Photo: Ben Goldstein/Studio D; styling: Claire Tedaldi for Halley Resources
1. 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
2. Weather the Storm
Small heels are safer than stilettos in storms, and with mock croc you needn't worry about getting your boots wet.
3. Leather Upgrade
Ladies who scrunch love the braided leather. An elastic top keeps wind and weather out (and the boot from drooping).
4. Eclectic Versatility
Folkloric charm is the appeal of an embroidered suede heel that's equally great with skinny jeans or a ladylike straight skirt.
5. 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
6. 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.
7. Vibrant, Basic, Comfortable
Shapely stitching, a reasonable heel, and a vibrant crimson transform this basic boot into an everyday pleasure.
8. 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.
9. 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, $498See more styles in O's Ultimate Boot Guide!