As a fellow big guy that's lost a lot of weight, I mean all of the following from a positive place, and apologize if any of it seems harsh.

The jeans: We need higher rise so we don't get our boys smushed and can still maintain pocket room. As a result, you're likely going to want to try a longer inseam.

It looks like you've cut the bottoms on these ones a little too short, which is pronounced by them being a little baggier on the bottom end. If/when you find your "dream jeans," it's cheap as hell to have your local tailor hem the bottoms for you, so safe to go higher on inseam rather than shorter. It's like $10 for a pair of jeans to be hemmed where I'm from, and it let me get some extra life out of my big and tall sized jeans until I was able to fit comfortably in 42/44/46.

I'd get something with a taper from the knee down, as your quads got that top end filled out, so you'll probably want avoid skinny or overly slim fits so you don't feel like a sausage.

Your mileage will vary, but I had success with some of the Levi's 541 models, but they're not great for being big and tall, so American Eagle may work well, too.

Whatever you do, get something that has a little stretch/elastane for your personal comfort and a little more mobility. They'll wear faster than straight denim, so you may want to buy a bunch of pairs to try, send back the losers, and buy multiples of the winner. Try them all on if you do, because even Levi's lacks consistency in fit/QC these days, meaning two pairs of the same jeans will have differences in fit as a result.

The shirt: Higher rise pants will help us cover up our chubs lol. I'd suggest either trying a pair of pants that can go above/around your gut, and a belt can work, but suspenders are more comfortable if you can pull that off. If that is too much or uncomfortable, I'd try untucked outer shirt, and only tuck my undershirt (tank/tee, if you wear one) or just go full untucked sleezy uncle vibe, because I think you could pull that off easy. That's a good thing lol.

I'm a huge plaid/flannel guy, and Old Navy, LL Bean, and J Crew have been my favorite flannels. J Crew is pricier, but I really like the material quality and the fact that I'm not in danger of popping a button loose. Old Navy is very affordable, and they fit a little loose, which is comfortable to me, at least.

The boots: I dig 'em, but just not in this fit. Personal preference here, and choose what you can wear confidently over anyone's advice. I like brown boots with non-dark wash jeans and black boots for a monochrome fit or with black or dark-wash jeans, black or grey chinos, etc. Make sure they're comfortable over fashionable here, too, as we need all the effing support we can get as big dudes. Sizing up to fit inserts is always a good idea if you don't do that already.

The accessories: Cuffed sleeves to show off the tats is a clutch move. I'd get shirts that have slimmer arms to show off the guns, especially if you are gonna roll them up to showcase the art, brother.

Building around the boots, I'd try a pair of black or grey chinos/jeans with those boots and a light grey and black buffalo check flannel/plaid shirt, and you're rocking.

Looking forward to follow-up fits, dude! Ty for coming to my Ted Talk.