Line two large cookie sheets with parchment paper or Silpat.
Whisk together flour, salt, and espresso powder. Set aside.
Cream together sugar and butter until smooth and fluffy. Add vanilla extract and vanilla bean or paste, if using, and mix until combined.
Add in flour mixture, about 1/2 cup at a time, until flour is combined.
On a floured surface, shape dough into a large disk. Wrap in plastic wrap, and refrigerate for 30 minutes.
Preheat oven to 350F.
Once dough has been chilled, roll the dough out to 1/4 inch thickness. Use a cookie cutter of your choice to cut out the cookies, rerolling the dough scraps as necessary.
Bake the cookies for 15 minutes, or until they have browned slightly at the edges.
Remove from oven and let cool on a cooling rack.
While cookies are cooling, add 1/4 cup butter and chocolate in a small bowl. Microwave the butter and chocolate, 30 seconds at a time, stirring after each iteration, until the chocolate and butter are both melted and smooth.
Once cookies have cooled, dip the cookies halfway in the melted chocolate, and set on wax paper to cool completely.