Ash ankle boots

CUFF LOVE
This ankle-high wedge has material to spare.

Ash, $200; Shopbop.com
Christian Sirriano for Payless booties

GREAT BUY: SO FIERCE
From a Project Runway winner, faux-snake boots with a spiky heel.

Christian Siriano for Payless, $50; Payless.com
Clarks Lace Up Boot

COMFORT: ALL TIED UP
This lace-up style with a low stacked heel hugs the ankle.

Clarks, $140; ClarksUSA.com
Sofft button boot

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
Twelfth Street by Cynthia Vincent Boots

ZIP DRIVE
Metal trim gives an industrial feel; distressed leather makes for a broken-in look.

Twelfth St. by Cynthia Vincent, $350; Shopbop.com
Mia Boots

GREAT BUY: DELICATE MATTER
This dainty boot laces up in back like a corset.

Mia, $89; MiaShoes.com
Diane von Furstenberg boot

GOOD AT DETAILS
This boot synthesizes cuffs, zippers, and a platform sole into one handsome package.

Diane von Furstenberg, $395; 646-486-4800
Miu Miu boots

THIS STUD'S FOR YOU
A graceful pattern takes the menace out of heavy metal.

Miu Miu, $870; Net-a-Porter.com
Modern Vintage Boots

COMFORT: ROOM AT THE TOP
Elastic in back makes this perfect with tucked-in pants.

Modern Vintage, $295; ShopModernVintage.com
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Nine West Military Boots

ON THE MARCH
A military-style army green boot gets a flirty heel.

Nine West, $149; NineWest.com
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Rocket Dog boots

GREAT BUY: CRUSH OBJECT
Precreasing makes it easy to achieve the scrunched-down look.

Rocket Dog, $99; RocketDog.com
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Colin Stuart Boot

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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Devani boots

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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Bakers Plaid Boot

GREAT BUY: FOREVER PLAID
This buttoned-up boot lets you test-drive fall's dominant pattern.

Bakers, $70; BakersShoes.com
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Donna Karan boot

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
Dries van Noten boot

SHOW SOME SKIN
The python heel will add a slither of sleek to your winter looks.

Dries van Noten; $635; MonaMoore.com
Christian Louboutin boot

RING THE ALARM
Fire engine-red ankle boots heat up any ensemble.

"Fifres," Christian Louboutin, $1,195; 212-255-1910

O Boot Guide
O's Complete Boot Guide:
More than 70 styles we love

From the November 2009 issue of O, The Oprah Magazine