Winter Skirts first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Melbourne blogger gogosushi of leblogdesushi.com. She wore her gray Sportsgirl skirt with a black portmans scarf, black Sportsgirl jacket, and black Shoobiz boots. Since then, Winter Skirts have grown in popularity as bloggers from Los Angeles, New York, and London have discovered them. Winter Skirts are generally seen in chic, casual, and classic style. Popular brands of Winter Skirts are thrifted, vintage, Zara, Forever 21, and H&M.
There are currently 17149 streetstyle photos of bloggers wearing Winter Skirts. Most recently, blogger nanysklozet of nanysklozet.com wore her maroon romwe skirt with a black Guess boots, charcoal gray desigual coat, and camel Dailylook sweater.