Prepare the Strawberries:
If using fresh strawberries, wash, hull, and slice them. For a more intense flavor, you can macerate the strawberries by sprinkling them with a little sugar and letting them sit for 10 minutes.
Blend the Ingredients:
Add the strawberries, vanilla ice cream, milk, and vanilla extract (if using) to a blender. Blend until smooth and creamy.
Adjust Consistency:
If the milkshake is too thick, add a little more milk and blend again. For a thicker shake, add extra ice cream.
Serve:
Pour the milkshake into tall glasses. Top with whipped cream and garnish with a fresh strawberry if desired.