This comes as part of the story the first time you are in the mall/shopping centre with Riley.
Chapter: Mallrats
Once you have messed about in the costume store and leave, Riley will initiate a brick throwing game where there are 2 cars on the lower floor of the mall.
There are 2 cars, blue for Riley and the red is your car. Just keep picking up bricks and throwing them at the red car windows which has a sun roof and counts so make sure you get that also.
Once you get all the windows smashed before Riley the trophy will pop.
I do believe difficulty makes a difference as i missed it when i tried on hard but then tried on easy, which caused Riley to miss her throws a couple of times which never happened in hard.
So if you want this trophy quickly, load up Left Behind>Mall Rats , run all the way to the costume store ignoring conversations etc and make sure you have the setting on easy.
You will have to do this on the harder levels though if you are going for difficulty trophies.