In a medium saucepan, combine heavy whipping cream, orange peel, whole cloves, cinnamon stick, anise pods, and allspice berries. Heat over medium until it simmers gently, then remove from heat and let the mixture cool for 20–30 minutes.

In a separate saucepan, whisk together granulated sugar, cornstarch, and salt until blended. Add the egg yolks and whisk until smooth, then slowly pour in the whole milk, stirring continuously to avoid lumps.

Once the cream infusion has cooled, strain the mixture through a fine mesh sieve into the milk mixture you just prepared. Discard the solid spices and whisk the combined mixtures until uniform.

Place the saucepan over medium-low heat and cook while stirring constantly until the mixture thickens and just begins to boil, around 8–10 minutes. Strain the pudding again to eliminate any lumps, then stir in softened unsalted butter, vanilla bean paste, and brandy.

Pour the silky pudding into dessert cups or a single serving dish. You can either serve it warm or refrigerate it for at least 2 hours until chilled.

In a mixing bowl, whip the heavy cream, powdered sugar, and a pinch of salt together until soft peaks form. Gently whisk in brandy to taste.

Top each serving of Winter Spice Vanilla Pudding with a generous dollop of brandied whipped cream, and garnish with a sprinkle of grated chocolate or a twist of orange peel.