High and Mighty: Tall Boots
Stuart Weitzman for Scoop reptile boots
Chunky Height
Eye-catching fake reptile skin handily energizes wardrobe basics; the chunky high heel will keep you from teetering.

Stuart Weitzman for Scoop, $675
Ecco mock croc boot
Weather the Storm
Small heels are safer than stilettos in storms, and with mock croc you needn't worry about getting your boots wet.

Ecco, $210
Coach scrunch boot
Leather Upgrade
Ladies who scrunch love the braided leather. An elastic top keeps wind and weather out (and the boot from drooping).

Coach, $598
Bally boot
Eclectic Versatility
Folkloric charm is the appeal of an embroidered suede heel that's equally great with skinny jeans or a ladylike straight skirt.

Bally, $945
Ann Taylor Loft boot
Embellished Hardware
The ease of a streamlined flat heel complements the discreet style of brass hardware (the kind usually found on handbags).

Ann Taylor Loft, $129
Naturalizer leather and suede boot
Italian Luxury (at a Reasonable Price)
A mix of leather and suede plus a rubber sole makes for a slick interpretation of a boot from a fashionable Italian designer.

Naturalizer, $179
Born crimson boots
Vibrant, Basic, Comfortable
Shapely stitching, a reasonable heel, and a vibrant crimson transform this basic boot into an everyday pleasure.

Børn, $190
Rockport boot
Perfect for Jeans
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.

Revved Up Black
A wild way to rev up black, this giraffe print is a new direction for a Palm Beach–y label.

Lilly Pulitzer, $498

See more styles in O's Ultimate Boot Guide!