The consumate traveler will be very familiar with the dilemma they face regarding style versus functionality of good travel shoes... they, in fact, are mutually exclusive traits. Comfortable, good walking shoes are just downright ugly. But, in the same breath, you have to be completely lacking self-awareness to have the sort of disconnect that allows you to have no self-respect while traveling by allowing yourself to look awful in an overly-cautious-tourist sort of way, which also makes you a giant target for all sorts of ills (no native would go around dressed like that). Hello!? It's still YOUR life, whether it's lived at your permanent address or from a hotel so have some dignity and keep it together wherever you are.
Although, I'll admit, easier said then done when it come to footwear that's meant to be used for walking. Taxi shoes are not an option on a global trek. And you won't find anything cheap that really, truly will leave you sans blisters, aches and ingrown toenails at the end of a trip unless you eBay it or wait for a super duper clearance sale (and even then, you'll be shelling out at least $30 to $50 for the ugliest of the lot). You get what you pay for, people, as with everything in life.
Which brings me to the design feat that is NAOT shoes and sandals. It's an Israeli brand that seems to be making the very best of a hard situation -- mainly making stylish (as much as is possible) yet insanely comfortable, serious walking shoes and sandals. I opted for the Kayla in copper. It might look like a Birkenstock in the image but it looks only marginally like that brand when you see it live. Yes, they are still slightly orthopedic, but I refuse to walk 5 continents in ballet flats. Not this time. I will sacrifice a bit of style for a ton of comfort and, actually, if you think about it, the heel on these sandals makes your legs and dresses look better than flats do so there's not really much lost in the style stakes, is there?
Hanig's Chicago has an amazing selection of 'stylish' orthopaedic shoes like Thierry Rabotins (out of my price range), Kenneth Cole Reaction, NAOT, Dansko, Keen, MBT, Fitflops, Ecco, Söfft, Taryn Rose, Tsubo and Think!. That's where I bought the NAOTs and I have a feeling it'll be one of the best purchases I made for this trip (along with a fabulous Diesel top, DEET insect repellent and a Netbook).