Hello, what is the weather like in Italy in October? Is it sandal weather, closed-toe shoe weather or even boots weather? Thanks.
Shoulder season is unpredictable until you're only about 5 days out. Even then, precipitation forecasts aren't terribly reliable. My priority is comfort and stability. No matter what the weather, I wear lace-up walking shoes. The only question is whether I anticipate so much rain that I decide something waterproof is a good idea. I don own boots, so I can't comment on that option.
Standard (lightweight, thin-soled) sandals would be a very bad idea. The won't give the soles of your feet adequate protection from full days on hard pavement. They also are problematic on cobblestones.
I wear sandals as much as possible. Weather in most of Italy in October is likely to be sandal-friendly, but sturdy ones with thick soles for all the uneven surfaces. If you get a little rain, those surfaces can also be quite slick.
I took 3 pairs to Italy in late September--black ankle boots, black Skechers, and tan leather Teva sandals. This was the perfect combination for me. I was grateful for the support of the boots when exploring Pompeii, the coliseum, and numerous walking tours. A set of gel insoles made the Tevas more comfortable for extended wear. I'm a flip flop girl here in Texas, but I would not suggest flip flops or beach-type sandals for touring. Enjoy your trip!