I remember the first time one of my best friend's went shopping with me. She took one look at me and said "it's awful, take it off" I was floored! But once I got over it, she was the first person I called for an opinion or advice.
I guess it just depends on the person. I'm a firm believer in if you don't have something nice to say, don't say anything at all, but if I ask, I want the truth.