With sandals or other open-toe shoes, never. If it's cold I may wear them under slacks or with a dress; If I do, I always wear enclosed shoes. With dresses, I buy good quality hose that are thin and very neutral beige to be transparent on the legs. Quality and good fit are crucial (I wear them so infrequently the cost doesn't unreasonably add up). Cheap hose don't fit well and look awful.
Easy Spirit Traveltime clogs. You can get them with a backstrap if you need/like one. Tip for these or any shoe with removable insoles: Take out the insole and cover it with a low-cut athletic sock, the foot part on top of the insole and opening underneath. Put the now-covered insole back into the shoe and you now have the comfort and absorption factor of wearing socks without "wearing" socks. Easily changed for laundry purposes and protects your shoes from the sweat factor.
I rarely buy form-fitting clothes any more so I don't often need to use shapewear and when I do it is very light (just enough to give a smooth line). I'm a comfort person and believe that no one looks their best if they are hurting. I'm sure many people can wear shapewear comfortably, but I've never had much tolerance for it.
When I have a prepaid package, I take a stack of ones and give them out as warranted - not for every drink, but if they provide extra attention, they come to me rather than me going to the bar, they also bring a water, etc.