I just picked up a pair of navy blue Sanuk Standards on sale for $40. Pulled out the insole & it makes an awesome barefootesque everyday casual work shoe that can go with jeans/khakis and sockless with shorts come summer. I have 2 pairs of $10 shoes I picked up at Wally World, one pair black one pair tan that are flathealed and bendy. They look like Chinese shoes and I use them quite a bit with slacks. The wife hates them though I bought some Feiyue off Amazon but don't care for them much. Not a fan of the rounded sole. Also, They run a little smaller to size and mine crush my toes. They look cool though and I would probably wear them quite a bit if they were the proper size. Another good score I had was $12 for a pair of Margaritiville canvas sneakers I found on clearance at Marshalls. These things are sweet. They look exactly like Converse Thin Chucks without the $40>price tag!
I'm waiting for a sale on the NB Minimus Trail. Tried them on the other day at the store. I love those bad boys but refuse to drop $100 on them. They get down to $75 and I'll pull the trigger though. Like others have said, they will last a long time. They are super versatile as an all-around sneaker from what I can tell. I have VFF's and like them for running, walking, hiking etc...but it does get kind of annoying always being asked about them and stared at in public. Not a huge fan of wrestling on my shoes whenever I wan't to wear them either. I have Rip Curl Surf Booties for winter surfing & was using those for trail running before I got my VFF's. They were awesome for ground feel but they got FREAKIN' HOT after 30 minutes in the Florida sun.
I have one "normal pair" of Black Docker loafers left over after transitioning to minimal shoes for the last year & 1/2. I save those to wear to funerals & weddings
Eh, people always say to take it easy when starting out. I have flat feet (HAD actually, VFFs have helped my arches grow back) and didn't start off TO slow. After spending eight months in boots I came back home, got a new pair of VFF's and hiked 4.5 miles in them and was more or less fine. Some muscle soreness but nothing to grip about. I also usually run on either a rubberized or clay track which helps with impact as well. Was never a fan of pavement running even when I wore running shoes. I like the VFFs because of the individula toe slots, really helps when hiking and powe lifting I think, you can actually feel your toes moving individual to get traction on the ground, cool expierence.
Another alternative are gymnast\ballet flats. The real ones made for athletes. Quite cheap, quality construction and extremely minimalist. The split sole type are really comfortable and allow your foot maximum movement and flexibility. Once you scuff up the leather soles they are very grippy. They only come in white\black or pink but can easily be dyed any colour you like. They also fold up to nothing when you take them off. I always keep a few pair kicking around at home.