Nine West Women's Despina Boot

A wide, suede cuff with brass button detail, gives this Nine West knee-high, its distinctly chic character. Match this pointy-toed, sixteen-inch boot with an tailored overcoat and navigate through winter in style. We think that the back-zip, rising from the three-inch stiletto heel, makes this boot especially sexy.

Jessica Simpson Women's Yana Boot

The "Yana" boot from Jessica Simpson steps up the sexy with scrunched details, metallic decor and a stacked heel.

Charles by CHARLES DAVID Women's Swish

Sashay your way through the day in the stunningly beautiful Swish dress boots from Charles by Charles David. Faux crocskin leather upper in a dress boot style with a round toe. Full-length zipper closure at side, elastic goring at top of shaft for easy fit. Smooth lining, lightly cushioned insole, dress style midsole, smooth traction outsole. 16 inch shaft, 13 1/2 inch circumference. 4 inch covered heel.

Charles by Charles David Women's Sceptre Bootie

This sleek bootie from Charles by Charles David, with its Sceptre-like heel, is bound to make a statement. Its stretchy fabric upper features strappy overlays and a thin belt that lend to the architectural appeal of the design. Regardless of what you pair it with, this shoe promises to stand out in a big way.

FRYE Women's Adrienne Button Tall Boot

The most admired American fashion designers show a touch of buttoned-up propriety in their collections, and Frye's Adrienne boot will fit that aesthetic perfectly. This gorgeous boot also has a military/Victoriana influence that'll prove to be groundbreakingly chic.

Nine West Women's Ealene Boot

The Nine West Ealene is one smart-looking boot, with a full-length side zip and a resilient leather upper that will keep your feet snug and warm on crisp fall mornings. The wide entry and pull tab, along with a slight bevel to the shaft, make for easy dressing, while the stacked heel and square toe design add a nice feminine touch.

Rockport Women's Chutney Lace Up Side Buckle Boot

A tucked and tailored casual ensemble needs a sophisticated boot like the Rockport Chutney. Smooth leather upper with round toe, neatly seamed toe overlay and scalloped heel overlay, 15 inch zippered shaft, 15 inch circumference collar with folded leather side gore and dual leather tapered straps with metal buckle embellishment at top of shaft, 6 inch hi-rise front shaft grommeted lacing overlay. Fabric lining, cushioned leather insole, textured rubber outsole, 1 1/2 inch square heel.

FRYE Women's Heath Outside Zip Boot

Frye's Heath shows off its zipper as both fashionable and functional.