Coolway Boots first appeared on Chictopia's streetstyle gallery in Fall 2009 seen on Florence blogger Annachiara of anyannachiara.blogspot.com. She styled her gray Coolway boots with a black Zara t-shirt, gray Zara blazer, and blue Zara shorts. Since then, Coolway Boots have grown in popularity as bloggers from Athens, Florence, and Barcelona have discovered them. Coolway Boots are generally seen in casual, chic, and urban style. Popular types of Coolway Boots are tacks, studded, and black boots. Blogger's favorite colors are dark brown, black, gray, and brown.
There are currently 64 streetstyle photos of bloggers wearing Coolway Boots. Most recently, blogger Victimofmycloset of victimofmycloset.blogspot.com.es wore her Coolway boots with a Stradivarius coat, suiteblanco jeans, and Bershka jumper.