To follow up:
Re-read Ianiceman's post...saw that he was referring to a specific decade of checked coats, not just checked coats of past decades. So I should clarify that the boat is having an odd jacket that you really like but are struggling to come up with coherent combinations for. Anyway, here is mine, Sullivan and Woolley, 1965:
Found myself wishing I had a wool navy tie when I realized that I did, in fact, have one. Ended up going with donegal rather than flannel trousers and I think it worked...but the options are clearly very limited with this jacket. Tie, shirt, and pants...I struggle to match all of these with it. Really looking forward to getting it back from having the sleeves shortened.
Is Jacket vented? Release top button (unbutton) to open jacket up, less boxy...