Cool Boots first surfaced on Chictopia's streetstyle gallery in Spring 2009 seen on Pittsburgh blogger pamukito. She wore her brown J.Crew cool boots with a yellow Forever21 preppy sweater, blue Flying Monkey skiny jeans, and brown united colors of benetton corduroy purse. Since then, Cool Boots have grown in popularity as bloggers from Pittsburgh have discovered them. Cool Boots are generally seen in preppy style. A popular brand of Cool Boots are J.Crew.
There is currently 1 streetstyle photo of bloggers wearing Cool Boots.