Preppy Dresses first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Fort Lewis blogger ClothesHorse of theclothes.blogspot.com. She wore her blue Sample pinstripe dress with a blue Ralph Lauren blazer jacket, red floral, vintage scarf, and black H&M ballet, flats shoes. Since then, Preppy Dresses have grown in popularity as bloggers from San Francisco, Los Angeles, and London have discovered them. Popular brands of Preppy Dresses are vintage, thrifted, Zara, Forever 21, and H&M.
There are currently 2253 streetstyle photos of bloggers wearing Preppy Dresses. Most recently, blogger pancakeSTACKER of pancakeSTACKER.com wore her navy Twice paisley dress with a red thrifted sweater, white Jigsaw London tote bag, and tan Nine West sandals.