Leather Mini Skirt Looks. Here are 10 street style outfits that show you different ways to wear a black leather skirt. You can wear it either high-waist or low-waist. If you want a midi leather skirt, opt for it in a pencil style. Leather skirt outfits can likewise be made formal for those expert events. There are a lot of outfits that may be created with leather skirt.