MTV darling and star of The City, Whitney Port, was snapped up by the paparazzi in this frightening outfit.

Unflattering high-waisted shorts and a masculine (in a bad way) cropped button-up paired with lilac sandals? Diane von Fürstenberg hired this woman? This photo just screams, “I’m trying way too hard at being fashionable!”

(Make sure to check out our other questionable outfits.)