I did this recently to revive to an old IBM laptop (an N33sx/16, i.e. pre-Thinkpad) with a dying floppy drive. I had two Zip drives, one USB, one parallel, so was able to transfer from a modern PC once I managed to install the DOS driver for the Zip drive via floppy.
Of course it helped that there was still a functional DOS on the laptop from many years ago (DR-DOS 7.03 FTW!).