Fattish right now. I don't think I've ever been at an optimal weight for me, even though I've always fit in quite well into the average sort of population. I don't find it hard to find clothes, but I am affected enough that I don't wear short sleeves or shorts very readily and I tend to want to hide behind sweaters etc. I don't remember the last time I've worn a swimsuit.
Mostly it comes down to being more active. I know that when I am more toned those feelings of discomfort go away. I've never gained a whole lot of weight at once, but every year it's between 3 and 5 pounds more and so depending on my activity level that can really impact how I look.
I have a kind of bottom heavy hourglass shape (not pear, because I have a fairly proportional chest to the rest of my body). Weight loss/gain doesn't tend to gather on one particular area on me, which is both a good and a bad thing. It at least isn't immediately visible when I gain five pounds, but it also means I don't feel like I have one particular body part to showcase that looks spectacular. I don't really like how I feel or look right now, as I know it isn't healthy, but have been on a regular exercise routine for two weeks and hope to change that feeling over time.
Strangely enough, even though I'm self-conscious about wearing certain things or how I look generally, I've never felt that way around anyone I've been involved with and I've always had positive male feedback so weight has never been an issue in that regard.
I was awkward looking/feeling when I was 12, 13, 14 and it took a long time to see my body in a more realistic light, even after I had grown and thinned out and gotten more proportional. Now, weight isn't something that I would often even mention to others about being unhappy about. I realize I need more personal routine and discipline in my life and that most things that bother me are within my own control. The things I can't change, I think I've come to terms with pretty well, so I'd say I'm basically happy with my body, even though I need to make some improvements.
I think a lot of my body image in the past was shaped by having a mother who was very naturally shapely, with a well-balanced hourglass figure and thin without ever working out, as well as comparing myself to my older sister whom I deemed perfect and who was a much smaller version of me.