Preheat the oven to 350°F and spread the walnuts out on a baking sheet and bake for 10 minutes to toast them. Set them aside to cool while you prepare the rest of the recipe.
In a large bowl or stand mixer fitted with a paddle attachment, beat together the brown sugar, butter, and mashed banana at medium speed for 3 to 4 minutes.
Reduce speed to low and add in the oil and eggs, one at a time, then add the vanilla and mix until fully incorporated. Scraping down the sides of the bowl as needed.
Add oatmeal to a food processor and pulse until fine to make oat flour.
In a medium bowl, whisk together the oat flour, flour, baking powder, baking soda, salt, and cinnamon.
Fold the dry ingredients into the wet ingredients just until combined.
Fold in the chocolate chips and toasted walnuts.
Cover the mixing bowl in plastic wrap and refrigerate for at least 12 hours and up to 3 days before baking. DO NOT skip chilling as this is where the signature banana bread flavor develops.
When ready to bake, preheat the oven to 350°F and line a baking sheet with parchment paper.
Use a medium cookie dough to portion out the dough and drop onto the prepared baking sheet about 2 inches apart.
Bake for 10 to 12 minutes then remove from the oven and allow them to cool for 10 minutes on the pan before transferring them to a wire rack to cool completely.