Riding Boots first surfaced on Chictopia's streetstyle gallery in Fall 2008 seen on Berkeley blogger connie. She wore her black vintage riding boots with a black Ryn: shearling jacket, gray Tsumori Chisato silk blend top, and red H&M pashmina scarf. Since then, Riding Boots have grown in popularity as bloggers from Toronto, Albany, and San Francisco have discovered them. Riding Boots are generally seen in casual, comfortable, and chic style. Popular brands of Riding Boots are Charlotte Russe, Aldo, Call it Spring, Zara, and vintage.
There are currently 130 streetstyle photos of bloggers wearing Riding Boots. Most recently, blogger luluetty of lululetty.com styled her brown J.Crew riding boots with a red vintage pheasant blouse, beige vintage breeches pants, and beige vintage tweed blazer.