I'm loving this thread.
I've had body image issues for years. I'm only 31, and the last few years I've always covered up. I've definitely fallen for trap of the more you cover the smaller you look.
There's pictures of me, where even if I'm technically the slimmest in group, I look the widest as I'm wearing cardigans and baggy t-shirts.
I went out to walk the dog yesterday, and it was warm. I wore a hoody and baggy joggers, I walked with a lady maybe 10 years older than me, wearing shorts and a little vest top with a little pot belly sticking out, and you know what? She looked great, confident & effortless. I noticed the pot belly, but just in the same way I notice anything, neither good or bad, just there. I went home and thought about all the simular clothes I have and just thought, I just can't, but wish I could.
I'm finding a middle ground for myself, I'm gonna order lots of bright colours, play suits, dresses, as opposed to blacks & dark colours I always wear. I'm going to brave getting my legs and arms out first, as opposed to always wearing pants and jackets no matter the weather. Then brave wearing more clingy / strappy clothes.
I'm going to a wedding next month, instead of getting a sleeved flowy dress, I'm going to wear a fitted dress.
It's ridiculous, the only outfit I deem looking good on me is when I don't have any lumps, bumps or shape on show, but when I see much bigger people than me, wearing lovely bright and fitted clothing, I think they look great and it wouldn't occur to me to think they'd look better covered up, I just struggle to apply that logic to myself.