"Well, I mean you wouldn't buy a skirt without
asking your friends first if it looks good on you."
We live in an increasingly casual world. More and more work places require less and less professionalism with your attire. I have seen people show up to work wearing cut off t-shirts, yoga pants, and very ill fitting clothes. No I am not talking about young cute out of college mistakes, these are grown ass adults in a professional office.
It sounds like a cliché, but you really do need to dress for the job you want...at the very least dress for the job you have! With Facebook and other social media, you already have enough going against you in the fight to be taken seriously. Don't make it any harder on yourself. How you dress and how you carry yourself also shows people how you expect to be treated.