1) Unisex Chuck Taylor All-Star rubber sneaker ($65, converse.com)
2) Palladium Morace boot ($130, Little Burgundy, 220 Yonge, 416-260-0497, and others, littleburgundyshoes.com)
3) Blundstone 1431 Burgundy Rub ($199.95, Australian Boot Company, 698 Queen West, 416-504-2411, and other, australianboot.com)
4) John Varvatos Collection cap-toe leather boots ($898, Harry Rosen, 82 Bloor West, 416-972-0556, and others, harryrosen.com)
5) Cybranet boot ($140, Aldo, 332 Yonge, 416-596-1390, and others, aldoshoes.com)