If they fit your feet correctly, Dansko clogs, beloved by many restaurant workers, nurses, and others who spend most of their work day on their feet, are awesome. I've happily used my pair as travel and airport shoes for years. (I'm a she, and my clogs also are an oddball leopard print that actually gets compliments from airport security workers when I've had to take them off.)

I also love my Ecco loafers but they aren't waterproof, though some of the Eccos are.