So I decided to broach the subject with him, instead of showing him the boots and getting laughed at to my face.
Me: It's going to start raining soon.
Lucas: I know, look at those clouds mommy.
Me: You'll need rainboots soon. Would you like Curious George rainboots?
Lucas: Mommy, did you see the boots that Gianluca has, in my class? They have fire on them.
Me: Yes, I've seen those. They're pretty neat.
Lucas: Yeah, they're red with fire on them. Me: So, you want those?
Lucas: Yeah, those are the ones I want.
I didn't even bring up umbrellas, since I also got him the matching CG one too. I guess I'm making a return soon.