I like the ballet flats, as I think the key to better-looking ballet's is a bit of a true heel, sturdier construction (not dowdy-heavy) and very slightly ovalish toe. The wedges look great so if they're comfortable that's a plus--I feel stable in wedges, but can't tolerate the pressure from the heel height for all-day wear, still.
The other thing in sticking to your comfort guns is to keep gravitating toward those styles that are more inherently comfortable--Angie's post today--loafers, boots--and find some that look sharp and modern, and build some outfits around them. The holy Grail for me is some kind of summer bootie that works with skirts, as usually they are feet-friendly.
