I heard a comment by a contractor once that I thought was really good.
“Compliment the customer, but never personally”
I thought this was great advice. Maybe say nice book bag, or that’s a neat organizer. But as a male I would stay away from even clothes. In my work experience whether a compliment is creepy or not is highly dependent on whether the person on the receiving end likes the person on the giving end.
There was a group of women I worked with who thought Dr. McDreamy could say basically anything about anything to them and it was great. Another man could walk in and say “how’s it going” and they weren’t “respecting boundaries”.
So just as a male I aim to keep it very professional at all times in the workplace at least.
On a personal level (outside of work) POV I don’t think a clothing compliment is bad at all, provided it’s appropriate to the relationship ( don’t compliment a married woman if it could be confused with flirting for example).
Just been my experiences and .02, best regards.
Edit: apologies in the second paragraph I was referencing the workplace nit just regular situations, just to clarify