Always. Women have a hard enough life as it is, if I have any reason to compliment one because of looks, hair, outfit, whatever, I will no matter what. Life is too short not to grant compliments to women.
I like your style. My Dad used to say "treat every woman you met like she is the most beautiful you have ever seen and your life will be soooo much better for it!" Yes, even the 2's and 3's.
I am on the fence. I will often outside of work' tell the checker she has a pretty name, tell the waitress I like her ink, stuff like that. But at work, esp the last few years, its almost never.
Was not a conscious decision but it sure has happened. None of that in the office. People take stuff wrong and out of context.