After a career spend in front of people who are constantly making comments about my appearance and what I wear, I regard these comments as just observations, nothing more.
Trying to interpret underlying messages just leads to my feeling self-conscious about my choices and suspicious of others' intentions. And feeling suspicious and self-conscious is a deadly cocktail that makes me want to retaliate by throwing a negative evaluation back along the lines of "well, look at how you've chosen to dress" and spend my time ascribing motives and intentions to others that may or, more likely may not, be accurate.
We all make observations about what others are wearing all the time. And, mostly, our intention is neither to hurt nor to compliment; we are just verbalizing our observations about how we are alike, or different, in our choices. And, even if the commenter is trying to bolster herself by a negative evaluation of my outfit, the comment usually has more to do with her need to validate her choices by putting down mine. Random criticisms and compliments usually say more about the person making the comment than the target.
You can't have a career that puts you in the spotlight everyday without developing a bit of a thick skin. If my husband, my friends, and my mirror tells me I look good, that is enough for me..