The days of your mom dressing you are (hopefully) long-gone. What you wear is self-expression. If you're conforming to the expectations of others because you're worried what they'll think then you'll only live up to their stereotype.
I follow a policy of wear whatever especially at home where I keep it a consistent 71°F; obviously my outfit outside changes with the temperature outside. But as long as I'm comfy I generally wear whatever. Crop-tops + sweatpants? Of course. Skirts and knee-length socks? Sometimes. Baggy XXL clothes I bought from Goodwill? Any day. If it's something I feel good in then it's on the table.
Crop-tops + sweatpants were my fave when it was warmer; now that it's turned cold I've pulled out this long green maxi skirt that can be unzipped to three different lengths; since the longest length drags along the ground I only wear this section at home so I don't get it dirty; I feel like a warlock in robes with it on.
For me, the clothes I feel the best in are the ones I think I look the best in. Because I don't have fuck-huge arms yet I don't wear tank-tops often. I like how way my chest looks but not all the time so I don't wear anything with a deep cut. But somehow, despite bulking something like 20lbs, I'm still at 8% body-fat so my stummy looks decently lean which is why I'm fine with tops that show off my midriff.
Some people throw around this feel-good you can wear anything because fashion should be inclusive and accessible to everyone notion; I don't agree with this exactly; what you wear reflects you; therefore, dress yourself as how you want to be seen. If you don't care about this then sure, wear absolutely anything you can find that you feel comfy in. There are no reductionist one-size-fits-all philosophies in my view and that extends to clothing also.
I look up to those who cultivate their own Aesthetics.