First off I am 19, I'm a bigger girl but nothing major. When I dress to go to school I usually throw on basketball shorts a t shirt, straighten my hair, and then throw on a black hat backwards. I don't know why I like it I just do. Is this attractive to guys?
Second when I go out at night my favorite outfit is jean shorts that are a little on the short side but nothing major and a t shirt or fitted tank with furry boot slippers. They are brown and look like they could be made out of a real animal. I love wearing them, but is this attractive too?
You might look pretty in those outfits, but it would be thanks to your hair, face, and body. Those outfits aren't doing anything for you! There are so many comfortable clothes that are both flattering and fashionable, and they can take your appearances over and beyond!
1) Unless you have a sexy face, nope, you'd look too tough / sloppy (basketball shorts). I'd save that look for the courts, that'll be attractive because it's appropriate.
2) All sounds good but the furry boots could go either way, some like that and some don't. I think the ones that don't are more particular and the ones that like it either like those kinda boots or they're looking at the bigger picture, the whole thing but they don't really go into details. I think when you get older you'll find that furry boots won't work for you in Western cultures.
Basketball shorts look dumpy and sloppy and like you don't care. And people don't wear fur boots in the summer.