Combine milk, strawberries, and strawberry ice cream in a blender. Blend on high until smooth, about 1 minute.
Drizzle 1 1/2 teaspoons strawberry syrup on the inside of a glass jar. Pour in milkshake. Garnish with whipped cream and remaining strawberry syrup.
Take reserved strawberry and carefully cut at an angle but do not cut completely through. Place strawberry on the rim of the glass. Insert a straw and enjoy!