My sims will not change into Outerwear no matter what I do. They go outside when its cold in whatever and don't change, then they get the teeth chattering moodlet
I try to force them via the chest of drawers, but all it does is the change animation, but doesn't actually change the clothes.

Is there something specific that could be causing this?

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Have you gone through the above, to rule out an out of date mod?

Hello, I'm just here to help in the event that you (or future people who find this site with a similar problem) have yet to find a solution. Upon narrowing down all potential problems, I discovered that that whiterider's mod that reduces/eliminates curfew for teens and children created the issue for my particular case. It's likely because it has yet to be updated for Seasons, but in any case, remove it from your game and see if that helps. I know that I'll be waiting for an update of that mod, and I hope this helps!