Pour the water into a medium-sized saucepan and set over medium heat. Stir in sugar, and when dissolved, add dried figs. Remove from heat just as mixture begins to boil. Set aside to steep for 30 minutes, then strain into a clean jar and chill, reserving the plumped figs for another use.
Set out two Collins glasses. If desired, press sliced figs into the sides of the glasses for visual effect.
To make milkshakes, combine Chameleon Cold-Brew Black Coffee Concentrate and fresh figs in the pitcher of a blender. Blend until mixture is smooth, but still has a few flecks of fig. Add ice cream, fig simple syrup, and rum, and blend just until combined and creamy.
Pour milkshakes into glasses and garnish with whipped cream and a fig slice. Serve immediately.