Thanks for the tips
I'm not really feeling the moc toes, though. I'm going to Chicago for grad school and was thinking more of a chukka/desert boot style. I'm basically in love with http://oakstreetbootmakers.com/footwear/natural-trench-boot (but would get vibram soles for weather)
Any suggestions for stores to buy? I'm rather new to this.
I'd suggest these - I'm sure there's a stackable code somewhere that'll bring them way down. Cheap and 2nds just means there are superficial blemishes you'd get from regular wear anyway.