What makes a city cool? There are eight ways to measure urban hipness, according to Canada Sports Betting, with metrics on the arts and cultural scene, lifestyle and recreation, dining and nightlife, and trendiness and media coverage. The gambling app's recent analysis ranks New York City highest when it comes to the cool factor, noting that it was the most Instagrammed among the 50 locations studied. Here are the 10 cities they say are coolest of the cool in North America: