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 1382 streetstyle photos of bloggers wearing Preppy Boots. Most recently, blogger nanysklozet of nanysklozet.com rocked her black H&M boots with a heather gray stories by kelly osbourne sweater, black Marc by Marc Jacobs bag, and ruby red romwe skirt.