To make the simple syrup: combine the sugar and water in a saucepan over medium high heat.
Stir until all sugar is dissolved completely.
Add in the vanilla extract, stirring until combined.
Turn heat off and allow to cool.
Fill two mason jars (or coffee mugs) with ice.
Pour 1 cup coffee into each jar/mug.
Add desired amount of simple syrup to each mug. *I use about 1/4 cup in each
Add 2 tbsp milk to each mug and stir well.