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
Smart features like covered buttons and cuffs make a sporty low-heel boot the ideal partner for jeans and a blazer.
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.
The Børn Basic
Shapely stitching, a reasonable heel, and a vibrant crimson transform this basic boot into an everyday pleasure.
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!