Would it bother you if your husband looked like he slept on the streets?

My husband very often wears clothes that are 20 years old - tattered with holes. He has been mistaken for a homeless person on more than a few occasions. It’s not that he’s unfashionable or mismatched, he just looks like he’s been sleeping rough for a while and definitely catches a few glances. He is a beautiful looking man, has great hygiene and more than enough money to wear whatever but chooses to dress this way for some reason, he says he feels comfortable and doesn’t care if people judge him etc makes him more determined to show up to a fancy restaurant or hotel or designer shop or whatever like he walked off the streets and order the most luxurious thing (I don’t understand this mindset either). I didn’t mind so much until we had our son and it started to bother me. For me, looking presentable or making an effort to look presentable for your family is important to me (which he knows) I feel like it’s a massive F U when he dresses this way but at the same time I hate myself for being judgey and should just be happy he is happy. I never want anyone to judge my son or for him to be treated differently for it (which they will probably). Would it bother you? And what would you do?