Barneys New York Bi-Color Chukka
Buy It Now at Barneys, $185

With their simple suede and crepe sole construction, desert boots have stood the test of time and trends. Sure, you can definitely cop a classic version from Clarks or one of their many Supreme collaborations, but this two-toned take from Barneys is worth a look too. The difference in the suede colors is subtle enough to make someone take pause, but not so ridiculous that it looks foolish.