The versatile Kender ankle boot from Nine West boasts a sleek, angled silhouette for a relaxed, yet professional look. Outfitted on a modest stacked heel, this comfortable lace-up leather boot is a great choice with leggings, and the slightly burnished toebox looks great peeking out from under jeans.

• Breckelles Women's Sandy-61 Desert Ankle Boot
• Nine West Women's Illumie Pump
• Very Volatile Women's Anaconda Bootie