We're planning a trip to Belgium, and then either Paris or London, this October (15th through the 25th).
When the weather gets cooler here in Virginia I switch over to my trusty Woolrich Yankee boots with Horween leather, and Vibram outsole. They are very broken in, with a small heel, and I've found them to be a great cross between a hiking boot and a loafer. They are super comfortable, and also go well with casual or a bit of a nicer outfit.
During summer, I often wear my Sanuk Pickpockets. They are crazy light, pretty much like a sandal, but they look nice enough that I can wear them to the office or to let my dog out in the morning. I like the 'Pickpocket' concept, where you can tuck a small amount of cash, or ID, credit cards etc. in their little pocket on the top of your foot.
My Converse Chucks are my alternate shoes (I'm wearing them right now in the office, but also like to wear them in a variety of different contexts). They are actually recommended by people who recognize the benefit of having a comfortable shoe without a heel (yes, running shoes have a heel!). Allowing your foot to remain flat, they mitigate issues related to the shortening of your Achilles Tendon, and allow for greater flexibility and mobility (i.e. greater comfort when out and about being active).
I would like to wear one pair of shoes and pack another, and I'm trying to decide which combo would be best suited for me. The lightest, easiest combo would be wearing the Chucks most days, and then using the Sanuks as house shoes, as well as for any nicer meal we might go out for (by nice, I don't mean suit and tie type places, but I definitely would appreciate insight in that area!). The most stylish combo would probably be the Yankees with the Sanuks, and the added benefit would be that the Yankees have a Vibram outsole, and are good for shock absorption and keeping my feet dry and therefore warm (but they're unlined, so they don't tend to overheat me either).
I can offer up any more info, and greatly appreciate your thoughts. One thing, I do own running shoes, and while I could see these being a comfortable option, I really don't want to be "that guy!" Thanks, y'all!! :-)