This post sounds a bit braggy but i want to answer the question. I also forgot the exact OP halfway through and just went on a kind of random tirade about my looks through the decades, which nobody is interested in. But anyway...
I was chubby and weird as a teen and carried insecurity about that which impacted my self esteem. looking back, I'd actually suggest that I didn't have low self esteem as such but actually suffered from a sense of utter worthlessness. I just want to give 1999 me a hug and say 'its going to be ok!'.
I got a little male attention but rarely from the boys I fancied. In my early twenties I lost about 30kg and suddenly the boys who I knew from my teens were suddenly coming up to me when we were out, asking for my number and to take me out. I generally said no as i found them very shallow. I was concentrating on my studies and career for his part of my life but really wanted that validation.
Through my twenties I wasn't lacking suitors but wasn't A-list. My hair and style were never quite right but I was asked out a lot, . In my thirties, I was pregnant and breastfeeding for most of that decade, so don't think there were many men who were too interested (plus I got married at 30!).
I'm in my 40s now and finally seem to have grown into my facial bone structure, am still slim, know my style, have cracked my make up 'look' and am more confident than ever. I don't know what men think of me but my female friends and colleagues are always very complimentary and say nice things about how I look. I don't care about male attention any more so am very happy to be my normal goofy cringey self around men. I'd say my style now is quite 'fierce' (not sure if that's the right word!) I do think my look can be quite striking but it's just for fun and I'm still a massive dweeb inside. I think I'm funny and kind and I do think I have a gift for interacting with people.
I would say I'm very socially confident, very much a people person but I do actually trace this back to the teenager who was eccentric and never got the guy. I never got by on my looks alone which actually was a blessing. I do think I can often spot attractive adults who weren't necessarily pretty as teens as they tend to be self depreciating and their identity isn't about being good looking.
My kids are beautiful (of course I'd say that) and I tell them so, but also tell them that the real, true beauty lies inside the heart; kindness, honesty, integrity. Old fashioned values such as hard work, resilience, humility will stand them in good stead through their lives and physical beauty is just something fun to play with if you have it. I'm trying to get them not to place a huge value on looks so that they have other stores of confidence to draw from. My idea is that their cup will be full enough to survive the teen years without feeling as undeserving and as lost as I did during that wilderness.