The midi skirt can appear to be a baffling sartorial choice. The seemingly awkward mid-calf length risks frumpiness, while the volume can make a girl feel bigger than her actual numbers suggest. So why on Earth should you wear one? Because it’s trendy! No. No. That’s not the right answer. Take two. Because it’s chic! Think Grace Kelly in To Catch a Thief or Audrey Hepburn in Roman Holiday. It’s a sophisticated, elegant option that can actually elongate your frame and create a decidedly feminine silhouette. If you’ve got a finely tuned internal chic-o-meter that can gauge with near perfect accuracy the success of an outfit, then you should try the look with flats. Otherwise, a little extra height from a high heel or wedge shoe will go a long way to assuaging any frumpy-fears you might still be harboring. Keep proportion in mind and pair with a nicely tailored top, tucked in, and you’re well on your way to acquiring Olivia Palermo-level style cred.