In Europe, I tend to "dress up" a bit, which for me is a skirt and sandals or boots. I might get by with jeans during the day, but I try to wear something a little nicer for dinner to blend in a bit better with the locals. I always took it as a good sign that I was often mistaken for a native when I traveled alone. No heels though; I can't walk more than a few blocks in heels.

Most of my North American travels revolve around the outdoors, so I keep it low maintenance. I might still wear a casual skirt for dinner, but I do absolutely nothing to my hair (which is a real vacation for me since my hair takes some work). I enjoy wearing a bit of makeup unless I'm working out or hiking/biking.