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RACHEL Rachel Roy Ana PumpsInspired by his closet, reinterpreted for you. These sassy heels evoke a hint of menswear-inspired flair, but a pop of blush warms up the look and gives the classic pump silhouette a touch of old-fashioned, ladylike elegance. Also in tan/orange.

$119.95 at
MICHAEL Michael Kors Haven BootiesAt first glance, you might take these boots purely at face value. Sneak a closer peek, though, and you’ll find that what seems to be an average high-heeled bootie is a little more complex after all. Featuring a bright gold zipper, the boot is accented at the heel by a bold metallic panel to put a little extra pep in your step.

$195 at
DV by Dolce Vita Pavin BootsEase into colder weather in a pair of simple boots that are as classy as they come. Featuring a comfortable wedge heel that’s just high enough, these chic shoes are studded with gold hardware for a cool finishing touch.

$119 at
Tahari Bentley Riding BootsIt’s the shoe of the season! This chic riding boot is a polished option to see you through fall and into the depths of winter. I love the hint of glossy hardware that accents the heel - it’s just enough to make this boot stand out without being overwhelming. And ultimately this is such a classic shoe, perfect to pair with denim, skinny pants or a dress and tights.

$149.95 at
Report Seymore BootsThere’s no dearth of rocker-chic boots that take your look from demure to daring in a flash. But some definitely stand out over others, like this moto-inspired style by Report. Great whether you’re in jeans or opaque tights and a cute dress, they’re surprisingly versatile - and incredibly comfortable. Also in taupe.

$130 at

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