I would say yes, and it took a bit of poking and prodding to get him there, but it has been worth it. I LOVE to shop for men's clothes, it's so much easier, so much less fussy (which is probably why my son has started to develop an excellent sense of style!). It started with my buying DH a few things here and there (and I mean little things, like a tie that wasn't so stuffy). I tried my best to educate along the way "this style tie is popular because XYZ" or "this color shirt is OK with said tie and is not too bold or loud". I'm also a shoe freak, so I would buy him nice shoes too.
We worked our way up from ties to blazers, to pants, to the fancy men's shop which does custom alterations. I bought him a "no exchanges, no returns" gift certificate and told the guys in the store what to expect when he came in! After his tailored jackets were back, you could just see it in his posture and the way he carried himself. He's larger than average, but not quite taller than average, so Big & Tall clothes were always a bit off on him. Anyway, he started getting tons of compliments and I think he realized that he must have been off the mark before...since then, he's not questioned my choices once!
The other day, he wore a navy and white striped shirt with a royal blue and kelly green paisley tie, with matching DRAGON printed socks that my son picked out. The socks were royal blue with gray dragons breathing fire LOL! He said he got SO many compliments. My son picked the tie + the socks for his Christmas gift. I'm also pleased that hubby put the outfit together on his own! Years ago, he never would have worn a striped shirt, much less mixed it with paisley!