Considering the reaction you're getting out there, it sounds like it's working!
Really, I'm sure your social success has much more to do with the guy inside those designer jeans. It's great to make little changes like that that make you feel good.
I've gone the other way: always dressed like I was a kid (I love ripped jeans, owned almost nothing but black, stuff like that), but now I'm going for a more mature, put-together look. Still feel like I'm "dressing up" sometimes, though.
