How long have you had him? Has he had any time acclimating to this crazy fall we are having? not sure where you are in NY, but our horses here in the Fingerlakes have been wearing their turnout sheets more than usual for october. They also have turnouts.....but it has just been SO wet. I have a draft cross, and even he, who is really warm usually has needed it. WE are also on top of a hill, so we get more wind than most, so mine are blanketed in winter. How much depends upon the horse. My clyde cross never gets more than a midweight. Some of the TB's get heavy weights since their coats are not as thick.
So, if this is your guys first winter here, I would recommend a turnout, and then maybe a blanket. Depends on wind, etc. I also just like blankets on mine, so I don;t always have to demuddify them.
Too bad you don;t already have one. Your horse probably could have used it the last couple of days and this weekend!
Signature undergoing edits. Please standby.......