This is particularly fitting as I am in Ohio visiting my boyfriend. We've been together for three years, and I think some improvements have been made, though they've certainly been small ones. My guy is graduating from college this weekend, is an apprentice with a Luthier (aka he makes and repairs guitars), and plays rock music. So his style is very relaxed with a little bit of an edge.
I think most of his progress is a result of my comments (or nagging, in some cases). He's upgraded from completely ripped up chuck taylors to pretty decent pumas (and even made the decision to replace the last pair of pumas when they were too worn down), stopped wearing trucker hats (shudder), has a much better hair cut (I cut his hair because he's unwilling to pay for it and untrusting of anyone I'm willing to pay to cut his hair), and often wears clean, rip-free, dark washed jeans. This winter I managed to strong arm him into getting a new black hoodie, since he had worn his old one almost daily for the last 2.5 years and it was completely falling apart. AND he has always cleaned up well, he just doesn't do it often.
However, he hates paying for clothes so most of his shirts are t-shirts that are at least 5 years old and he got for free. He has a couple pairs of light jeans with MASSIVE holes in them that he's unwilling to give up, and still wears because he thinks they make him look rock n' roll (sigh...). He also likes to wear a studded belt (black leather, silver square studs) that I've gotten more ok with but am by no means a fan of.
What I find most fascinating about the whole thing is that he LOVES that I put time into how I look and what I wear, and sometimes has a pretty natural understanding of fashion. When I was boot shopping I ran several options by him, and he said that he liked the dark brown boots best because they were the same color as my hair and thus looked better and made outfits more complete! He also is very aware of which colors look best on me (and tells me when the color I'm wearing is good and why), and knows I'm not a fan of my short neck and will tell me which tops make my neck look longer. He loves how my look has evolved, and (even though he hates actually shopping) is usually willing to share his opinion of anything fashion related that I show him.
Anyway, I'm hoping over the next couple months we can start upgrading the t-shirts a bit... I'm certainly fine with his general look, but it's the quality of the clothing that is really holding him back. We'll still look a bit mismatched, but we're both going through transitions and in very different career paths, and I'm very ok with that.