S/Double Postman Boot

One of the most simple and refined work chukkas on the market. While they're tough enough to wear with work trousers and denim, the black leather and sleek silhouette means you could easily get away with wearing them for black tie affairs et al. Obviously ripped off the recently revived Red Wings, this version has a more streamlined design; a slightly slimmer toe box and no tacky brand tags stitched on. The only thing I'd change are the metal eyelets which would look better coated in black (and maybe swap the black calfskin for black cordovan).

$260 at the S/Double Shop