You’re more Serena than Blair. A pair of elegant, equestrian-tinged boots are walk-around-town comfortable and pop-into-Chanel-on-a-whim chic.
From top: "Waggin," $179, Nine West, select Macy's, 800-298-6229; Leather "Deirdre," $945, Ron White Signature Collection, ronwhiteshoes.com; Suede "Toowoombah," $219, emuaustralia.com
You can’t get enough of the Eighties. And though you like being comfortable, you can’t buy another pair of ballet flats.
Clockwise from top left: Calf-hair "Thayer," $98, BCBG Max Azria, bcbg.com; Patent and napa leather "Rockstud," $595; Valentino Garavani, 212-772-6969; Fishskin, $129, All Black, endless.com
Pointy Ankle Boots
You’re on the trend’s leading edge. And totally over the round toe.
From top: Studded leather "Fidelia," $159 (avail. late Oct.), Guess, guess.com for stores; Suede and calfskin "Anne," $850; Edmundo Castillo, edmundocastillo.com for stores; Chain detail, $375, Marc by Marc Jacobs, select Barneys New York, 888-8-BARNEYS
Stacked Heel Boots
You’re no-nonsense, but feminine. You like to walk to work, but your wardrobe’s full of pretty, flattering dresses.