Report Desert boot

$84
Desert boots with a twist, these have a gum wedge that gives you height—without the hurt.

Report; ReportShoes.com
Tommy Hilfiger wedge boot

$98
The menswear pattern of this wedge boot is brilliant with a trench.

Tommy Hilfiger, Macy's; 800-622-9748
Payless faux-suede boot

$38
This faux-suede and patent leather bootie has a vintage style—in a vintage port color.

Payless.com
Bongo multistrap boot

$75
A multistrap brown boot is a sturdy companion for jeans, cords, and khakis.

Bongo.com for stores
Sigerson Morrison for Target suede boot

$40
Starry silver studs on suede can dress up a work suit or hang out with black jeans.

Sigerson Morrison for Target; Target.com
Colin Stuart for Victoria's Secret boot

$98
Fringe makes this dusty rose shoe-boot a flirtatious version of the kiltie.

Colin Stuart for Victoria's Secret Catalogue; VictoriasSecret.com
Chinese Laundry boot

$89
These flexible, calf-hugging knee-highs will go beautifully with a lightweight dress.

ChineseLaundry.com
Steve Madden ruched boot

$99
These heroic purple boots have the look of a warrior princess (think Lord of the Rings).

SteveMadden.com

See more styles in O 's Ultimate Boot Guide!

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