honestly I don't think Ervell is going to work for you.
edit: I mean, bomber is ok, but Ervell as a look probably not for you
Elisix, I know you've got a lot of gear, but you'd probably be better off going mtm. Medium height, broad chest and shoulders... most all your old untucked fits are long in the body. If I remember correctly, you always used to roll up your sleeves, and I'm guessing that was because they were too long. Chinos, plaids or oxfords or tees, and baller-basic footwear should not be hard to pull off, but if your tops don't fit, they don't fit. Extensively tailoring a $300 kitsune plaid seems like the wrong way to go.