It's definitely a double edged sword to always try to mimic your boss' preferences. Sure it's good to take note and not be intentionally defiant, but I'd be worried about coming off as a pushover. It gives the impression that you have no originality or mind of your own--which I guess is an asset in some fields, unfortunately, but definitely a liability in others.
I am not saying that you fall into this category--just musing on what a fine and tricky balance it is. There is merit to both sides.
Sometimes if I know someone has a predilection for certain outfits or pieces I wear, I will try to wear them more often around that person. One of my friends likes mod-ish looks, so I tend to consider that when we hang out. The dress I am wearing today got a lot of positive comments, so I'll probably wear it to work more often. I like these outfits as much as the complimenters do, so I'm happy to sport them more often.
But one thing I never do is to NOT wear something because someone doesn't like it or has some weird psychological block against it. So no, I don't avoid certain things around my critics.
I sometimes get flack for my color choices, especially yellow and gray, but I still wear them regardless of who's looking. Color is so subjective, no matter what the "experts" say. So is style, for that matter. I don't pretend that I can please everyone, nor do I particularly care if I do.