I do believe not dressing old. I don't mean to offend people, but I won't step into Chico, or any place that sells elastic pants (especially jeans). I'll buy jeans with stretchy material, but not elastic waist.
About 4 or 5 years ago, my parent's got me a gift certificate for Chicos for Christmas. My D still laughs thinking about my facial expressions when we went to shop there. This was an attempt by my mother to make me "grown-up." She also wants me to cut my hair short, but that is another subject. It took me three trips to Chicos to use up the gift certificate, and a good portion of it was on some jewelry.
I would never wear anything but heels with jeans. As we get older (not me of course) I think giving ourselves the appearance of long lines becomes more important to balance out a few "problem" areas. I think a dark washed jean with pointy toed heels with just a touch of toe cleavage, a white shirt and some type of jacket can take you just about anywhere, be age appropriate, yet still modern and fresh.
I shudder thinking about my favorite grey stirrup pants with oversize cowl neck sweaters that I used to wear in the 80's. Never again.