While rewatching the show in preparation for the spinoff airing on HBO Max, I noticed that there are plenty of moments where Leighton Meester and Blake Lively's characters are spotted on the Upper East Side wearing coordinated looks. The scene where they run around New York City dressed up in matching backless dresses designed by Blair's mother is one that will forever be cemented in my memory. (I know I'm not the only one who tried to replicate those photos with my best friend in high school!) From matching plaid skirts and tights to breezy, coordinated summer outfits, I'm counting down all of the times this duo prove they are the most stylish best friends on TV. Read on to see my favorite outfits.