This is a complex issue. It reminds me of a friend whose mother said to him that she didn't care if he was gay, she just wanted him to stop "acting so gay". There's a certain component to that in our society with regard to aging; in other words, it's okay to be old as long as you don't look old.
I think true female empowerment would mean that every woman could look and be the way she wants without being judged unreasonably. It is my choice to work on my external appearance, but for those without the time, energy, motivation, or interest, who cares? As long as someone is clean and appropriate, it's not my place to decide what they should do.
I only recently realized women were "supposed" to cut their hair after a certain age in this culture. I try to see a person, not a "50-something year old with the wrong hairstyle for her age group". Self-improvement is a luxury to some extent, and although everyone can make an effort at any price point, it's certainly fine with me if they don't.
Here;s a photo of Susan Butcher, who won the Iditarod several times and died a few years back. She was an incredible athlete, among other things - and yeah, she could have done a better job with her hair, but that would not have been "her". This is a very typical look for Alaskan women - for better or worse...
http://www.iditarod.com/learn/butcheralbum.html