Nice collection you got. First I saw was what looked like a two-tone VC? then an AP Diver, now an AP ROO.
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.
Swap out jeans for black, charcoal, midnight, navy, or brown trousers; worsted or twill.
Keep sweater or swap for same style in black, charcoal, navy, or brown.
Match sweater/jumper to trousers or not. If not, keep a bit lighter in tone than trousers; e.g, charcoal or navy sweater with black or espresso brown trousers.
Stay away from burgundy trousers and sweaters, that jacket is too bold already. So, wear nothing that will pull a color out of that jacket, unless the color is navy or brown, the darker, the better.
Swap shirt for solid blue from pale to robin egg; possibly even French or Prussian blue, if sweater is black.
If shirt is pale blue, consider wearing a solid navy faille or grossgrain bowtie, but only if wearing a v-neck sweater/jumper. No sweater, no bowtie, but a black knit or Grenadine four-in-hand one instead.
In fact, if you do not wear the sweater, you must wear a black or navy tie; preferably knit or Grenadine, to tame that jacket.
Keep shoes the same or replace with black suede or calf; your call.
Let the jacket talk and keep everything else quiet by making everything else as monochromatic as possible, except for your shirt, which should be lighter than sweater/jumper.
In summer, try cream summer weight flannels with cream socks and white bucks. Change shirt to white or pale blue linen and wear with a black knit tie and a white Panama hat. If it is smoking hot, lose the tie and keep the hat.
Too bad the jacket lapels are not bolder with slightly lower gorge, then the jacket would be timeless.
Until you tire of it, rock it like a boss!!
Thanks for the heads up.
Since the jacket is already not "SF Friendly", black is the correct color choice.
It is way past time to appease the natives, and it looks like he is all out of bubblegum,