When in doubt, go with loafers. Like this sleek (and comfy) pair complete with a chic keeper ornament.
Journey
Loafer$135
You've selected Journey in Light Grey size
Ultra FlexThis style is made with Ultra Flex, offering a soft upper and 360° movement outsole for total flexibility.
Pillow WalkDesigned with dual density foam and padded insoles, this style is extra comfortable.