The Pokemon Wearing Glasses meme celebrates the aesthetic of stylish pocket monsters, most famously rooted in the Squirtle Squad from the 1990s anime. These sunglasses-wearing Squirtles became an early internet symbol for 'coolness' and the 'Deal With It' attitude. Today, the template has expanded to include various Pokemon wearing reading glasses or shades to portray different personas, ranging from the intellectual over-analyzer to the unshakeable boss. It is frequently used to mock newfound confidence or to provide a humorous take on being over-prepared for a minor challenge.