Preppy Boots first surfaced on Chictopia's streetstyle gallery in Fall 2008 seen on Vancouver, BC, blogger lydia of styleisstyle.blogspot.com. She wore her black thrifted boots boots with a blue thrifted pinstripe dress, gray Gap sweater, and beige tights. Since then, Preppy Boots have grown in popularity as bloggers from London, Los Angeles, and New York have discovered them. Popular brands of Preppy Boots are Forever 21, vintage, Steve Madden, H&M, and Zara.
There are currently 1409 streetstyle photos of bloggers wearing Preppy Boots. Most recently, blogger Dominiquetiu of konichiwear.com styled her camel H&M boots with a ivory Zara coat, camel Hermes bag, and navy Sfera cape.