It's a lot easier to look edgy or choose clothes that are "unflattering" (aka make you look bigger) when you are a smaller body shape. Same goes for conventually attractive/groomed.
However, I now love my horseshoe jeans which took some getting used to. (Tbf, they suit me much better than mom jeans or skinny jeans). I think I'm in the sweet spot of "ugly" clothes dressing in mid-40s.
I'm out of the male gaze and in-front of menopausal body-shape changes. I can truly wear what I like and afford to spend on clothes. I've got a statuesque body-frame with big shoulders, proportionally smaller waist, big bum/thighs and big hair so my dressing has always tended towards the dramatic but this is the first time I'm embracing casual.
I cannot get enough of ugly dad trainers. Plus horseshoe/carrot jeans, slogan sweatshirts and ugly, ugly fleeces with chunky gold jewellery. It's a look only other women appreciate. Much like the Mormon dresses with huge collars/or sleeves - another look I favour - thanks Ganni).
I have a pastel and gold bomber jacket which is complimented on by nearly every woman I meet, of all ages. No man has ever said one word about it. Not one.
My director did ask me about my Ganni leopard print tie-blouse. He was visibly shocked at the huge puffy shoulders in the office. However he's a good bloke and wanted to know where it was from as he thought his wife would like it (I could tell he was not sure). I think he got her one for her birthday.