Warning: Spoiler! (Click to show)
First fit: I'm lukewarm on ballcaps, but whatever that's my opinion. The W+H shirt would look great one size larger. You're built enough that you'd probably do better sizing up to get a little more breathing room in the chest. I've never liked the toe detail on JPs. Again, personal bias, but I think Stan Smiths or just white Vans would work better. I don't mind the micro-cuffs on the jeans (which fit really well, by the way) in this context.
Second fit: The awkward roll (cuff?) on the overshirt sleeves looks, well, awkward, and I'm sure the position of your arms isn't helping. I assume it's some kind of heavyweight chambray or denim? Maybe the picture isn't capturing it very well, but it looks all crispy and new here. It'll look way, way better once it's been through a few bar fights, had some beer spilled on it, that sort of thing. A v-neck would probably work better than the crew-neck you're wearing, but that's a minor point.
The main issue I see is the shoes. This fit would improve drastically with a pair of lace-up shoes or boots. I'm pretty sure you've posted fits with Aldens or something of that ilk, and they should be swapped in for the JPs post-haste.
tl; dr: First fit: size up on shirt. Second fit: fix shirt sleeves, swap out sneakers for boots/shoes.
I usually do wear Aldens, but was kicking it in my mother in laws yard with the kid day 2 so I kept em on...my son was literally running around throwing pieces of dog shit at my daughter...I know, I'm a lucky guy.
The second pic, shirt is denim, wore it again today and its not stiff at all, bought used and its soft as hell. Wore my Aldens today:
hats are cause my head gets damn cold.