Let the rights over my brother's sartorial direction between me and his wife commence. I bought him an 8-panel hat for Christmas because he's got the facial bone structure that's well complimented by most hats. His wife hates it, though. Meanwhile, he wore this awful earth-tone-colored knit yesterday that she gave him. Besides the nasty color, it didn't fit him well at all. It's total old-man garb, only not in the SF-approved sense. More in the "What steeze-less corpse did you pull this off of?" sense. Not coincidentally, it belonged to her grandfather.
I'm sure I've mentioned it before, but this is all a shame because he's got the ideal proportions (broad shoulders, trim waist) for a lot of clothes to look really good on him.
Ultimately, it matters more what he (and I guess she) likes, but I die a little each time I see him wear something like a boxy pea coat, dad jeans and white Puma sneakers.