Shoes for Italy

I have been on the prowl for comfortable yet cool (both temperature-wise and style-wise if possible) shoes to wear on our trip to Italy. After many recommendations from folks who have travelled to Europe before I made a few online orders and have settled on two out of the 3-4 pairs that I plan to bring.

1) Fit Flops

These are the most comfortable sandals I have ever slipped on and I already broke them in both wearing them around the house and outdoors this weekend taking my parents around downtown Chicago. But really, I don't think there is much of a break-in period for these because they fit very well and have given me no cause for concern. I got them in bronze/pink so that they would look less orthopedic and they are pretty cute. Feel like I'm walking on a cloud, yet supportive and I think they will remain supportive even on uneven surfaces.

2) Keen Amsterdam

I had been told the keen was a nice comfort/sport brand and I liked the look of these shoes online so I gave them a try. I got them in the Rust color and they fit great, feel very comfortable and I also think they'll give a nice pop or color to my casual site-seeing gear. I plan to start wearing these on my walk to work in the mornings to start breaking them in, too.

I've also had a few failures.

I really loved these Converse All Star Slip-ons, but they ran too big and the next size down was too small, so it seems I am between sizes. :

I also tried Clark's Privo Mesa shoes, but they slipped off of my foot too easily:

I hope to find one or two more pairs, one converse like shoe and maybe one a little dressier sandal or mary jane that I could wear with a skirt or dress to dinner without having a skinny heel that I'll be dying to take off. Anyone have any other ideas for a tennis shoe/sneaker brand that isn't the normal, white cross trainer type AND a dressier comfort sandal or shoe for nicer dinners?