With your oven preheated to 375 F, mix butter 1/2 cup powdered sugar, salt and vanilla extract in a stand mixer for about 2 minutes until evenly incorporated.
While your stand mixer is stirring on medium low setting, gradually add in flour until it turns into a dough.
Place onto a large cookie sheet (or two medium sized cookie sheets) lined with parchment paper. Bake 8-10 minutes until the bottom is light brown. Transfer to a cooling rack and let cool for about until its cook the touch.
Add 1/4 cup powdered sugar to a bowl or plate and roll cookies into powder sugar until evenly coated and place back on cooling rack.
Once cookies are completely cooked (about 10 minutes) place crushed candy canes on top of the cookies and enjoy!