Aigle Miss Juliette Liberty short boot ($195, Gravity Pope, 1010 Queen West, 647-748-5155, gravitypope.com)
Hunter Bakerson sneakers ($150, The Bay, 176 Yonge, 416-861-9111, and others, ca.hunter-boot.com)
Melissa by Vivienne Westwood Lady Dragon heeled sandal ($164.54, Asos, asos.com)
Joules Larkdale canvas print welly ($48.60, joules.com)
Hunter Original Nightfall rain boots ($235, The Bay, ca.hunter-boot.com)