FOR THE GINGERBREAD: 

1. Cream butter, eggs, vanilla. Use a stand mixer or large bowl with electric beaters to beat the butter for 60 seconds. Add the brown sugar and molasses and beat on medium high speed until creamy. Stop the mixer and scrape the sides.  Add egg and vanilla on high speed for 2 more minutes. Stop again and scrape the sides. It’s okay if the butter looks separated.
2. Mix dry ingredients. Use a second bowl (or a sifter) to whisk the flour, baking soda, salt, ginger, cinnamon, allspice, and cloves together. Slowly add the flour mixture to the butter, a little at a time, mixing on low in between. Your dough should be thick and sticky.
3. Chill dough. Divide dough in half and place each onto a large piece of plastic wrap or bowls with lids.  Chill for at least 3 hours and up to 3 days. Do not skip this step. If baking with kids, consider doing all of this the night before.
4. Prep pans and oven. Preheat oven to 350°F . Line 2-3 large baking sheets with parchment paper or reusable silicone baking mats.
5. Roll dough and cut cookies. Use half of the chilled dough at a time (leave the second half in the fridge). Sprinkle lots of flour on a clean surface and use your hands and a rolling pin to flatten the disc in a large, round shape. It’ll be sticky so keep adding flour as needed. Your dough should be 1/4 inch thick. Cut into 3-4 large star shapes. Place shapes 1 inch apart on prepared baking sheets. Re-roll dough scraps until all the dough is shaped. Repeat with remaining disc of dough, cutting into 6-8 smaller and smaller star shapes. 
6. Bake. Bake large cookies for about 12-14 minutes, but keep an eye on them! For the smaller cookies, set a timer for 8 minutes. You may have to take out the smaller cookies before the larger ones are done.
7. Cool. Allow cookies to cool for 5 minutes on the cookie sheet. Transfer to cooling rack to cool completely, about 20 minutes.

FOR THE ICING: 

Whisk the powdered sugar, vanilla and milk in a medium bowl. It should be thick. Too thick? Add 1/2  teaspoon of water. Too thin? Add 2 extra tablespoons of powdered sugar. You’ll know it’s right if you can drizzle the icing on a spoon and it holds for a few seconds before dropping back into the bowl.