If you're going to invest your money in just one boot, you really couldn't go wrong with Viberg's new Side Zip style. The vintage miliary-inspired boot is crafted from cigar waxed deer leather from Italy and is built on a 2050 last. You've also got a leather sole, dovetail heel, kip leather lining, a natural flat welt, Goodyear welt construction, and nickel Lampo zippers for easy on and easy off. 

$730, viberg.com