In a pint glass or iced tea glass (we're assuming 16 oz), add vanilla syrup and fill about 3/5 of the way with cold milk. Add ice almost to the top and pour espresso (2 shots would be typical) over the top. If you've done it right, the espresso will mix in only about halfway down without stirring. If adding whipped cream, add it here. Drizzle the top with caramel and enjoy.