In a large bowl, use an electric mixer to mix the butter, oil, and brown sugar for about 2-3 minutes. Add the egg and vanilla and mix for another 2-3 minutes. Add the cinnamon, baking soda, baking powder, salt, and flour and mix just until combined.
MAKE THE STREUSEL
Combine all of the streusel ingredients in a small bowl and mix together with a fork. If the mixture is too sticky/not crumbly, add a little more flour, 1 tablespoon at a time.
SCOOP & TOP THE COOKIES
Use a large cookie scoop to scoop the dough onto a baking sheet lined with parchment paper or a silicone baking sheet. Use the back of a tablespoon to press a slight indentation on top of each ball of dough.
Sprinkle some of the streusel on top of each indentation. Bake the cookies for 10-12 minutes or until just barely golden brown on the edges. Let the cookies cool for a few minutes on the baking sheet before transferring to a wire rack to cool completely.
MAKE THE ICING
While the cookies are baking, make the icing.
Whisk the powdered sugar, milk, and vanilla together in a small bowl. Drizzle the icing on the cookies while they are still warm (immediately after transferring to the wire rack).