Mine will comment, though was more often when we were meeting in person because there was more of my outfit to see! He's noted when I've worn new shoes, like, "Oh, those are new shoes" (generally sneakers, like Keds or Skechers) or had a new purse. Once he said, "Wow, a denim jacket, I haven't seen one of those in a while!" It makes me feel seen and like he's paying attention.(It's never anything like "That shirt looks good on you," which might feel different because I'm a hetero female, and he's a hetero male--well, I suppose he could be bi, but he's married to a woman).

The one time it bothered me a bit was when I wore distressed jeans, and he said, "Things so bad you have holes in your jeans?" It actually kept me from wearing them again because I figured he'd make that comment again, and I didn't feel like hearing it. It was a style choice, not a comment on my mental state! This was a few years ago--if that happened now, I'd just say, "Hey, it annoyed me that you said that, please don't the next time I wear distressed jeans." I'm more direct now.

We actually had a conversation once on his commenting on my clothing. He said he is careful when he does that, that he wouldn't with certain clients as it could make them feel uncomfortable. And he pays attention to a client's reaction and wouldn't mention it again if it seemed to bother them.