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Pair the skirt with a boxy jacket. This roomy, swingy piece balances the narrowness of the skirt and has a '50s ladylike appeal.
Tuck a full, dark-hued blouse into the skirt to give a dose of volume. Add black tights to winterize the look.
Pair the skirt with high-heeled boots. Just make sure that some skin (or skin covered in tights) shows, so that the line of the leg is obvious—otherwise you can look stumpy.
Belt a drapey knit jacket over a pencil skirt for a soft yet sharp effect; the nipped waist will create a pretty hourglass silhouette.