We've been together 20 years. When we first met he wore jeans and t shirts and looked nice.
About 7 years in, he started wearing more eccentric outfits, until I eventually gently told him his outfits didn't work. He was hurt and upset and I felt bad, but he seemed to stop the worst combinations.
Since then he wears his weirdest stuff when he goes out on his own, but sometimes I'm embarrassed when we're together, because he still wears odd combinations.
Tonight when he went out DS told him he looked awful and I've been cringing about the looks he'll be getting as he walked into town.
I don't know what to do - on the one hand I think people have a right to wear what they like and don't want to hurt his feelings by bringing this up again. But on the other hand I want to feel proud of my DH and to fancy him, but I can't when he looks so silly.
It would be very outing to describe his outfits but try and imagine if someone had thrown together some very loud items, vintage 70s items, clashing patterns, over the top accessories, a hat, and some worn stuff with holes in all together in a crazy mismatched way.