Allow your cupcakes to cool completely before decorating. Line a baking sheet with wax paper and dust your working surface with a thin layer of cornstarch. Roll your fondant to be about ¼ of an inch thick and use your cookie cutter to cut out 12 fondant circles.
Next, roll spheres about one inch in diameter, you’ll need twelve of these. Flatten them out and shape them into ovals.
Roll 24 smaller spheres and shape them to look like Pooh’s ears (flat and pointed at one end).
Using a stand mixer, beat butter, icing sugar, milk and vanilla extract until smooth. Use an offset spatula to frost each of your cupcakes.
Assemble your fondant pieces: place your flat oval in the center of your large fondant circle. You can brush water on back of the oval so that it sticks onto the circle.
Using Wilton tip #7, draw Pooh’s nose and eyes with black frosting. Switch to Wilton tip #6 and draw on his eyebrows.
Place Pooh’s face on each cupcake and apply his ears (brush the back of each ear with water to secure it on his face).