1. This shopper is part of M0851‘s new Hobo collection, which also includes shoulder bags and satchels in a rainbow of rich leathers, including a Hermès-style chestnut shade ($340, 23 St. Thomas, 416-920-4001, m0851.com).
2. Miss Rowe‘s Joplin dress is more fierce than pretty-in-pink, hand-dyed silk making it worth every penny of its $895 price tag (Missrowe.com).
3. Show off the season’s standout shoulder with Smythe‘s pouf-sleeve equestrian jacket available in black wool, camel herringbone or red tartan with a leather yoke and elbow patches ($595, Holt Renfrew, 50 Bloor West, 416-922-2333, and others, holtrenfrew.com).
4. John Fluevog has been designing killer platforms for years, so it seems appropriate that at the height of the stacked sole’s popularity he releases one of the most extreme options we’ve seen ($399, 242 Queen West, 416-581-1420, fluevog.com).
5. Maryam Keyhani‘s freshwater pearl, organza and grosgrain ribbon necklaces are the perfect frilly foil for fall’s harder silhouettes ($350, maryamkeyhani.com).