Dress shoes look great, but mine aren't even in the same dimension of comfort as the ugly/klunky/cheap rubber shoes. Is that one reason they sell 1 billion pairs of Ecco/Sketchers..? In my limited experience, comfort is inversely proportional to price. (I can't speak for costly handmade shoes) My "new" $500 Saks/Florshiem shells. They are sturdy, but so are cinder blocks. It's like ice skating in sheet metal boxes. I'm afraid to wear them out of the house, frankly. My $300 Barney's, A&E saddles, etc. Feet killing me after 3 hours. Inner soles like rock. My $100 J&M? Average. Lots of padding inside. Thankfully. My $30 Bass "clogs"? Massive rubber soles = soft like a dream. These are what I wear to work. Daily. I could run a marathon in them. They're not sleek/stylish, but I want the comfort/utility. It it worth noting that I wear the cheap shoes about 20x more than the fancy ones, so the former are much more broken in. That certainly could be the difference. If I'm shipwrecked on an island, and there is no party to attend, I'll be begging for a pair of Ecco/Lug Sole/Uggs/Rubber sole/hikers/whatever to get me around. What's been your experience?