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.
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.
Dont hurt his feelings If you don't like the way he dresses then you shouldnt have got with him. Sounds like you care about appearances more than he does. Leave him alone and keep dressing nice he will eventually start to notice and if he doesn't then just love him the way he is.
I love it when guys dress wack...it shows they have some character...why would you want your boyfriend to look like every other guy that walks around at the mall? I'm trying to get my boyfriend to dress wackier:P
go to the mall with him and suggest outfits you'd like to see on him. don't put him or his style down, but encourage him to wear some of the things you like. be like "damn baby you look really good in that shirt" and then kinda be all over him. it might be the push that he needs. or when you go out pick up a few things u'd like to see him in. but be prepared for him not to listen and still dress like that anyway!