Compliments

So because I'm neurotic and weird sometimes I get worried when complimenting people. I guess I should specify I mean more acquaintances. I can compliment friends with no problem. Like I wonder if they'll take it the wrong way or they'll think I've got hidden meaning behind something I say. For example, a male student worker (not ours but one I'm friendly with) has a nice smile and I thought of telling him so. But then my next thought would be, but would that be weird? The other day someone from Financial Aid wore an outfit that looked great on her. I wanted to tell her I thought so but then worried it would be odd. The only one I've managed to squeak out recently is to someone who has lost a lot of weight (through hard work and almost a year on Weight Watchers not due to terrible illness or anything scary). I did manage to tell her she looks smashing, because she does. But even then I second guessed it before I said it. Hmmm... I am going to have to work on that because I'd like to be the kind of person who can give a compliment and mean it and not sound smarmy or stupid.