Do you tell a friend they are not fashionable, or do you not say anything?

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How many of us have a friend (or more than one) that are wonderful people, but who wear i.e. pleated pants with peg legs from the early 90s, or a sweatpant outfit that has bands around the botom and you look like a giant marshmellow??? Just a few examples. I have a dear friend who is very out of date and would love to help her, but I feel that if I say something it would sound, and be, cruel. I've tried to take her shopping but she doesn't like shopping. What other ideas can I subtly make? Or do I just leave it alone? I don't want to be meddlesome, but it affects her personal and professional life. I think she'd be taken more seriously if she dressed more apppropriately.