My wife hates it when I use a double plastic bag for a carry on. She has her stylish leather etc.
We carry meds on also. In case the check in gets delayed.
Carry twice what you think you will need, and split it between your wife's carry on and yours. A major hub airport gets shut down for a few days, or the plane has a problem, and you'll come back with less medicine than you planned.
And TSA and airline folks have been known to steal from checked luggage - never pack anything valuable or important.