Once a friend introduced me to Vibram FiveFingers, I've pretty much given up on normal footwear. Instead, I've explored several options for minimalist footwear. I'll present them here in the order I tried them.
Vibram FiveFingers KSO
Like slip-on hobbit feet.
Good for: Running and hiking, especially when it's wet, on road or off.
Not good for: Wearing all day, prolonged wet conditions, cold conditions
These are the most barefoot-like footwear I've tried. They're basically Vibram rubber gloves for your feet. Your toes can move independently, and along with the rest of your foot, they can wrap around rocks and roots on the trail for traction. They have excellent traction in almost every condition - wet wood was the only place I've felt them slip.
I've run through light snow in these, and as long as I wasn't always in the snow, my feet were fine: there's so much blood going to your toes that they stay relatively warm. I've also run through puddles after a rainstorm. Normally, I'd have to go around, but with these, I could go straight through.
However, if your feet are wet in them for a long time, it may cause problems. I wore these for a week in Peru, where it rained daily and the humidity was always high. They never really dried, which resulted in some blisters and wrinkled skin.
Also, on long runs, I've experienced some chafing along my arch. This is pretty easily solved with some athletic tape. Also, Vibram's new Bikila is said to solve the problem.
Soft Star Viley
All natural, like what the Indians wore.
Good for: Winter hikes, runs, and general wear
Not good for: Warm weather.
These are simple shoes. A smooth grain leather upper, sheepskin innersole, and rubberized outsole make them cozy, with enough traction for pretty much anything. They're super flexible - you can just roll them up - and super comfy. However, if I'm standing around inside or in warm weather, my feet sweat like crazy.
Nike Free 5.0 V4
As minimalist as Nike gets.
Good for: Situations where you need to look normal.
Not good for: Lateral movement.
These feel great after a bike ride or a long run. Their heel and arch support let my feet relax - although for most, coming from more "supportive" shoes, they would work your feet.
I don't recommend these for beginners, or really for anyone. The heel makes it extremely difficult to forefoot strike, which will give you bad form while running. Heel striking is bad. But these are very flexible as far as "shoes" go, and I avoid wearing anything with more support than these.
Nike has come out with a Nike Free Run, which doesn't seem to solve any of the problems addressed here, but does look like it has a more comfortable upper. Nike's human rights violations make me want to stay away from them.
Soft Star RunAmoc
Like what the Indians wore, but better.
Good for: Running, wearing all day, conforming a little
Not good for: Sandy trails.
Once Soft Star realized a lot of their customers were wearing their moccasins for running, they began developing a running moccasin. They sent many different variations to testers, evaluating materials, fit, and function.
They did a good job. With its perforated leather upper, Vibram sole, and adjustable elastic laces, the RunAmoc is good for running. I did 13 miles in mine the second day I wore them. However, my arches got pretty sore. It was probably not a good idea to do 13 miles on my second day. Also, sand from the trail leaked in the holes and gave me blisters on the outer part of my soles. And one more thing: the 5mm trail sole seemed to thick to me - my feet slid off rocks instead of wrapping around them.
Of course, most of those problems are my fault: I went too far too soon, perforated leather isn't good for sand, and I chose the wrong sole thickness. I sent these back for some sizing adjustments and the thinner (2mm) sole. We'll see how they work now - I'll be wearing them a lot in the DR.
In any case, these are one of two pairs of shoes I could wear all day.
Run like the Tarahumara. You don't have to get pink laces.
Good for: Running on any surface, wearing all day.
Not good for: Cold weather.
Price: $20-25, depending on foot size.
I made these myself with a kit from Invisible Shoe. That means they're custom-fitted, and cheap. The owner will make you a custom pair for twice the price.
They're a piece of Vibram rubber that hugs your sole. 4mm is thick enough to protect your feet and thin enough to let them function naturally. The cherry rubber provides good traction, along with allowing your feet to wrap around rocks and roots.
I ran on Blodgett Peak with these this morning, and they felt great. In fact, I normally couldn't feel them at all. The day after I got them, I put them on at 1400 and didn't take them off until I went to bed. They're that comfortable.