Cut cold butter into cubes and place in a large bowl. Add brown sugar, and vanilla and blend until creamy using a pastry blender or electric mixer. Preheat oven to 325.
Add flour + salt. Continue to blend until the mixture begins to form a dough that you can press together with your hands. Add toasted coconut and cut in until fully combined.
Spray a parchment-lined surface with non-stick spray and a rolling pin. Roll out to 1/8 inch thick. Place in fridge for 5 min. Test dough firmness cutting out one pineapple.
Cut out as many pineapples as you can and place them on an ungreased cookie sheet. Bake for 20-25 minutes or until the edges are golden brown. Place on a wire rack to cool.
Trace the edges of the pineapple tops and fill them in right away. Use the end of the nozzle or a toothpick to swirl and smooth out the icing.
Continue with this process until all pineapple tops are iced. Mix the yellow icing and repeat the proces on the pineapple bottoms. Decorate with sprinkles.