Artist Tracy Lolita Healy designs the most distinct wine glasses, like this one: Which Shoes? 15oz Wine Glass (6004429) by Lolita. Why do witches wear pointed toe shoes? It helps make flying on their brooms easier due to the proper aerodynamic shape. Besides shoes, this wine glass features spiders and spider webs? the perfect Halloween gift for your wine-drinking friend who also loves shoes and spiders. Wine glass collectors also appreciate this unusual glass.