I went to Europe this June and had a hard time finding fashionable walking shoes. Several travel blogs suggested I purchased a pair of Superga Cotu Classics so I did. After a few wears, I didn't feel they'd be quite comfortable enough. Plus, my feet swell a lot when I walk so I didn't want anything that covered my toes. I considered bringing my white and hot pink trusty running shoes since they are sized for swelling (Brooks Glycerin 9) but I thought they would scream "Hi, I'm American!" I also own a pair of black Birkenstock Gizehs but I didn't have the chance to break them in on time. For me, it takes a while to break in my Birkenstocks.
I ended up buying a pair of Born Saffron gladiator style sandals. They were actually pretty comfortable for a few miles. I also thought they were cute for a comfort shoe. However, we walked a lot (about 3 to 5 miles a day). The Borns didn't cut it as the soles are not very thick and there isn't much arch support. The balls of my feet hurt and I ended up buying a pair of Clarks Active Air Sandals while I was in Madrid. I bought the Robe Neon style. It's a little bulkier than I would liked but it felt like I was walking on little pillows. They are ultra-cushioned and the style makes it easy to adjust the tightness around my foot in different locations. Now that I am back, I'm not sure how often I'll wear them (maybe to Disneyland?). But I am so glad I had them in Spain! Unfortunately I don't think they offer the Active Air style in the U.S. although there are a lot of other cute Clarks styles. I ended up alternating the two sandals, using the Clarks when I knew we'd be doing a lot of walking.