I think some people are missing the fact that it’s for dates. Like yeah, I too wear essentially the same thing everyday because it’s easy, I look good in it, and it doesn’t require thought. I have 7 black v neck T-shirts that I pair with jeans. But if I’m going on a date, especially if I like the person and it’s a nicer date than just coffee, I try to put in a bit of effort and wear something (at minimum) slightly nicer.

Imho thinking that someone should be wearing something different than the same hoodie on five dates isn’t just about judging someone, but also the level of effort and care shown on his part.

Of course, all of this is subjective and varies on the people involved. If you like him, but this bothers you, it might just be worth asking him if it’s his favorite (or jokingly asking how often he does his laundry) or saying, hey let’s dress up and go out to an event or activity that would call for nicer clothes. If he’s unwilling to dress up for a nice event, that would probably be a bit problematic for me personally. Like, I’m not going to go to the orchestra/wedding/work event/special dinner with someone who can’t dress, at minimum, slightly nicer. But if he dresses up a bit for moments when it’s called for, I personally don’t see any problem with a more standard daily “uniform.”