Buy It Now at Martin Patrick 3, $475

The Pepin Boot is a masterpiece from this relatively new label, and it's a boot for all aspiring stylish dudes. The sexy-ass Jodhpur-style boot with burgundy Chromexcel uppers and crepe sole is out of the ordinary, which is perfect for style's "clothes get weirder" attitude of today. And the fact there's only one current location that carries them in the U.S. along with world famous United Arrows in Japan means that these are hecka exclusive.