At the moment I wear birkies (Madrid style) on warm days and rocket dog brown suede 'trainers' on colder days. In the winter I wore timberland boots with them.
On the top - in winter I had a uniform of v-neck fitted jumpers with white or brown vest underneath.
In summer - vest tops, shirts, t-shirts. Just the usual straight forward stuff.
I don't wear them for nights out - I wear dark, fitted ones that look smarter although Madonna wears boyfriend ones with heels to go out in! Have seen pics!