Prepare the berries by slicing larger strawberries and leaving smaller berries whole. Toss all berries with 2 tablespoons granulated sugar in a bowl and set aside for 30 minutes to macerate.
In a large chilled bowl, beat the heavy cream, powdered sugar, remaining 1 tablespoon granulated sugar, and vanilla extract with an electric mixer on medium-high speed until stiff peaks form, about 3-4 minutes. Set aside.
If using, drizzle the berry liqueur or orange juice over the cake cubes and toss gently to coat.
Begin layering in a 3-quart trifle dish or glass bowl: spread one-third of the cake cubes on the bottom, followed by one-third of the vanilla pudding, one-third of the macerated berries with their juices, and one-third of the whipped cream.
Repeat the layering process two more times, ending with whipped cream on top. Use a spatula or piping bag to create decorative swirls on the final layer.
Garnish the top with reserved fresh berries and mint leaves if desired. Cover loosely with plastic wrap.
Refrigerate for at least 4 hours or overnight to allow the flavors to meld and the cake to absorb the berry juices.
Serve chilled by scooping through all layers with a large spoon to ensure each serving has cake, cream, berries, and pudding.