I finally broke down and spent more than $50 on a pair of walking shoes about 15 years ago.
Living in New York, and doing a lot of walking while traveling, I found Ecco black leather slip ons to be worth every cent. I put a lot of miles on my first pair in 10 years. They’re still usable for walking the dog, but they’re pretty beaten up now.
My second pair, Ecco Helsinki slip-ons, have not disappointed me in the past 5 years, either. They’ve been to Europe, Canada and Mexico and look great with jeans, dressier evening wear, or even a suit. I get them professionally polished when I have time to kill at the airport. There hasn’t been a broken seam or a split sole yet.
Caroline Morse Teel certainly has more fashion sense than I possess, and has written about the shoes you might want to consider for a trip to Europe in Smarter Travel. Most of them are women’s shoes, but there are few in there for men, too.