You'll need to give Trico a total of 96 barrels. Each play have 48 total so after you collected every each one of them in one playthrough, you'll still need to play it again and collect all of them again.
After that you can pause and go to Options/Objects. There's an option there called Fine Featherpaint, just use it on Trico's body, holding circle like your shield, choose the color with up and down and paint the most of the body to make the trophy pop