If you’re dealing with an inveterate nudist, buy articles of clothing that are difficult to remove—zippers and Velcro may be easy to get on, but they’re also easy to take off. Go with lace-up shoes (and double knot them) and button-up coats and shirts. Purchase “onesies” that button under the crotch.
Teach your child how to put on his own clothing, and then praise, praise, praise him. Telling him how proud you are and “what a big kid” he is goes a long way as an incentive.
Tell him he has to wear his hat/coat/gloves when you reach your ultimate destination, but that he can take them off in the car before you get there. This allows your child to agree to your demands with dignity and a feeling of independence.