In the junkyard, eventually you'll see an area full of things to Smash.
You will first want to smash the Sign.
Then smash the cans of red paint.
This will create a splatter of red on the sign's cute girl face and an option to Graffiti.
Graffiti the girl's face and you'll get this trophy!
NOTE: The order of actions I listed is important, otherwise the paint won't land on the sign.
Also, don't save this for last. Smashing the mannequin, toolbox, and junk box will move the scene forward and you'll miss this completely.
You can come back to this via Collector Mode after completing the episode but there will still be cutscenes to play through before reaching this section. It won't jump to smashing directly.