traveling to Italy kahki shorts

I vote yes. Wear whatever you like :)

What are the chances you will run into Rick? Wear what you feel comfortable in.

khaki shorts, yes. Flowered shorts (particularly for a guy), no. For years I wouldn't wear shorts in Europe due to Rick's disapproval. Then in 2002, it was very hot, and I saw German men wearing them in the Alps, so I bought a pair and wore them. Then in 2009, it was hot in Munich and men were wearing shorts, so I wore the pair I had brought along as pajamas. BTW, here in Denver, I wear Khaki short almost every day, when it's too hot for jeans.

Yes to wear both.

Just as in the US, it depends on what you are planning. Do you have a job interview? You wouldn't wear shorts to that but that's probably not what you are planning. You're on vacation so you can pretty much wear what you want. I personally only wear shorts for the beach or a hike and wear long pants the rest of the time. My wife wears a skirt, capris or shorts almost exclusively. Some Italian churches are strict on covered knees and shoulders. If you plan to visit a church (or go to a nice restaurant), shorts are probably a bad choice.

I agree with Brad, it depends on what you are doing. If we have a day of museums and churches planned, then I'd wear pants. If I'm hiking or going to the beach, I'd wear shorts. I usually toss in a light weight pair of hiking pants with the zip off legs so I'm prepared for either need. I have noticed more European men wearing shorts but usually just in resort areas or more rural tourist destinations--not so much in the larger cities.

Nobody cares, be comfortable. Rick's suggestion is out of date. My wife works in fashion and said it's all the same clothing we have here and worn pretty much the same. People often confuse how folks dress in big cities from more rural areas.

Yes for both shorts and capri's. Weather in Italy mid-sept can still be warm and whenever in europe I try to be as comfortable as possible. When I was in Paris and Switzerland in june there were a lot of tourists and locals wearing shorts as the temps in Paris were >80 degrees. In Switzerland shorts came in handy in Montreux,Luzern, and Lugano.

A vote yes also for shorts and capris. Wear whatever is comfortable for you. Jeans are okay too. Just be mindful of proper coverage of shoulders and knees for churches.