Anne Michelle Boots

TOUGH CUSTOMER
An incredibly priced shoe-bootie has buckles and an industrial-strength platform sole.

Anne Michelle, $30; ShoeOcean.com
Kim Kardashian boots

IT'S A CINCH
This year even boots wear belts. From Kim Kardashian's addictively well-priced website.

ShoeDazzle, $39; ShoeDazzle.com
Merona boots

TRIPLE PLAY
This shapely version (with those ubiquitous buckles) is a cheap thrill.

Merona, $45; Target.com
Payless chocolate boot

HOT CHOCOLATE
Instead of black, try the more casual warmth of a brown boot.

Dexter for Payless, $45; Payless.com
Shearling payless Boot

FEELING SHEEPISH
It's faux, but no less cozy than the real deal (and a lot more affordable).

Payless, $45; Payless.com
Christian Sirriano for Payless booties

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

Christian Siriano for Payless, $50; Payless.com
Skechers boots

SO FIERCE
Big trend, little price. A slight dip in back minimizes bulk around the knee.

Skechers, $59, 800-746-3411
Tretorn Rain Boot

Be Well(ies)
Use the heel tab to slide these on smoothly when the days are slippery.

Tretorn, $60; Tretorn.com

Bakers Plaid Boot

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

Bakers, $70; BakersShoes.com
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Colin Stuart Boot

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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Volatile boot

HIGH RISE
This flat, foot-friendly boot won't tug at the knee because of the double buckle in back.

Volatile, $88, ShoeMall.com
Mia Boots

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

Mia, $89; MiaShoes.com
Sorel Boots

TAKE A HIKE
The duck boot freshens up with tweed and snake-patterned rubber.

Sorel, $95; Sorel.com

Banana Republic Rain Boot

RIDER ON THE STORM
This rubber equestrian boot is a natural puddle-jumper.

Banana Republic, $98; BananaRepublic.com
Rocket Dog boots

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

Rocket Dog, $99; RocketDog.com
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O Boot Guide
O's Complete Boot Guide:
More than 70 styles we love

From the November 2009 issue of O, The Oprah Magazine