Jean Shop’s leather knapsack ($1,188, Lileo, 55 Mill, building 35, 416-413-1410, lileo.ca) has a luxe but lived-in look. Buffalo check shirt jacket ($98, Gap, 60 Bloor West, 416-921-2225, and others, gapcanada.ca), slacks as before. Converse Woolrich plaid boots ($140, Get Out Side, 437 Queen West, 416-593-5598, converse.com).
