Loeffler Randall medium boots

Standout
The rich look of faux snakeskin can make a brown boot stand out in a crowd. Nice with chocolate tights.

Loeffler Randall, $725
Carlos by Carlos Santana medium boots

Trim and Proper
Metal zipper trim elegantly adds a touch of industrial chic (and some ultraslimming lines) to a very ladylike suede stiletto.

Carlos by Carlos Santana, $169
Ugg Australia boots

The New Uggs
This plum gorgeous knit bootie is as snug as a bedroom slipper but a lot sturdier. Fold it down (as shown), or wear higher.

Ugg Australia, $140
Charles David boots

Hip Definition
A hip downtown attitude comes built into this black heel—the strap defines the ankle the way a belt does your waist.

Charles David, $450
Kors Michael Kors boots

Go Wild
Hunting, fishing...commuting? With this witty citified version of the duck boot, you can handle fowl—er, foul—weather.

Kors Michael Kors, $295
Covington boots

Classic Style
Fadproof, this timeless boot will upgrade the simplest outfit. For endless-looking legs, tuck your leanest black pants into them.

Covington, $125
Earth boots

Furry Comfort (And Vegan Friendly!)
Animal lovers will adore the "fur," which is 100 percent vegan. Toggles add a Nanook feel; gum soles guarantee sure footing.

Earth, $169
London Fog purple boots

Practical Comfort
Deep purple and a glossy zipper placket make practical suede—lined, water resistant—into something glamorous.

London Fog, $120

See more styles in O's Ultimate Boot Guide!
From the November 2008 issue of O, The Oprah Magazine