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 Hong Kong, Manila, and Los Angeles have discovered them. Popular brands of Preppy Skirts are thrifted, vintage, Zara, H&M, and Forever 21.
There are currently 3148 streetstyle photos of bloggers wearing Preppy Skirts. Most recently, blogger joujouvilleroy rocked her sky blue redvalentino white flower skirt with a navy Louis Vuitton embroidery velvet blazer, black Louis Vuitton vivienne bag bag, and white Sergio Rossi open heels.