Pair Vintagecouture.com's metallic Roman sandals ($195, Boutique Le Trou , 940 Queen West, 416-516-7122) with opaque tights to avoid a "no open toes after Labour Day" fashion charge.
The season's stiletto is extra-pointy and super-patent ($118, Town Shoes , 131 Bloor West, 416-928-5062, and others, www.townshoes.com).
Fly's espresso suede lace-up boot ($360, Trove , 793 Bathurst, 416-516-1258, www.trove.ca) is perfect for a skinny jean stuff.
Fall footwear's buzz word is the almond toe, and this vintage embossed velvet pair ($60, 69 Vintage , 1100 Queen West, 416-516-0669) combines the bulbous point with a chic platform lift.
Step up the style on Firetrap's brown bootie ($215, Heel Boy , 682 Queen West, 416-362-4335) by snapping down its canvas cuff.