The stripes with pleats look is one that I may never tire of. (See this combo on me here and here.) To breathe new life into this tried-and-true combo, try your pleated skirt with an oversized sweater in nautical stripes, or an off-the-shoulder top with ruffle stripes.
I give myself permission to buy one new pleated skirt every spring, but how do I choose?! There are so many great ones that would be at home in my closet. Here are the top contenders: