Cut the top and bottom off of the pineapple then trim off all of the rind. Cut the pineapple in half lengthwise, remove the core, then cut each half into wedges. Arrange the wedges on paper towels and thoroughly blot off any excess moisture.
Insert a lollipop into each pineapple wedge and line a baking sheet with wax paper or parchment paper.
Melt the semisweet chocolate chips in the microwave or in a double-boiler then transfer them to a tall glass. Dip each pineapple wedge into the chocolate and shake off any excess. Place the pineapple on the baking sheet and repeat the dipping process with the remaining wedges. All the chocolate to fully harden.
Melt the white chocolate chips in the microwave or in a double-boiler then transfer them to a sealable plastic bag. Snip off the tip then pipe the chocolate across the pineapple wedges. Allow the chocolate to fully harden then serve.