Preppy dresses first surfaced on Chictopia's streetstyle gallery in Summer 2008 seen on Lancaster 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 thrifted, vintage, Zara, Forever 21, and H&M.
There are currently 2276 streetstyle photos of bloggers wearing Preppy dresses. Most recently, blogger MarlaSinger of theversicle.com styled her brick red new look tartan dress with a ruby red asos suede western ankle boots, navy Ebay wool beret hat, and navy PERSUNMALL preppy structured bag.