Preheat the oven to 350. Leaving the skin on, slice the potatoes into wedges and arrange on a baking sheet covered in parchment paper or foil. Make sure they aren't touching. Massage all the wedges with olive oil. Sprinkle with salt and pepper and roast on the middle rack until they just start to brown, about 20 to 30 minutes. Remove from the oven and sprinkle with the asiago and return to the oven to finish browning for about 10 minutes or so. Sprinkle with truffle oil just before serving.