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My son was big, too, for his age (still is), at around 20 months the last diaper size was coming undone when he was active or bending. So we switched to pull-ups. Had to buy size 3-4 pull-ups right away (Huggies were the best, though we had used generic diapers). He had these pull-ups (which I tore apart at the sides while he was laying down, just like diapers) until 26 months old, when we started potty training cold turkey. Pull-ups were a bit more expensive, but not that much, since he was holding for longer intervals than a baby.
I did try to train him at 18 months, and he had no interest or discomfort running naked for 2 weeks, so I put it off for later.
If I had a baby again I'd use cloth diapers where you can sew any size you want (the environmental thinking kicked in since), you may want to try them.
On the side note, if you want to have a peek into the future - my son is a month shy of his 4th birthday, and wearing size 6 sweaters and pants (I have to shorten the legs though). Shirts are still size 5. I had those nice preppy shirts bought long ago for school, size 5, have to sell now - he's 3, still a toddler in his mind, no way he'd be comfortable in those plaid brand name shirts, though they are his size right now. A different set of problems with big boys :)

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