1. Lacoste Royan black and dark grey leather high-tops ($195, Town Shoes, 95 Bloor West, 416-928-5062, and others, townshoes.com).
2. Pony Feed The Cat tweed high-tops ($89.99, Balisi, 711 Queen West, 416-203-2388, and others, balisi.com).
3. Generic Surplus Military high-tops ($99, Sydney’s, 795 Queen West, 416-603-3369, sydneystoronto.com).
4. Converse Chuck Taylor Woolrich print sneaker ($85, Get Outside, 437 Queen West, 416-593-5598, converse.com).
5. Fluevog Flight JFK wine-coloured sneakers with brogue details ($205, 242 Queen West, 416-581-1420, fluevog.com).
