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 Los Angeles, Denver, and Indianapolis have discovered them. Ankle Boots are generally seen in casual, chic, and bohemian style. Popular brands of Ankle Boots are vagabond, Steve Madden, Forever 21, H&M, and Zara.
There are currently 942 streetstyle photos of bloggers wearing Ankle Boots. Most recently, blogger nanysklozet of nanysklozet.com wore her black H&M Trend ankle boots with a black big star denim black jeans, ivory Nordstrom Rack knit sweater, and black ted baker bag.