In a medium bowl, whisk together flour, baking powder and salt. Set aside.
In a mixing bowl, beat butter and brown sugar until light and fluffy, about 3 minutes. Add egg and vanilla and continue beating until well combined, scraping bowl as necessary. Gradually add flour mixture and mix until fully combined.
Spread a couple of sheets of overlapping plastic wrap on your work surface to create an area large enough for you to roll your dough. Take half of the dough and gather it into a ball.
Roll the dough between the two pieces of plastic wrap to desired thickness. Occasionally lift the plastic wrap to release any wrap that gets caught under the dough. I roll mine to just under 1/4". Roll it thinner for a crispier cookie (about 1/8") Repeat with the other half of dough.
Remove top layer of plastic wrap and use flour dipped cookie cutters to cut desired shapes. I dip the cutter in flour in between each cut or two. Gather dough together and reroll to cut more cookies. I rolled my dough between the same sheets of plastic wrap so I didn't need to add any flour to my rolling surface.
Place cut out cookies a couple of inches apart onto an ungreased cookie sheet. If topping with raw sugar, sprinkle on generously before baking. I baked a portion of my cookies topped with the raw sugar and left the rest plain to ice later.
Bake for 8-12 minutes. Time will depend on how thinly you rolled your cookies and how hot your oven runs. I baked mine for about 8-10 minutes or until the bottoms edges were just beginning to get very lightly browned.
Allow to cool on baking sheet for 5 minutes, then remove to a rack to finish cooling.
Melt butter in a small saucepan. Stir in brown sugar and a nice pinch of salt. Add milk and bring to a boil, stirring frequently. Allow it to boil for about 30 seconds, then remove from heat and allow to sit for about 10 minutes. Get your cookies ready to decorate and your toppings ready to go.
After the 10 minutes of cooling, whisk in the vanilla and the confectioner's sugar until icing is smooth and creamy. Add more milk, a teaspoon at a time until desired drizzling consistency.
You can either drizzle the icing with a fork or spoon it into a zip top bag to pipe it. If you use the bag, just cut one of the bottom corners off. (I used the bag.)
Working quickly (because icing will continue to thicken in the bag) drizzle the icing over cookies, stopping to add sprinkles or nuts immediately after you drizzle each cookie. Allow icing to set firmly before storing cookies.
*The amount of cookies you get will depend upon the size of your cookie cutter and how thinly you roll the dough. This recipe made about 52 cookies for me.
*The icing sets up quickly so don't make it until your cookies are cool and you have them set up and ready to be iced.
*If your icing begins to get too thick in your piping bag, you can add a splash of milk to the bag and massage it into the mixture until it's fluid enough to drizzle again. I used a binder clip to fold over my snipped corner and close it off while I was mixing in more milk. I think if I weren't also taking photos, I would have been able to ice all of the cookies without having to thin the icing again.
*I like to roll my cookie dough between sheets of plastic wrap right after it's been mixed. It's cleaner and easier to work with. This only works well if your plastic wrap sticks to your work surface. You can also just wrap the ball of just mixed dough in plastic wrap and refrigerate, then roll it out on a floured surface and cut out your shapes as you traditionally would with sugar cookies.
*I rolled my dough between an 1/8" and 1/4" thick and baked for 8-10 minutes until lightly golden on the edges. This gave me a firm, but soft cookie. For a crispier cookie, roll thinner and bake longer.
**Store cookies in an airtight container remembering that icing will help keep the cookies soft. Mine were still soft on day 5. It's more difficult to keep them crispy since any topping with moisture in it will soften them. If you're only topping with sugar and you rolled and baked them using the crispy tips I've provided, I would store them in an airtight container layered with paper towels to help absorb any excess moisture. Please note that this recipe isn't engineered to bake up super crispy cookies. The different methods simply offer you an option to go a little crispier or a little softer.
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