Place the apple cider, cinnamon stick, orange juice, cloves, and star anise in a small pot and bring to a boil. Lower to a simmer for 10 minutes. Remove from heat and strain into a pitcher.
Rim the glass with sugar if desired.
In the glass, add 2 oz bourbon and 1 cup of the cider mix.
Garnish with an orange slice and a stick of cinnamon and serve warm.