The Tsubo Winslow II [$240] is a brogue that is built for comfort but looks like it was designed by an artist interested only in making it look great. These shoes trace their roots to Scotland and Ireland where brogues where constructed with perforations, allowing water to drain when crossing wet terrain such as a bog. While brogues were traditionally considered to be country footwear not appropriate for casual or business occasions, brogues are now considered appropriate in most contexts. These bad boys feel like a dream and are as impressive to the eye a they are to your feet. Tsubo’s small team of designers are passionate about creating innovative design-driven footwear and that is clearly evident in the Winslow II.

Buy: Tsubo