I always thought that Star and Tom have never forget about each other because Star wears horns and Tom's shirt has a star on it. So I drew how they got it. It's times when Star and Tom were dating first time. As we know Star was a "rock-punk" princess and I guess Tom's style was official and he wore only costumes. But after he got that t-shirt from Star he changed a bit for her and started to wear more casual clothes. That's my headcanon!