Situation 1: you're just cold enough to want a sweater if you had one, but it's ok that you don't.
Situation 2: you're just warm enough to take off a sweater if it was convenient, but it's ok that it's not.
This is an example of a broader question...
I'm writing this before any answers come in, so I don't know for sure what people will say. But I've asked this question of many people. Some people (though not very many!) don't have much of a preference and argue with me about how if both options are uncomfortable, then why is one better than the other? But most people I ask know that these two experiences are quite different forms of discomfort, and prefer one over the other. I tried to phrase the question in this survey with the example of wanting to take a sweater on or off, in hopes that I could communicate the intent of my question.
Generally I find that more people prefer to be too cold, but the results don't seem to be too far from evenly split. People who prefer to be too cold often like how it helps them feel alert, or dislikes the way being warm makes them sweat or feel lethargic. They also talk about how "you can always put on more clothes to get warmer" (which is sort of cheating, because then you're not too cold anymore - but I think it makes being too cold more comfortable because it usually feels easier to escape). People who prefer to be too warm often find it a relaxing sensation, like being in a hot tub.
I will always prefer to be too warm. Being too cold reminds me of tension and anxiety. I've written about this and talked about it a lot with friends and complained about being cold many times.
I'm curious to see what people will say here!