Make the simple syrup by combining the sugar, water, cinnamon sticks, and star anise in a small saucepan and heat on medium until the sugar has melted. Set aside to cool and infuse for 30 minutes.
Add ice to an old-fashioned glass, then top with the bourbon, simple syrup, pomegranate juice, and orange bitters. Stir and garnish with an orange slice and pomegranate seeds.
