Ok, maybe loafers, if I was in a casual mood. For yard work and picnics I wore Sperry Top-Siders, (basically cloth oxfords).
It was our first trip to Manhattan that broke my resistance. My leather soled shoes were not up to long walks on city sidewalks. I vowed to return with some serious walking shoes. The next year, I equipped myself with a formidable pair of black Merrell Pulses.
They did the job. I walked for miles, uptown, downtown, and I had happy feet. But they were so massive and ugly. I was embarrassed to enter a nice restaurant with them on. It was like wearing a pair of zambonis.
Next I tried a pair of Ecco Dacapo Ties. Not exactly sleek, but not offensively grotesque:
These are just about ideal for big city streets: lots of support, but with decent lines. At home, I started wearing them on Fridays at work, but in summertime they were too hot.
Meanwhile, I'd looked to replace a pair of worn-out Cole Haan leather soled tasseled loafers, and found the rubber-soled Cole Haan Pinch Air Cup Penny, which were so comfortable that I bought two pairs, black and tan. Bye-bye, leather soles!
I was amazed at how much better I felt after a day on my feet at work, wearing these shoes. I tossed my scuffed, hard-worn oxfords. I was getting dangerously comfortable.
The moment of truth came standing outside the Chelsea Market in Manhattan last month. I was wearing my Eccos. I saw a man get into a taxi wearing a trim, light-weight, suede-looking pair of sneakers. They stayed with me, and I scoured Zappos trying to find them. They might have been Adidas, but I couldn't find a match. The closest thing I found were Frye's Reed Runners, so I ordered a pair.
They arrived on Monday, and I wore them to work today, a "casual Friday". I was well-pleased. They were comfortable, light, cool. They have a sort of golf/saddle shoe look with the two-tone suede. Mary in Youth Services noticed them, and said how comfortable they looked. I love my Reed Runners!
[Edit 11/14] Martin comments that he wears sandals in warm weather, reminding me that I didn't think to mention that in the summer I wear the State Shoe of Florida, the Flip-flop, like everyone else, around the house.
After a couple of days in my Frye Reed Runners, I am thinking this may in fact have been the shoe I saw in New York.