Assuming your are talking about running this on a RPi (and not an x86 PC running Debian with a Raspberry Pi Desktop), then I guess you could get NOOBS or PINN to do it with a manually configured SD card.
You could install Raspbian with NOOBS / PINN along with a Data Partition (If using PINN, you can use Matt Huisman's site
to customise the size of the data partition. If not, you would have to create your own data partition to be the same size as the Raspbian BOOT partition).
Copy your Raspbian Boot partition over to this data partition, so that it becomes your backup boot partition. Make any modifications necessary to change the kernel to a new version. Don't forget to copy any lib/modules over to the Raspbian rootfs.
Then modify /settings/installed_os.json to indicate to NOOBS/PINN that 2 identical OSes are installed using 2 different boot partitions, but sharing the same rootfs.
You should now be presented with a choice of booting the same OS but using 2 different kernels on 2 different boot partitions.
The only problem with this technique is that each time you switch from one boot partition to the other, you will need to modify /etc/fstab to mount the correct boot partition. You could probably do this with a startup script.
So yes it is possible, if a bit clunky.
(NOTE: The above is only a strategy and not a step by step tutorial on how to do it. Further acquaintance with how NOOBS/PINN works would be needed, but it's all available in the relevant documentation).