Preppy Skirts first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Los Angeles blogger taghrid of taghrid.cc. She wore her white f21 skirt with a beige Target isaac mizrahi sweater, brown vintage belt, and brown Nine West shoes. Since then, Preppy Skirts have grown in popularity as bloggers from Los Angeles, London, and Hong Kong have discovered them. Popular brands of Preppy Skirts are thrifted, vintage, Zara, H&M, and Forever 21.
There are currently 3551 streetstyle photos of bloggers wearing Preppy Skirts. Most recently, blogger Dominiquetiu of konichiwear.com styled her navy F&F skirt with a camel Chanel bag, ivory Stradivarius top, and camel Stradivarius cardigan.