In a ski town like Whistler, or I would assume Vail and places like that... you can probably get away with. But anywhere else though? You look pretty stupid.
I kinda disagree with your word choice there though....
Well, you can't have skin-tight jeans and a shirt that's to your knees, or else it actually does look like you're wearing a short dress with tights on, and high-tops don't really help your cause. However, if you've got baggy jeans with a tall shirt and/or tall hoody. But to everyone their own.
graphic tall t + tights is my go to studying outfit. super comfy and they don't get excessively wrinkled the way my skirts and most of my dresses seem to. I'll wear them to class and even grocery shopping occasionally but don't consider it anything more than casual wear, basically a sweatpants equivalent