I'm not sure pockets were even invented when Jesus was around. I suppose he wouldn't mind you having a place to put your wallet/phone/tissues/forgiveness etc.
Let's be honest: Jesus is busy. That dude must be ruling over all tang up there in heaven. He's got a sweet ride, cash to burn, and a magnificent wiener set to seek and destroy saved pussy. I'll bet he's not too concerned with whether or not you go 'cargo shorts' today.
Short Answer: I can't say if Jesus is into fashion or not. I've always assumed he was a robe guy, which to me is more about lazy than trying to make a statement. Why bother getting dressed when you can just robe it? As for the convenience of many pockets, I can't see him having any sort of problem with it. As a carpenter, I'm sure he'd appreciate having a place to put his little pencil and some fruit roll ups and shit. Am I rambling, now? I don't know what the fuck is with this question. Did I just start two sentences in a row with the word 'as'? Jesus would fucking hate that. He likes fluid writing style. That I'm sure of. Like in the Bible when they list all the things you're not allowed to eat and what we have dominion over. That shit was tight. Am I still writing this? Feels like I'm only thinking it now. Like a bad dream. I've tried at every turn to make a blasphemous joke in this post and I can't find one funny fucking thing. You keep money in your pockets. That plus the money lenders at the temple or something? Fuck me.