When I was reading that, I was wondering if he meant a T-Shirt with a big frowny face, or if he meant the shirt itself was literally frowning, as in it was old and beat up and drooping into a sad shape.
Both are equally bad writing, so it could go either way. But I honestly can't decide which is more pathetic. He either dressed his sad girl character in a sad smiley shirt because that's his entire concept of character development. OR he's just so bad at his effort to be descriptive that when he was trying to explain that her clothing was worn and tired, he somehow went with the word 'frowning'. It's like a mobius strip of failure, you can't tell where and how one part starts sucking due to lack of skill, because the skills relevant to the parts before and after are equally lacking. Just one infinite loop of being pathetic over and over, forever.
