There’s an argument to say that most men’s dress sense is basically the same as what it was when they turned 30 ish, with the odd tweak. Hence, at 43 I default to good jeans (denim shorts in the summer), a plain sweater or hoodie and a pair of nice trainers (more often than not, Nike Air Max 90’s). Swap the trainers for some boots and the sweater for a casual shirt and I’m sorted for most occasions.
So I think TJ that you’ve got to make a conscious decision as to what you want to look like and what you will and won’t wear as most people won’t consciously make that change.
The Graham Hall look isn’t a bad start point, though clearly it’s not for everyone. And I don’t think it’s a million miles from what you wear now of the odd pic is anything to go by.