I figure people here may have some useful suggestions for casual (non-trail) shoes. I don't want to wear my Inov-8s constantly, but they're the only shoes that I can wear all day without getting uncomfortable.

The main problem is that I have wide toes. People in shoe stores insist that I'm size 7.5 and that I don't have wide feet. However, my right little toe completely overhangs the insoles in size 8 shoes. Trail runners feel OK since the upper is so soft and malleable. Most leather shoes aren't as flexible, so my toe gets squeezed too much.

If I go up from size 8, the shoes are too long (even size 8 is frequently too long). If I get wide shoes, the rest of the shoe doesn't fit properly. I've tried stuff from Camper, Keen, L.L.Bean, New Balance, and Patagonia, all to the same effect.

Besides getting custom shoes, does anyone have suggestions for shoes
that have really wide toe boxes, or are soft and flexible enough to
not squeeze my toes?

I need a wide toebox and wear the Patagonia toast and jam. Rockports have worked well for me in the past as well. The rest of the time I wear crocs or flipflops.

I think I have the same problem. In my case nearly all shoes squeeze my little toe under the next one and I get a blister. My solution is to cut a hole in the insole for my little toe to allow it to drop down and give it room downwards as shoes do not give it room sideways. I then dropped half a shoe size and inov8 roclites fit really well

Doc Martens. Nothing even comes close.

My first question is why not wear your inov-8 constantly? That was my solution for several years. :-) Like you, I have a narrow foot but need a large toe box and had trouble finding shoes that worked for me. This year I started wearing vivo barefoot shoes which are basically hi-tech moccasins. I have found them even more comfortable for me than my beloved inov-8 310 flyrocs. I have a friend who swears by the vibram fivefingers but I have no personal experience with them.

--Mark

PS: Since the vivo barefoot shoes were so comfortable for me around town, and had great traction on the streets I tried them on a couple of back country trips. Traction was so poor that they felt a bit dangerous... Inov-8 are still my outdoor shoe of choice.

Thongs, or flip-flops.

Keens; I've never seen a wider toebox...

Luckily my office has no dress code, so Inov-8s are OK, but I do sometimes want something dressier than sneakers.

Before I found Inov-8, I was wearing Keens. I liked them at the time, but I can't go back now, I find them too constrictive. Years earlier, I used to wear Docs, but the last time I tried them, I found them uncomfortable (can't remember why now, but I think it had to do with the heel being too elevated).

Vibram Fivefingers are really comfortable, but not ideal for city walking (which is sadly what I do most often, not many chances to get into the woods recently).

I have been curious about the Vivo Barefoot shoes. I've been reluctant to try them simply because I haven't found a place locally to try or a place that offers free return shipping. Maybe if I get to NYC.

Try SAS Shoes

I wore Rockports for many years until they moved production to Vietnam (not to knock Vietnam), and their lasts (the mold for shoes, so to speak) changed, and they no longer fit properly. It seems Rockport, which used to use an American last, switched to a European last, the difference being the last angle, or the angle between the front and rear of the shoe (just look at the sole of any shoe). Bicycling magazine used to (maybe they still do) publish the last angles for shoes: angles of 10-12 deg. were best suited for American feet, angles of 15 deg. were for European feet. (This was important as many cycling shoes were imported from Europe.) I'm convinced the older Rockports used a 10-12 deg. last angle, the newer ones use a 15 deg. last. Even Keen seems to use the 15 deg. last.

Anyway, the SAS shoes are a joy, better than the old Rockports. The only catch is they're only sold thru brick-and-mortar SAS stores, and the one I know is in Lancaster, PA. They insist on measuring your foot with the Brannock device, but they sure know what they're doing: they moved me from a 11 Wide to a regular 10.5, which was a good move. I do wish they made a trail shoe!

SAS is opening a store just south of Pittsburgh this weekend. I can try to check it out after the outlet center grand opening events end.