1. Beat Kerouac cognac toe cap ($205, Fluevog, 242 Queen West, 416-581-1420, fluevog.com).
2. Prada brown brogues ($625, Holt Renfrew, 50 Bloor West, 416-922-2333, holtrenfrew.com).
3. Philip Sparks brown woven dress shoes ($145, Town Shoes, Eaton Centre, 220 Yonge, 416-979-9914, and others, townshoes.com).
4. Vintage Florsheim burgundy brogues ($120, Klaxon Howl, 694R Queen West, 647-436-6628, klaxonhowl.com).
5. Vintage Royal York brown lace-ups ($120, Klaxon Howl).
