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Preheat the oven to 350°F. Lightly grease a couple of baking sheets, or line them with parchment.
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To make the cookies: In a large bowl or the bowl of a stand mixer, beat together the shortening and sugar until smooth.
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Add the buttermilk and vanilla, again beating until thoroughly combined. The mixture may look a bit curdled; that's OK.
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Weigh your flour; or measure it by gently spooning it into a cup, then sweeping off any excess.
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Add the flour, nutmeg, baking soda, and salt to the wet ingredients and beat until the mixture forms a cohesive dough.
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Drop the dough in balls onto the prepared baking sheets, leaving about 2” between them. If you have a scale, each ball should weigh about 27g; a tablespoon cookie scoop is just right for this task.
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If you want a cookie with slightly crisp edges, flatten them with the bottom of a drinking glass dipped in sugar. If you like a chewier center, leave them as is.
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Bake the cookies for 14 to 16 minutes, until they’re just beginning to brown around the edges.
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Remove the cookies from the oven and transfer them to a rack to cool; or simply let them cool on the pan.
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To make the frosting: In a medium bowl or the bowl of a stand mixer, mix the confectioners’ sugar, salt, and butter until just combined.
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Gradually add the vanilla and the desired amount of milk or bourbon. (Less liquid will yield a stiffer frosting that will dry slightly, making cookies easier to stack; more liquid will result in a softer, buttercream-like consistency, one that stays soft for several days.)
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Beat the frosting on high speed until fluffy, 1 to 2 minutes. Frost the cookies immediately; or store airtight at room temperature until ready to use.
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Storage information: Store cookies, well wrapped, at room temperature for three or four days; unfrosted cookies can remain at room temperature for up to a week. For longer storage, wrap cookies airtight and freeze, layered in waxed paper if frosted.