I love the chukkas, and when I saw them listed at $150 in Antenna, I thought "Must cop!". But apparently, that must be the wholesale or something. Boo.
I don't know if I'd feel comfortable banging around in $300 kicks unless I picked them up at high discount, which is the main impediment to my getting a pair.
As for them getting dirty. Not worried. They are sneakers, which, imo, always look better dirtied up.