it's not like she waxes on about it to them. So I almost wonder if she's overcompensating, or if it's just she lives with her grandkids and I live with my kids, so we are both used to them and we feel they are under appreciated, or something.