Thank you all so much for your thoughtful comments.
I've been mulling some more about it myself. And here's what I think.
I think RACHYLOU is right. In the sense that neither of these outfits is especially "me." Or ideally "me." Or something.
In the past year, I've been trying really hard to collect wardrobe items that work well for my casual life. Things I would actually wear -- not just things that expressed my style perfectly, but might go sitting unworn in my closet.
The problem is, my actual life demands comfort, which includes an element of softness (especially in winter).
But my preferred style is, in fact, more "crisp" or structured.
This puts me in a bind. The outfits that are most personally expressive are also the outfits that I'm not comfortable wearing for my work-at-home life. My "crisper" items -- like button front shirts, jackets, tailored trousers -- go unworn for long stretches of time unless I am travelling to the city or working there.
In summer, I can wear them more often and more easily, because the weather calls for them.
Outfit 1 was more than appropriate to the occasion. I was extremely comfortable in it, both physically and socially. (One of the other presenters was wearing a virtually identical outfit.) The "shortness" of that skirt doesn't bother me in the least, to be honest. In fact, it doesn't even feel "short" to me, worn like this with tights. So I will respectfully agree to disagree with those of you who feel it is still "too short." It would be, in a corporate setting, or if I were a different kind of person -- but for me, worn to this kind of event, it's not.
The long, straight, vertical lines of this outfit helps make it feel slightly more "me," perhaps, than Outfit 2. But overall the outfit is too soft for me. And not "dynamic" enough. There is something missing.
Outfit 2, to my mind, HAS at least some of the dynamism that outfit 1 lacks. At the same time, it remains a bit too soft/ slouchy for me. And I wouldn't be comfortable in the butt-vest.
So. How to combine dynamism with the softness I require in my winter? That is a new question.