Photos Which shoes?

The timberlands are basically new.
The brown shoes are super comfortable but very worn. I wear these to work right now.
The Tevas are new and comfortable, but when my feet sweat they tend to slide around in the shoe.
The Nikes are in good shape and very comfortable.
Not sure which one or what combination to take when I hit the road hitchhiking and whatnot.
Your thoughts?
 

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Well also something to take into consideration is your socks. Now, there's "rich people" socks (haha) with thermal blend and crazy sh!t like silk & then "working man" socks which are easily attained through Cabellas but a good wool blend is great for cooler temps & then ypur basic cotton.

Think cotton for sports shoes or sneakers & wool-blend for boots.
 
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Well also something to take into consideration is your socks. Now, there's "rich people" socks (haha) with thermal blend and crazy sh!t like silk & then "working man" socks which are easily attained through Cabellas but a good wool blend is great for cooler temps & then ypur basic cotton.

Think cotton for sports shoes or sneakers & wool-blend for boots.
also keep in mind you will go through socks like crazy, and if wearing boots daily make sure you don't sleep in them every night boot rot is a mean bitch
 
I would pick the boots and add a pair of cheap flip flips. The boots for walking/hiking and when you need good protection. The flip flops for when you want to let your feet air out and you don't need protective footwear.

I'm basically living in my flip flops. For me the most comfortable footwear. I have some boots, though. Rarely wear them.