my rule rule of thumb:
unless it's lounging around the house, doing yardwork, or going to a sporting event
ALWAYS wear what a chick tells you. Last fall I went out with a friend of mine as she needed something at the mall, and I needed a new "bar" shirt (you know those stripped dress shirts, but with no pocket, yeah generic I know) - so we went to Le Chateau (which I thought sold exclusively women's clothing) I swollowed my pride and bought two shirts.
I was iffy wearing them at first, until it seemed like every girl I knew commented on them. If a chick says "pink shirt" you get a pink shirt, if she says shorts sleeve dress shirt (as much as I hate them too) you get a short sleeve dress shirt.
Let's face it, guys = ZERO fashion sense (why the ones that do have it get a TV show)
Same way that chicks don't know guy stuff like how to fart and belch at the same time.