I have tried traveling with quite a few pairs of shoes over the years — everything from Doc Marten boots, to Converse All Stars, to Asics running shoes, to expensive ballet flats of various brands. In a good travel shoe I want support, comfort and flexibility. They have to go with everything in the limited but multi-purpose wardrobe I bring with me. And they have to not give me blisters.
I have failed at this a number of times. The ballet flats, which looked so comfortable and supple, were a particular nightmare. I had bought them tight enough so they wouldn’t fall off, and apparently, this was a bad idea. More than once, I hobbled back to my room and taped up my feet after wearing them. Just like real ballet shoes!
The Doc Marten boots, and even the Doc Marten shoes, were heavy and really not that comfortable. The boots even did this weird thing to my toes.
The Converse made my feet stink and were not good for walking, not even with some foam inserts. The Asics were comfortable, but they were also relatively hideous. I have photos of myself from France in a black peacoat and those shoes. The shoes really ruin the look.
In essence, what you want is a shoe that fits without moving too much, but also without pinching in any way. It needs to support your feet comfortably, allow them to breathe if necessary, and either keep them dry or allow them to dry quickly, depending on the climate. And the shoes need to look good and not label you a tourist. Even if you think you have found such a shoe, take it on a long walk anyway and see how you get along. If, even after breaking it in, it doesn’t feel good, do not assume your relationship will improve upon exclusivity. And do not try to combine breaking it in and exclusivity.
Here are my all-time favorite traveling shoes. From the left: black Chacos, which I have gone hiking and even running in, and have also worn to conferences with long pants. You adjust them to your feet and they stay put marvelously. Cost: about $90 new. So far, they’ve lasted through six years of heavy to moderate use. Although they really need new soles about now. Next: North Face flip-flops. I bought them a bit small, for $10 on sale, and they are the most comfortable flip-flops I’ve ever owned. Because they stick on my feet pretty well, they don’t give me blisters. I can wear them with almost anything. Next: Hush Puppy Mary Janes with rubber soles. I got them for about $30 secondhand, and I’ve done everything from light hiking to heavy dancing in these puppies (sorry, I had to). Last: Black leather boots, unlined. Especially good for a trip to Germany and Scandinavia. $50 on ebay. They could also use new soles at this point.
Botkin Creative 
Love the chacos 🙂 I’ve even worn them backpacking with wool socks when I left my hiking boots at home. When I’m traveling light I’ll often take chacos and cowboy boots – the chacos go everywhere except to a nice restaurant, and the boots I can dress up or down as I please.
Chacos! I walked into REI about 12 years back, told them I had plantar fasciitis, and what could they do for me. Chacos! They have been all around England twice, through Turkey, Greece, Italy and France, to the Grand Canyon and back, and across Canada by train and through several Oregon Country Fairs. Yes. I wear them with socks when appropriate. I had one alternate pair of Keen’s – almost as good, but even though about 7 years newer, they popped their fastening loops this summer. The Chacos are still with me.
Natalie, I’ve also done that trick with the wool socks. I flattened the toe loop and it worked just fine. Normally there’s no way I would spend $90 on a pair of sandals, but in this case, it was totally, completely worth it.