1. Pour all ingredients into a mixing glass.
2. Fill the glass with ice and stir.
3. Strain into a coupe glass over a large sculpted ice cube.
4. Add a splash of orange bitters onto the ice cube.

* Simple syrup is equal parts sugar and water. Dissolve sugar with water in a saucepan over medium heat. Add vanilla to taste. Strain into a sterilized jar and seal tightly with a lid.