Early March will be my first trip to Italy, and I hope to travel light without checked bags, which means choosing one pair of shoes: comfortable, but smooth-soled, leather shoes, or even more comfortable and versatile rain-proof gray cross-trainers. This is an economy trip that would not include formal cultural or dining events, but.. would anything other than leather footwear be an aesthetic error that would somehow diminish one's personal experience or success interacting with Italians on daily logistical matters?
This comment from the Etiquette section is quite firm: "it's not sensible shoes that are not in fashion in Europe, it's that ugly sneakers make you stick out everywhere." (Somewhat like a response in the topic about asking for water in a restaurant: it's tacky).
On the other hand, the local folks anywhere aren't subjecting themselves to consecutive long days of curiosity on foot, in unpredictable weather, exploring sights, streets, trails.