I used to swear by AirWalks but I think they lost quality in the last few years.
Anything that is a natural material, especially leather, will usually hold up better.
although I prefer shoes I think boots are the way to go in general. It takes longer to break them in, I wouldn't walk miles and miles in a brand new pair of boots. I say that because I've done it and it sucks. But as far as ankle support, durability and traction go a good pair of boots can't be beat. Especially a military style boot. There is a reason the militaries of the world wear boots.
What ever method you use to acquire footwear, get something good. I've learned over the years that good footwear can be one of your most important pieces of gear. If your feet get fucked up from some shitty shoes, you aren't going to get very far.
And like someone else said, use baby powder or foot powder. Even if you don't think you need it.