When I first started working here at the ag. extension office, everybody dressed down. One co-worker in particular was showing up to work wearing shorts and flip flops. I just can't dress that way--not even in the privacy of my own home--unless I'm washing the car or something. I decided to wear nice slacks (I guess the younger gals call them trousers, although I think of trousers as men's pants), nice tops, etc. I'm not trying to get promoted or climb up the ladder. I'm just working for retirement $. Still, I have a high degree of self respect, and I want to project a good image. Next thing I knew, that co-worker was no longer wearing shorts and flip-flops, and when my boss gave me my first evaluation, he remarked that I had "added a new professionalism to the office." So YES, dressing well pays off.
On the flip side, I don't admire people who wear expensive clothing that makes you wonder how they can afford to do so. I'm sure most of us have some expensive items we received as gifts or saved up to buy, but when I see someone who consistently wears expensive clothing and doesn't have the type of job/occupation that would support it, I can't help but think that person doesn't have the self discipline to live within his/her means. Also, I think that if you overdress for work, you're employer might wonder if you're getting paid too much. I don't know if that's true or not, but I don't wear my higher-priced garments or accessories to work.