17 Great Ankle Boots
Your boot search is over! Here are our picks for the best ankle boots this season.
By Katherine B. Weissman

GREAT BUY: SO FIERCE
From a Project Runway winner, faux-snake boots with a spiky heel.
Christian Siriano for Payless, $50; Payless.com
Christian Siriano for Payless, $50; Payless.com

COMFORT: ALL TIED UP

COMFORT: CUTE AS A BUTTON
If you have a vintage soul, these old-fashioned boots are the next best thing to a thrift-shop find.
Söfft, $151; Sofftshoe.com
Söfft, $151; Sofftshoe.com

ZIP DRIVE
Metal trim gives an industrial feel; distressed leather makes for a broken-in look.
Twelfth St. by Cynthia Vincent, $350; Shopbop.com
Twelfth St. by Cynthia Vincent, $350; Shopbop.com

GOOD AT DETAILS
This boot synthesizes cuffs, zippers, and a platform sole into one handsome package.
Diane von Furstenberg, $395; 646-486-4800
Diane von Furstenberg, $395; 646-486-4800

THIS STUD'S FOR YOU

COMFORT: ROOM AT THE TOP
Elastic in back makes this perfect with tucked-in pants.
Modern Vintage, $295; ShopModernVintage.com
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Modern Vintage, $295; ShopModernVintage.com
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GREAT BUY: CRUSH OBJECT

GREAT BUY: SNOW DAY
From a label known for indoor attire comes this faux-shearling platform.
Colin Stuart for Victoria's Secret Catalogue, $79; VictoriasSecret.com
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Colin Stuart for Victoria's Secret Catalogue, $79; VictoriasSecret.com
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PURPLE HAZE
This leather boot with snakeskin trim reflects the season's '80s obsession.
Devani, $165; ShoeBox, NYC; 212-937-5750
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Devani, $165; ShoeBox, NYC; 212-937-5750
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GREAT BUY: FOREVER PLAID

TAKE NO PRISONERS
Let clashing tights or skinny jeans peek through this deep-brown stunner; the zip front and cage sides on these reptilian ankle booties are simply striking.
Donna Karan; $6,200; 866-240-4700 for stores
Donna Karan; $6,200; 866-240-4700 for stores

SHOW SOME SKIN
The python heel will add a slither of sleek to your winter looks.
Dries van Noten; $635; MonaMoore.com
Dries van Noten; $635; MonaMoore.com

RING THE ALARM
Fire engine-red ankle boots heat up any ensemble.
"Fifres," Christian Louboutin, $1,195; 212-255-1910

O's Complete Boot Guide:
More than 70 styles we love
"Fifres," Christian Louboutin, $1,195; 212-255-1910

O's Complete Boot Guide:
More than 70 styles we love
From the November 2009 issue of O, The Oprah Magazine