Most Helpful Guy
The shirt doesn't mean anything. My ex bought be an $899.99 leather jacket 6 years ago. I hate her guts to a point where I believe she deserves the worst death... But I love the jacket and can't part with it.
I'd be worried about them being friends on Facebook!
Most Helpful Girl
Is her picture on the shirt? Otherwise, I don't see the problem. Maybe he looks good in it. I would worry more about the fact that he hates her. Hate isn't the opposite of love. It implies he still cares about her in some way. I think he needs some time to heal. And to delete her from Facebook.