Hi Jamie, Women compliment other women on their appearance or outfits all the time. I have gotten to where I act more like a woman when I'm out (dressed or not) and one thing I do now that I didn't used to do as much is compliment any lady I see out that is well dressed. My wife has always done that and so has my Mom, women do those things so nothing wrong with paying a compliment. I would never ask if they was male that would not be a good thing to do, no one wants to be outed. But I have had a couple of ladies make comments just in passing by about how I'm dressed if I did a good job that day.