Distressed when picking clothes

I was wondering if anyone else had any experience with the following. I keep having these feelings of not "feeling right" in my clothes. I have always enjoyed fashion and I enjoy looking at others choices of clothing and thinking about why they chose them etc. Anyway, I have a quite a bit of clothing I bought because I loved it but then when I put it on to go out in it, it just doesn't feel like me at all. It's mainly skirts and dresses I have an issue with. I feel weird every time I put one on like I feel too feminine and it's not right. (For context I am a cis woman.)

Has anyone else had that kind of feeling before? I'm confused because it causes me a great deal of distress when I'm getting dressed - which I don't want! It's not a sensory thing, I'm sure of that, as I don't buy clothes that are uncomfortable to me.

Its also worth noting I do have big struggles identifying emotions. 

  • I wear dresses, but hate the feel of tights so wear the dress over trousers instead.

  • Yep, I often feel and look like an overcoat on a wheel barrow, I think a lot of clothes are poorly constructed and not really made for the human form. I'm a size 18-20 on top and find tops that are wider than they are long, just about cover my bust, have armholes that would fit a broomstick and the bust darts under the armholes. When I can get trousers that are long enough for me they often don't fit in the rise and have waist bands more like hat bands. I gave up wearing skirts and dresses ages ago as I can't get tights to fit my long legs and stockings are more like over the knee socks. Most of the fabrics are nasty and in horrible patterns. I would like to have a better relationship with clothes and to be able to afford them, I can't believe people have to pay so much for such rubbish. I've sometimes thought abut going on one of those programs, like with Gok Wan and give him the challenge of finding trousers that fit me on the high street, becuse I don't think they really exist.

  • I do this with skirts and dresses as well. I buy them because I think they’ll be nice if I get invited to a party etc but I rarely end up wearing them. I’m much more comfortable in trousers. I’m also not sure why though, they just don’t seem to suit me for some reason. Even as a teen I would only wear skirts to school and at ballet