Q: I'm about to take my first vacation to Italy. What's a stylish shoe that's also comfortable for hours of sightseeing?
A: I'm envious—can I go with you? When traveling abroad, my motto is dress to fit in. Gym sneakers scream "tourist!" Besides museums and markets, you're going to be stopping at restaurants and boutiques, where overly casual shoes can look tacky.
Many of Rockport's styles, including several in the new spring collection, have Adidas technology that cushions feet with foam and rubberlike padding. Two pairs—one heeled, one flat—are all you'll need. I've arranged an exclusive discount on women's shoes at Rockport.com with code OPRAH through July 16.