Guys, how should I interpret this and would you be mad if your girl did this as well?
Most Helpful Guy
It wouldn't bother me, because I know I have terrible taste in clothes. Any time someone has complimented me on something I'm wearing, it's an item that was bought for me by a girl.
In your case, it's possible that he has the money for new clothes, but that looking good in new clothes is a low priority thing for him. He doesn't care about his appearance.
You buying the clothes for him, kind of makes him feel weird. It's a little emasculating, and it's a little bit of you saying "Clothes matter, stop spending your money on frivolous shit and buy yourself a clean shirt once in a while"