Place the strawberries, vanilla, and sugar in the blender. Pulse until the strawberries are fine and juicy.
Add the ice cream and blend until smooth. If the shake is too thick, add the milk and blend again.
Crumble 4 shortbread cookies into the blender and pulse to combine.
To serve, pour the shake into two glasses, then top with whipped cream, toasted almonds, and a fresh strawberry. Garnish each glass with a shortbread cookie, or crumble the cookie over the top!