Summer
Winter (Tango gambell is teh closest although no heels)
On summer I usually have two types of shoes, ones for casual/work/city/drinking. Need to be comfortable. The other ones are more robust, mostly used when I'm doing something stupid or working outside. The robust ones I've used are the shoes I got from my summer job some years ago. A bit heavy (some steel padding, good for kicking stuff) but quite comfortable as well. And no need to watch out for making them dirty or anything. And naturally the winter shoes need to have some padding to make them more warm than the summer ones although not much. Some tread for slippery surfaces is a requirement too. For normal outages I have some cheapo sneakers.
Few years ago I had winter shoes that had thick base which made the shoes first off quite heavy but the thickness made driving a car a bit tricky as I couldn't feel the pedals at all. The main annoyance with the shoes was that they weren't very comfortable. Everytime I had to walk more than a mile my feet started to ache.