Lucchese Evan chocolate gator, $1495 https://www.lucchese.com/shop/boots/evan/GY8002 http://www.allensboots.com/mens-lucchese-bootmaker-evan-chukka-gy8002-gy8002.html I'm too cheap of a person though...to spend $1500 on shoes. Even if I have a killer day in the market, don't matter. My personal spending habits remain the same.
Shoes is one of things I am willing to spend more money on (not that much though), for purely practical reasons. Higher quality shoes are often more expensive, and having higher quality shoes means your feet are warm, comfortable and dry even in the worst weather.