Good Afternoon –
I just read your post and thought I would respond. I know how tricky packing can be - especially when you are trying to plan for a range of temperatures while saving space for souvenirs!!
To give you a better idea about the weather in Rome in October --
Average temperatures range from a low of 60 degrees to a high of 72 degrees.
If you are comfortable wearing sandals in those temperatures then I would suggest packing a sandal that is sturdy and offers good foot/ankle support. The roads in Rome are often "paved" with uneven cobblestones – and there are some days when you do spend quite a lot of time on your feet - so it’s a good idea to make sure that you are comfortable in whatever you end up wearing. Picking the right footwear is very important to the health happiness of your on tour experience!
In regards to your questions about shorts -- Italians in general tend to be a little dressier than most North Americans – so I would suggest that you bring a pair of slacks for the evenings and for dinners.
During the day you should feel completely comfortable walking around in shorts. One suggestion that might be a good option for you is to look into purchasing travel pants that have pant legs which zip off at the knee so that you can convert them to shorts should you get too warm. It’s a great way to minimize packing space and get two outfits out of one piece of clothing!
Please let me know if you have any other questions
Best,
Emily