Vintage 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, Vintage Riding Boots have grown in popularity as bloggers from Orange County, Smalltown, and Toronto have discovered them. Vintage Riding Boots are generally seen in classic, grandma, and 50s style. Popular types of Vintage Boots are lace-up, ankle, combat, lace up, and cowboy.
There are currently 8 streetstyle photos of bloggers wearing Vintage Riding Boots. Most recently, blogger luluetty of lululetty.com wore her brown vintage riding boots with a black Target hat, black J.Crew cardigan, and red Forever 21 stripe top.