Too many choices can be overwhelming for young kids IMO.
Of course it can. If you saw my example, you should have seen that he choices are usually limited, by me as to things which are appropriate and to prevent them being overwhelmed - do you wan time to buckle you in, or do you want to try yourself? PJs on first o brush your teeth first?
With regards to the being cold thing, I don' wait until they are shivering - before we go out we look out of the window, check the weather. They are encouraged to consider what might happen if they go out in cold weather without a coat/ jumper/ trousers etc. I explain that we wear warm clothes in cold weather. And yet, sometimes despite all this, they still want shorts - sometimes they will agree to wear tights or leggings under the shorts, other times not. 9 times out of 10 as soon as we step out of the door, DC will say "it's cold, can I change my mind?" and of course they can! They don't wait to be blue and shivering. If they don't mention it, I check in with them- would you like your coat? how are you feeling? Don't fore, I've brought warm clothes if you would like them...etc etc.
So instead of hoping it will be automatic as they get older, I'm assuring that they understand WHY we wear warm clothes when it looks cold outside, what 'cold outside' looks like, other than me just 'knowing', so they know the WHY behind the action in the hope that as they grow up, they can take the WHY and apply it to other situations.