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You can't go wrong with the handsome Calhoun boot from Allen Edmonds. Its luxe suede upper and simple, handsome profile make this a highly versatile style, and a lightly cushioned insole and flexible textured outsole ensure you stay as comfortable as

Ben Sherman fashions the Liberation oxford in lightly distressed leather, with an apron toe and a three eyelet lace entry. The look is cool and professional, with a modern edge. A lightly padded footed adds comfort.

Matisse's Trigger offers a classic Western silhouette with contemporary, playful detailing. Whether you love it for its rich leather, contrasting stitching, or metallic floral inspired inlays, it will be a charming, versatile addition to your cool we

Cordani Women's Quinton Lace Up Ankle Boot

If you hate to be pigeonholed especially when it comes to your style step into this Biviel ankle boot. It combines the look of a rocking and rolling stomper with a quaint lace up, while shiny patent leather ups the fashion quotient.

You'll fall in love with Victorian inspired dressing thanks to this shoe from Restricted. The extra feminine silhouette has unique seaming at the toe and a slightly flared heel. The military like lacing features rows of buttons, while the side zipper

Don't let this low key lace up fool you, it's about as sassy as they come. John Fluevog's Jenna boot boasts a sumptuous leather fit and finish with topstitched details for added shape, while its wrap around ankle strap and lacing style will give you

Aptly named, this Towwer bootie from Steve Madden defies all laws of gravity. In a sky high silhouette, this bootie has a smooth leather upper with flirty ruffled detailing, pretty and polished hardware, and just about all of the sass that one person

Look sharp and stay comfortable, even in casual situations, with the Sherman boot from Florsheim. We think you'll love its hand rubbed leather or suede upper, luxe leather linings, Bio Comfort sock liner, and flexible rubber sole, and its classic sty