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In a mixing bowl, beat the softened cream cheese until smooth and creamy.
Add the powdered sugar and vanilla extract, mixing until fully blended and no lumps remain.
Fold in the whipped cream gently until the mixture is light and fluffy.
In a separate bowl, whisk the instant banana pudding mix with the cold milk for 2 minutes until slightly thickened.
Combine the banana pudding mixture with the cheesecake mixture, folding gently until both are fully incorporated.
Fill each waffle cone about halfway with spoonfuls of the cheesecake-banana pudding mixture.
Add a couple of banana slices and a sprinkle of crushed vanilla wafers on top of the first layer.
Fill the cones to the top with more cheesecake-pudding mixture.
Top each cone with a swirl of whipped cream, more crushed wafers, a drizzle of caramel (if using), and extra banana slices and vanilla wafer pieces as garnish.
Serve immediately or chill the cones for up to 2 hours before serving for a firmer texture.