My mom was a wonderful seamstress, but she couldn't teach me; I was clumsy-fingered and she was short-tempered so it just didn't work. I taught myself to sew one summer when I was away from home and bought a old, old Singer for $8 (tells you how long ago that was). I just made stuff and threw it away until I finally figured out how to sew.
I sewed for years but then gradually gave it up. I was totally amazed at the price of fabric when I thought about taking it up again. I think it is a combination of amount of clothing available now (thanks to free trade) and the speciality aspect of the finer fabrics now. I can remember, and this is really dating me now, when polyester burst on the fabric market, and it was very, very expensive for the time.
Mostly in the last 10 years, I've sewn costumes for the kids; capes and tunics for LARPing, and cos-play things for Clare to wear to Anime conventions. In this area of the country, there are just too many outlet stores, and places like TJ Maxx to get clothing at prices good enough that it's not worth it to me to sew something similar.
I have a lovely sewing machine that I bought just after we moved here, but it's buried under stuff in the basement right now.
I learned to sew in Home-Ec in the 9th grade. My teacher loved me, because I'd actually READ the pattern instructions, and never had to bother her with questions.
Between thrift stores and cheap imported clothing, doing your own sewing these days doesn't make sense as a savings. Does allow for customization, which is kinda cool...but I don't think it's enough of a reason for me to be dying to do it.
I just wish I had more skills, that's all. ;-)