Spread the shredded coconut evenly across a dry skillet set over medium heat. Stir frequently to ensure even toasting, continuing until the coconut becomes golden and emits a nutty aroma, roughly 5 to 7 minutes. Once toasted, transfer to a plate to cool completely.
In a small saucepan set over low heat, add the soft caramel candies and milk or cream. Stir constantly until the mixture is melted and smooth. Remove from heat, then blend in the vanilla extract and a small pinch of salt.
Add the cooled, toasted coconut to the warm caramel mixture. Stir thoroughly until the coconut is uniformly coated with caramel.
Line a baking sheet with parchment paper. Using a small cookie scoop or a rounded tablespoon, drop spoonfuls of the coconut-caramel mixture onto the sheet. With lightly moistened fingers, press each portion into a circular, flattened cookie shape.
Place the chocolate chips and coconut oil (or butter) in a microwave-safe bowl. Microwave in 20-second bursts, stirring between each, until the chocolate has melted fully and is smooth in texture.
Dip the base of each cookie into the melted chocolate, then return it to the parchment-lined tray. Using a spoon, drizzle the remaining chocolate decoratively over the tops.
Refrigerate the tray for 15 to 20 minutes or until the chocolate sets completely. Cookies may be stored in an airtight container at room temperature for up to three days, or kept chilled for extended freshness.