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Men from older generations were taught to always compliment a women, they were just never taught how to properly do that. As a Gen X women I was taught to appreciate the attention. It was all weird and wrong. Bad behavior is not excused by past experience
It does sound like he is trying to be kind while learning to navigate the new office culture. I (as a women) often compliment others by their jewelry, color choices, shoes, new hair style, or whatever; but it doesn’t come off creepy because I am not a man. If he is being respectful and not crossing any boundaries (along with recogning your accomplishments and hard work) I would just go with the flow. However, if it is making you feel really uncomfortable, it is something that you need to address with HR. Trust your gut.
To me that's totally fine as long as YOU don't feel uncomfortable by it. If it's not bothering you, I would just keep doing what you're doing.
It’s definitely about perspective on some level. Remember seeing something about complimenting people on outfits is appropriate, and tends to win people over because unlike a lot of things it’s well within their control. They took the time to put it together thoughtfully, so taking notice (not in a creeper way), can be well received when trying to connect with people. Maybe that’s what he’s going for?
It's a neutral area. He likes you to some degree, but 99% of men would not do or say anything at work that would get us in trouble. So it will always remain compliments.
I think he’s trying to be nice. It’s tough to see from the same angle at different ages, life stages, etc. Sorry you are in this position though.