1. Place 1 cup strawberries in a medium bowl and gently crush with a fork to help release juices. Stir in remaining 2 cups strawberries and 3 tablespoons of the confectioners’ sugar. Set aside to macerate at room temperature while you prepare the other ingredients, or until the strawberries have released their juices. Alternately, you can let the strawberries macerate in the refrigerator up to 8 hours before serving.
2. Add the remaining 2 tablespoons sugar and vanilla extract to the whipping cream and beat using an electric mixer until firm peaks form. Keep chilled.
3. Cut the brioche slices into rounds using a 3-inch round cutter.
4. To assemble: Place one brioche round on a serving plate. Spoon a little of the strawberry juices (from step 1) onto the round, then top with ¼ cup of the strawberry mixture and a large dollop of whipped cream. Place the remaining brioche round on top of the whipped cream. Repeat the layering with the remaining brioche rounds, strawberries and whipped cream. Garnish with fresh strawberry halves.