Best: Shoes
You know you're going to have to take them off at the security checkpoint, and unless it's negative-something degrees outside, we suggest wearing comfortable flats that can slip on and off. Don't forget to bring fuzzy socks on the plane with you, it gets cold.
Clockwise: Jeffrey Campbell, $145 ; Veeshoo, $150 ; Joshua Sanders, $440 ; Stella McCartney, $600 ; Manebi, $130