Toast the pecans in a dry skillet over medium heat for 3-4 minutes until fragrant, then let cool and chop finely.
In a large bowl, beat the softened butter and ½ cup powdered sugar until light and fluffy, about 3 minutes.
Add the bourbon and vanilla extract, mixing until well incorporated.
In a separate bowl, whisk together the flour, salt, and cinnamon.
Gradually add the flour mixture to the butter mixture, beating on low speed until just combined.
Fold in the chopped pecans and brown sugar until evenly distributed throughout the dough.
Cover the dough and refrigerate for 30 minutes to make it easier to handle.
Preheat oven to 350°F and line baking sheets with parchment paper.
Roll the dough into 1-inch balls and place them 2 inches apart on the prepared baking sheets.
Bake for 13-15 minutes, until the bottoms are lightly golden but the tops remain pale.
Let cool on the baking sheet for 5 minutes, then roll the warm cookies in powdered sugar.
Once completely cool, roll in powdered sugar a second time for that classic snowy appearance.