I used to struggle with this problem, but now I wear whatever I want to. My main problem was that I really didn't like getting noticed/stared at, and my style seems to draw attention. I've finally just been able to ignore the stares and what other people think, and it makes me feel so good! If nothing holds you back, maybe you can give advice on how you came to that point!
Money haha - I mainly get my clothes secondhand online, or from charity shops and vintage fairs; but even so I don't have the cash to have all the clothes I'd like; if I won the lotto I'd buy so many 50s-styley dresses and pretty skirts and blouses.
Very occasionally my body type holds me back from wearing clothes I really like and think look great on other people. I feel lucky most of the time to have an hourglass figure which really works with my 'aesthetic' - I like 40s and 50s style clothes eg. full skirts that're high waisted so they show off my small waist and hide my larger bum and thighs. I also like to wear tops than show off my chest/ cleavage a little bit. If I try and wear 60s style dresses I tend to look like a bit of a sack of potatoes because they look better on more petite women with less in the way of boobage haha. Also trousers I tend not to look good in but they don't suit my style much anyway
I will very rarely buy anything that doesn't have sleeves or is backless because I have bad skin on my back and shoulders :( (also I think my shoulders are too big for anything strapless)
The weather means I can't wear a lot of my favourite summery stuff a lot of the time as I live in England
Some of my clothes I don't wear very much 'cause they're kinda showy or formal and I have nowhere to wear them to :/
The nature of what I'm trying to do or the environment I'm in. I love dressing up, but it's highly impractical to wear a ball gown to a ball game, so I don't. I also love wearing heels, but if I'm going to be out in grass or doing a lot of walking, I'll wear flats or gym shoes.
I wear what I want to wear regardless what others would think of it. I often get comments from my friends that I should try changing my style, at one point I thought of it, but still decided to go on what I usually wear. It's me who would feel uncomfortable if I do, so why care about them.
I've got an interesting answer to this one! The weather holds me back. I love wearing layers, I think I look hot in a tight black turtleneck. I like scarves, hats, gloves, boots you name it. I would wear it all year but I worry I get looks!!!