I actually agree with you Matt. I think a shorter 'fashion' shirt worn untucked would look good with a leather jacket. But part of my vibe here is deliberately that dorky, awkward aesthetic that is dadcore. I want to alienate young hip guys like you. I sure as hell can't dress as trendy as you do, and I wouldn't want to try. But OTOH some days I couldn't be fucked wearing a blazer and tie either.
I'd like to say TOJ and impress everyone but the jacket's actually from Zara. That said, it looks ok I think.
RE the shirt, yes it would be better if it was a popover. It is a pretty bright pink/baby blue tattersal check with a BD, so it's a bit more informal than maybe it looks in that pic.