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For an unexpected pairing, balance out a pleated skirt with an oversized leather jacket (make sure the jacket is slightly cropped to accentuate the flowy nature of the skirt). Then, pile on the pieces: This combination is just asking for a thick pair of stockings, a heavy scarf or two (try a patterned style to add some texture), some statement-making boots (these offer the versatility of a black pair but aren’t as boring), and a coordinating bag. Basically, your accessories do all the work—and give your most prized pieces the ability to pull double-duty.