I've known him for a long time and we just decided to start going out. his clothes never bothered me until the first time we went out a few weeks ago. I looked really overdressed and well put together standing next to him (and I wasn't even dressed all that great!) anyway I was just a tad bit uncomfortable. but he's a really great guy! . I really don't want to be shallow about it but damn. I KNOW guys really hate it when girls try to tell them how to dress too so I don't want to ruin things by going THERE.
Most Helpful Guy
Go to the mall together. When browsing stores tell him "wow, this shirt would look amazing on you" and other such subtle hints. Even ask him to try one or two things on for you. Talk up how good he looks in the clothes. Chances are he'll take the bait.3