I'm a full on barefooter myself, really only wearing shoes while at work, or on the bike. On my KHS with platforms I typically wear my VFF's and they're been fine. At work I wear Stem Primal Origins which are pretty much the most comfortable shoes I have ever tried, and feels more like barefoot than even VFF's. However I feel like the sole material is really too soft to use with my studded platform pedals. I have some old flip flops that I use on the KHS sometimes in warmer weather, and the soles are getting torn up from the pedal studs.

I have normal-style Bontrager SPD shoes that I use on the road bike. They're not the roomiest, but they're okay. However I really like the looks of Bont shoes, which seems to be the best bet for wide toe box. Unfortunately their lowest-price shoe is still $165, though I really want to try them out one day.

http://shop.bontcycling.com/collecti...s/commuter-two