#8. WINGTIP BOOTS.
Florsheim by Duckie Brown floored us with their...well, everything, but here's what's up with these wingtips. First of all, "wingtip" refers to the stitched pattern on the upper and the shoe is also sometimes referred to as a brogue. These are amazing because they're boots. The leather is pebbled, the toe is classic and not too pointy/date-rapey, and they're fucking boots. They're perfect if you feel weird about regular hard-bottoms because they're rugged and substantial but still narrow enough for tapered twill trousers. Bonus: you can still sport them with a baggier leg provided you rag-and-roll the hem.