Windsor Skirts first surfaced on Chictopia's streetstyle gallery in Fall 2011 seen on Manila/Cebu blogger Kryz of kryzuy.com. She wore her black windsor skirt with a gold WAGW top and silver windsor heels. Since then, Windsor Skirts have grown in popularity as bloggers from Manila/Cebu, Providence, and Winnipeg, Manitoba have discovered them. Windsor Skirts are generally seen in chic, casual, and business style. Popular types of Windsor Skirts are polka dot, bandage, thrifted, dress as skirt, and lace. Blogger's favorite colors are black, red, blue, and gold.
There are currently 65 streetstyle photos of bloggers wearing Windsor Skirts. Most recently, blogger Kryz of kryzuy.com styled her black windsor skirt in a streetstyle look.