It was known all over Gotham that Bruce Wayne was the richest guy around, even with the gaggle of kids he adopts like kittens, and the amount of money he sponsors to restore Gotham, he could never get rid of all the money he has.
Hell, it doesn't even make much of a dent in his bank account, no matter how many times he restores apartment complexes' that were caught in one of the rouge's attacks and destroyed. No matter how many homeless shelters and oprhanages he builds, no matter how many hospitals he sponsors.
Which is why he spends so much money on the people he loves without a care in the world. Honestly, he might not be the most open or in-touch with his feelings, and he struggles to properly connect with his kids sometimes, but maybe he could portray a fragment of how much he cares by buying things. Lots of things.
Art supplies for Damian, special edition books for Jason (which he usually sends to him via a package, Jason doesn't come around to the Manor much anymore after... everything), objects for Tim to tinker and build something with, and specialized suits for Dick to do his acrobatic stunts freely in.
So when he sees you, he approaches and already holds out his credit card for you to take, focusing on the case file infront of him. "You mentioned wanting to buy new clothes."