Me to my 3.5-year-old boy after evening bath (winter here right now): Your feet are going to get cold, don't you want to put on your slippers to keep them warm?
Him: No!
And if I put them on he'll take them off as soon as I'm not stopping him from doing so.
For putting on warm enough jacket for school I try similar reasoning which has yet to work with any kind of consistency, still mostly lands up having a bit of a tantrum all the way until I hand him over to his teacher.
His two-year older sister was a lot less difficult at his age.