Start by carefully separating 24 regular-sized Oreos. Keep the half with the cream intact and set the other half aside. Arrange the cream-filled Oreo halves on a baking tray lined with silicone or parchment paper for easy cleanup.
In a microwave-safe bowl, melt the light brown candy melts. Follow the instructions on the bag, typically microwaving in 20-30 second intervals, stirring in between, until completely smooth.
Place a dollop of melted light brown candy onto each Oreo half with filling. Press a Popsicle stick into the candy, ensuring it’s securely placed. Add another dollop of melted candy on top of the stick, then sandwich with the other Oreo half you set aside earlier.
Separate 4 mini Oreos and discard the filling. Dip the halves into the light brown candy melts, only partially coating them. Attach two halves on the sides of each sandwiched Oreo for arms. Add two more halves on the top for the teddy bear ears.
For each pop, dip three mini Oreo halves in the melted light brown candy. Place two at the bottom of the Oreo pop to create legs, and position one more at the upper center for the snout.
Melt the dark chocolate candy melts and dip each teddy bear pop completely into the chocolate. Use a fork to help drip off any excess chocolate, then place each pop back on the baking sheet. Let them set for about 45 minutes, or until completely dry.
Melt the red and white candy melts, then transfer them into separate decorating bottles. Use the red to pipe a small Santa hat and scarf on each teddy bear, and the white to add fluffy details to the hat, along with the bear’s paws and ears.
Finally, use black decorating icing to add eyes and a cute button nose on each teddy bear pop. Let them set completely before serving or packaging them up as gifts.