I feel like I have to jump in here because I think my office tops them all. As a man, I really could care less what people wear but I'm telling you its bad. We have one guy that habitually tucks his dress shirt into his underwear so that about 3 inches of it rides above his waistline. When he bends over, the women in the office run and hide cause his hind parts are clearly visible.
My boss, though I admire his thriftiness, crosses over the line himself. He has not bought new dress/work clothes, I swear in at least 20 years. He showed me his wedding picture from 22 years ago and the tie he had on in the picture is the tie he wears today, twice a week. He is proud of the fact that he never wears t-shirts. This makes his nipples clearly visible through his worn out shirts. This has also created terrible looking brown stains in the armpits. One pair of pants he wears are pink with an elastic waistband.
The office secretary just turned 81 at the beginning of August. No fashion faux pas here, she just has a flatulence problem that she is in total denial about. When she walks across the office, she breaks wind the entire way.
I have so many stories. I swear sometimes I work in the funny farm.