You are going to have to lose quite a bit of weight to go down to size medium in jackets and shirts. I was close to 220 6 months ago and I was wearing shirts in size XL and size L. Now at 190, I can wear size L easily and can squeeze into some size M, but to properly fit size medium I figure I would have to go down to maybe 170. Its hard to say exactly as sizes are not consistent across brands such that one company’s size M is another’s size L. On the Big Deborah does Dallas shirt and I will buy this waist sizes its a different story. At close to 220 I was wearing size 38, now 30 pounds later at 190 I am at size 34. They say on your waist every 10 pounds is one size. My guess would be 3XL or 3XLT. Depends on if he has a long back and/or a large tummy that would take up the length of the shirt. The tall size would give him more length if he needs it. I see a lot of chubby guys walking around with their bellies hanging out because they didn’t buy a shirt long enough. That being said, 300 lbs is a bit overweight. If you can find a shirt measured generically as medium, large etc., then go for extra large.
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