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, New York, and Los Angeles have discovered them. Popular brands of Preppy Boots are Forever 21, Steve Madden, vintage, H&M, and Zara.
There are currently 1294 streetstyle photos of bloggers wearing Preppy Boots. Most recently, blogger artinourblood of artinourblood.blogspot.com styled her H&M slouchy over the knee boots with a Ralph Lauren officer jacket and OASAP sailor skirt.