Good question Wes....
I guess for me it's a function of being a *cough* mature woman but once I passed 40 I gave myself a gift. I tossed out that damn bathroom weigh scale, I retired my makeup bag to the status of "when I bloody well feel like it", tossed the evil and uncomfortable wire bras to the back of my drawer and decided that being me wasn't all that bad a thing to be.
We all struggle with what society expects us to look like but I think especially older females get the worst of that. At some point for me anyways, I decided that what is in a person's soul, their eyes and their actions is worth a lot more than what good makeup or genetics gave them. It's a very freeing experience and likely one of the nicest benefits of getting older.
On the shallow side, I did think when I saw this lady that someone aught to tell her to not wear dark nylons with light shoes (me being such a fashion plate myself and all that LOL).