Have you seen Stacy London's (from What Not to Wear) work with State of Menopause? She's selling skin products, but more importantly - she's using her influence to open up this conversation. She talks a lot about the invisibility of women "of a certain age."
Here in Austin, we've had the right to be scruffy at all ages. I find that unflinching eye contact with others is what gets me seen - and not run into! Jeez! My projection of visibility by believing in my right to be seen is what seems to make others see, and speak to me.
Or maybe the only places I usually go are my little grocery coop, my gym, and my office. Or the bike trails.
Yes. We can have both. Comfort and visibility. Style be damned!