The Most Comfortable Boots

Lauren by Ralph Lauren Wingtips

The men's wingtip is reborn as a classic women's weekender, complete with a no-slip sole and neat perforated details.

Lauren by Ralph Lauren, $149

Cole Haan Nike Technology Boot

Pale boots based on Nike technology feel incredible. At high risk for dirt—use protective spray immediately.

Cole Haan, $395

Low-Heeled Clarks

Smart features like covered buttons and cuffs make a sporty low-heel boot the ideal partner for jeans and a blazer.

Clarks, $130

Kors Michael Kors Duck Boot

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

Kors Michael Kors, $295

Earth Faux-Fur Nanooks

Animal lovers will adore the "fur," which is 100 percent vegan. Toggles add a Nanook feel; gum soles guarantee sure footing.

Earth, $169

The Børn Basic

Shapely stitching, a reasonable heel, and a vibrant crimson transform this basic boot into an everyday pleasure.

Børn, $190

Rockport Western Boot

Go west with casual low-heeled boots (the suede is a natural with jeans): The longer you wear them, the better they feel.

Rockport, $200.

See more styles in O's Ultimate Boot Guide!