For cool weather travel, my Mephisto oxfords can't be beat! I wore them two weeks straight in China last fall, and they were super comfortable (from day 1 -- no break-in period was needed) and cute, in black with shiny toes and heels. I hiked up Yellow Mountain in them, and wore them in the cities of Nanjing, Guilin and Shanghai. They were kind of expensive, but worth it. I never had sore feet, legs or back, and always felt stable.
In the summer, I wear my Taos sandals all day every day when traveling, super comfortable, cute. I always get a sturdy sole, adjustable top straps, and must have ankle straps so they won't fall off at an inopportune moment. My Taos have carried me through Istanbul, Ephesus, the Greek islands, Venice, Rome and more. I also like my Mephisto fisherman sandals to go with pants. I wore mine to visit the pyramids in Egypt, climb the Acropolis, and wander the ruins of Ephesus. I pack light, just one carry-on size bag plus a small airplane bag, so I wear one pair and take a dressier pair of sandals for evenings, and some kind of compact running shoes.
Good luck on your search. I am always on the lookout for the perfect travel footwear!