For Spice Mix: Combine ingredients. Store in airtight container at room temperature until ready to use.
For Caramelized Sugar: Heat sugar in saucepan on medium-low heat until it melts and turns a medium caramel color. Pour onto half sheet pan lined with a silicone mat. Spread evenly in a thin layer. Cool completely. Break into pieces. Process in food processor to a fine texture.
For Shake: Cut banana lengthwise into 4 pieces. Place 3 pieces in blender container. Add ice cream, milk, 2 oz. cookie pieces, 1 oz. Caramelized Sugar and 1/4 tsp. Spice Mix. Blend until smooth. Pour into 16-oz. serving glass.
Sprinkle remaining banana piece with 1/2 tsp. Caramelized Sugar. Arrange near edge of glass. Garnish drink with piped whipped cream, remaining 1/2 oz. cookie pieces and 1/4 tsp. Caramelized Sugar.