Ankle Boots first appeared on Chictopia's streetstyle gallery in Winter 2009 seen on Bronx blogger DelmyMaya of FashionBananas.com. She styled her gray Boutique 9 ankle boots with a blue Gap denim shirt, black American Apparel body con dress, and gray Urban Outfitters tights. Since then, Ankle Boots have grown in popularity as bloggers from Melbourne, Los Angeles, and Denver have discovered them. Ankle Boots are generally seen in casual, chic, and bohemian style. Popular brands of Ankle Boots are Steve Madden, thrifted, Forever 21, H&M, and Zara.
There are currently 901 streetstyle photos of bloggers wearing Ankle Boots. Most recently, blogger Chaba of thrilloftheheel.blogspot.com styled her black OASAP ankle boots with a white OASAP checkered coat, red Zara bag, and black H&M sequin pants.