Add the ripe banana, milk, vanilla extract, and ground cinnamon to a blender. Blend on high for 30 seconds until completely smooth and frothy.
Prepare the cold brew concentrate or brew strong coffee and let it cool to room temperature.
Fill two tall glasses with ice cubes. Pour the cooled coffee over the ice, filling each glass about halfway.
Slowly pour the blended banana milk over the coffee in each glass. Stir gently to combine.
Dust with a pinch of cinnamon and drizzle with honey if desired. Serve immediately.