If you haven't warmed them up a bit first, it never feels right to compliment what they wear.
On the other hand, people love hearing that they have a nice playlist or run a cool place. It's something we put a lot of us into, so being complimented about it always hits hard.
Compliments are an acquired skill, but one that's so satisfying to use.
"I love that sweater" [that you chose] is a lot friendlier IMO than "you look great in that sweater"
I also try to indicate with my tone and bearing that a response is not expected, a good compliment is a gift (IMO) and gifts are freely given without expectation of payback.
I also like to stick to commentary I feel i actually know anything about, i wear earrings, so often comment about them. I dont wear makeup, so i rarely go there. I think fancy shoes are fun, etc.
Yes! This so much this!
In NZ the culture is a lot more earnest, so it’s a bit easier.
* Is that the new model of X? They say it's great.
* Where did you find Y? I've been searching for it a long time.
* Do that Z work so well as they say?
My only actual skill: being fine with awkwardness. It happens 20% of the time