offensive? I asked him if there is anything that I do that's annoying and he mentioned a couple things about my personality mostly having to do with my shyness.
I was just wondering if mentioning the clothes issue and how it kind of bothers me when he weard something really old looking on a date means that I'm trying to change him. And I think high socks with shorts just looks bad (it was winter when we first started dating lol so this didn't happen)
I don't need him to dress up but think he would look even better than he already does in clothes that fit better
Is mentioning the clothes thing worse than him mentioning personality things?
Nothing wrong with pointing out things like that about each other, but it's not fair to force change upon them. You should be able to take the person for who they are, not try to change them. Maybe he just doesn't realize what his dress sense is like. anyway there's nothing wrong with mentioning it but beware, men can be stubborn, don't expect him to just change because you don't like it :p he will change if he wants to.
also it's 'wore' or 'wears' not 'weard'! weard is not a word :p
It depends if it's really the clothes that bother you or if it's that he doesn't seem to want to make an effort to look good for you.
If the former, don't do anything, if the latter, have a conversation. Some guys are just really bad at dressing themselves. They don't care how they look unless it's for work, and so they tend to dress like slobs when they don't have to look professional. I'm dating just one such guy.
I've bought him presents of new clothes that I like, ties, sweaters, nice jeans, etc, but I'll never tell him what to wear. On the occasion when he was meeting some of my extended family I did request that he wear (and iron) a button down shirt and nice sweater, but that was because it was my family and I wanted him to make a good impression.
So, either put up with it or buy him some new clothes (but not all at once!)