I bought a pair shoes I probably will wear to Italy (unless somebody convinces me that I am more likely to get robbed or attacked wearing them versus something else): nike brand shoes, mostly black suede, white nike swoosh, white soles. Dress shoes would be excessive or overkill. Hiking shoes may be excessive too: I tried some on but they have a tread that is supposed to provide good traction on unpaved trails or ground, but hard paved surfaces will just make the tread wear out too fast. I tried on a certain pair of Ecco brand shoes at a store called the walking company, with a certain kind of insole (aka "orthotic"): they fit perfectly, and technically this is what I "need" because my feet are flatter than the average person's feet, and I normally do a sort of gait called supination where all my weight goes along the outer edges of my feet when I walk, but I was bothered by the unfamiliar sensation of the insole against the bottom of my feet, that the salesman put in the shoe; I am not used to this level of support, and I was afraid that I wouldn't get used to the sensation.
Clothes I own that I plan to walk around in, in Italy (unless somebody convinces me otherwise) include:
blue khaki pants and/or a sort of lightweight pants I bought before my last trip, which have two inconspicuously located zippered pockets, an unzipered pocket on one side, in additional to the typical two front and two rear pockets found on most mens pants, and slots to provide ventilation,
2 or 3 button down long sleeve shirts, without brand logos, that I think are reasonably lightweight, made of cotton and polyesther, I wear untucked
a sun hat with a smallish colombia logo,
The kind of sun glasses that cost under $25 and fit over my perscription glasses.