How to keep shoes on

[Spixie33]

I can see how that would work but I would feel bad punishing the other 4 kids who are excited to be out. Not to mention...that the ones who strip are the ones who usually would rather be inside.
The kids in my group who are "outdoor-lovers" tend to stay dressed and the ones who are my fair-weathered kids only like being out when it's +20C or better are the ones who tend to fuss about their boots, hats, mitts and want to act like they are in a nudist colony.

[Lee-Bee]

Put their mitts on. Then over top put a pair of thick men's wool socks on all the way up to their arm pits. They shouldn't be able to get the mitts off and it should then slow them down to get other items off as they don't have fingers and thumbs free.

After doing this awhile they should get out of the habit of removing items. Then try them without the big socks and warn them they will go right back on if they remove an item.

[Suzie_Homemaker]

Maybe rather than play, they walk. Not need destination. Pretty hard to take off shoes when moving forward. As far as gloves go, thread on string through coat. Can use safety pin to fasten. If they take off, their hand get cold. That on them but string stop getting lost. And hat - request had that tie under chin from parent. And tie it on. Maybe after while of walking instead just playing, it break habit of undress.