Mix together the flour, salt and baking powder in a bowl. In a separate bowl, cream the butter and sugar with an electric mixer until it becomes light and fluffy. Add the milk to the mixture along with the egg and vanilla, and mix well. Then slowly add the flour mixture until it is just combined.
Shape the dough into a ball, then divide it into two balls. Wrap them in plastic wrap and place in the refrigerator for 1 hour.
Lightly dust some flour onto your countertop, and roll the dough out until it is ¼ inch thick. Cut out right and left shoe shapes from parchment paper to use as stencils. Cut out shoe shapes from the dough using the stencils. Cut out rectangles from the remaining dough, so that you have 1 rectangle for each shoe.
Stick a lollipop stick onto the underside of each cookie rectangle. Place the rectangles and the shoe cookies on a baking sheet lined with parchment paper. Bake the rectangle cookies for about 8 minutes at 350F and the shoe cookies for 10-13 minutes at 350F, until lightly golden. Transfer these to cooling racks and allow to fully cool.