Pencil skirts are straight and form-fitting, typically hitting about knee length, although the hem can go both below and above the knee line. As a general rule, opt for a length that leaves a small gap between the top of your knee-high boots and the skirt’s hem; this allows for a peek of skin to keep the look fresh. If you are in a conservative office environment, a pencil skirt that hangs over your boots is certainly appropriate. Team a below-the-knee black pencil skirt with a pair of black knee-high boots and rock a crisp white button-down for the workday. Pick a fitted wrap blouse and a shorter pencil skirt for an evening out. For an equestrian vibe, opt for a camel pencil skirt, cognac riding boots and an ivory V-neck chunky-knit sweater; complete the look with simple gold accessories and a navy scarf.