This is my DH too! I haaaaaaaaate his wardrobe but he refuses to let me get him new clothes. I finally was able to get him new jeans this past Christmas. He asked for 501s. And this summer, before our Disney trip, I told him I wasn't going to be seen with him in his ugly shorts from the 80's so I bought him a whole new set of Docker shorts and threw out his old ones before he got home. I ended up really liking his new shorts, but most of the time, I have to tell him, "I got it on clearance for $5" so that he'll keep it! LOL!
My DH would still be wearing his 501s if they fit. He will go tdihrough and get all new work clothes and all new ties every months to a year but god frobid he wore anything else from this decade. I gave up buying him dockers,, shorts, jeans or polo shirts. He will ignore all the nice stuff time and time again and grab a frayed pair of jeans, an old tshirt and some kind of white old guy tennis shoes every time. I almost dies and went to heaven when he got some vans that were't white.