The other day I was riding down in the elevator at my office and it was just me and one other person. She turned to me and asked, "do you think I'm dressed ok for an interview?" I thought maybe she was on her way to an interview, but anyway, she was, in my opinion, dressed fine*, so I said so. At that point, she told me that she'd just been on an interview and the interviewer had told her she wasn't dressed well for it. I was sort of in surprised and reassured her that she looked ok to me. As we chatted, I figured out which company in the building she'd been to and thought, hmmmm... they certainly don't dress any more formally than what she was wearing, and some dress much more casually.
I felt bad for her and wished her good luck in the end. Afterward I thought about what I would have/should have said if in fact I felt her clothes were inappropriate. Fortunately this wasn't the case, but would it have been prudent to give her constructive criticism if I felt she needed it? Is it rude to tell someone what you really think in this kind of situation, or is it ruder to hold back when you've been asked for your opinion?
As an aside, it also made me wonder about the interviewer and whether she really believed that or not, or anyway, what her motivation would be in saying it.
*She was wearing dark slacks with a dark plain top and a knitted short vest over it and sandal type shoes with a medium heel. So nothing outstanding but well within the realm of "business casual".