H Williams Boot

CROC OF AGES
It's actually stamped leather in a subtle, carefully shaded color.

H Williams, $815; Plaza Too, NYC; 212-924-2180
Aerosoles boots

COMFORT: BLUE HEAVEN
Cloud-walk to work in flat knee-highs with fall's signature three-buckle look.

Aerosoles, $160; Aerosoles.com
Merona boots

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

Merona, $45; Target.com
Curations with Stefani Greenfield boot

WINNING STREAK
A suede boot acquires a slimming patent stripe.

Curations with Stefani Greenfield, $250; HSN.com
Daniblack boots

GET PUNKED
A surprisingly tasteful studded boot: tall, flat, black. It's punk with a better attitude.

Daniblack, $295; ShoeBox, NYC; 212-937-5750
Cole Haan boot

COMFORT: STRAP-HAPPY
Running-shoe technology makes a good-looking stacked heel a dream for the feet.

Cole Haan, $498; ColeHaan.com
Corso Como boot

FLEX AND THE CITY
A leather boot has convenient elastic side panels for on-and-off ease.

Corso Como, $285; Anthropologie; 800-309-2500 for stores
Shearling payless Boot

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

Payless, $45; Payless.com
Ecco boot

COMFORT: GOOD MILEAGE
A suede knee-high with a flat rubber sole will be your go-to weekend boot—guaranteed.

Ecco, $200; EccoUSA.com
Fratelli Rossetti boot

BEYOND THE PALE
This tender blush is not the usual boot neutral. It will put spring in your winter.

Fratelli Rossetti, $720; 212-888-5107
Payless chocolate boot

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

Dexter for Payless, $45; Payless.com
Belle by Sigerson Morrison boot

A LEG UP
The vertical seam on this supple leather wedge generates a long, slim line.

Belle by Sigerson Morrison, $495; SigersonMorrison.com
White House Black Market boot

THE SHINING
This close-fitting pull-on has a sexy vibe—more like fishnets than boots.

White House Black Market, $118; WhiteHouseBlackMarket.com
Pink Frye Boot

Berry Appealing
A juicy hue punches up a traditional style.

"Carson Pull On," The Frye Company, $348; TheFryeCompany.com
Michael Kors Boot

Zippin' Around
A staple motorcyle boot gives an edge to feminine frocks.

"Darcy boot," Michael Michael Kors, $285, Macy's; 800-622-9748
Miz Mooz Boot

All Buttoned Up
A touch of turn-of-the-century for turning heads.

"Summer," Miz Mooz, $220; InfinityShoes.com
Etienne Aigner Boots

Aren't Ya Plaid
Sophisticated and sturdy riding boots make the grade with a preppy polish.

"Vira II" in wool fabric, Etienne Aigner, $181; Shoes.com
Bruno Frisoni Boots

Trim and Proper
Soft touches and a stacked heel make a grand entrance.

Bruno Frisoni, $1,026; BrunoFrisoni.com for stores
Bakers Slouch Boots

We're Swayed
This ruched suede can also be folded up over the knee.

"Bonnie," $100; BakersShoes.com

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

From the November 2009 issue of O, The Oprah Magazine