Thanks for looking at this long photo essay! And I appreciate your discerning eyes. I hope it might be some value for others to see this as well.
Here is my take on the pics:
I wear jacket #1 and #2 more often than my other jackets, and wear them most often of all with trousers. These are the jackets I tend to wear with jeans. I had worried that #2 might be too short for trousers, since overall it just hits my belt (similar to the jacket that Aida was wondering about) but in looking at the pics, I think those angled points make it work quite well with trousers even though it is shorter.
I ALSO wear these two jackets with dresses and skirts. Vix, I take your point they might be a bit long or boxy. However, I tend to wear them with a pencil skirt that has a fitted high waist, and I THINK it works (though I ought to take some more pics to be certain).
I would NOT wear with a full skirt.
Jacket #3 (collarless jean jacket) is a puzzle to me. I find it a bit tough to wear (although as jacket-twin Claire has pointed out, it might be better as a spring/summer piece.) Also, it's a little bit big for me, so that might contribute to some discomfort. But my daughter liked it best of all when she was doing the photos. And in a way I can see why. Its intermediate length makes it "okay" (if not great) with both pants and skirts. In that sense, it could be a very useful piece to hold onto.
Jacket #4, the faded jean jacket, is one I pretty much like to wear with skirts and dresses, but I will also wear it with low contrast tops and trousers. I really don't like it with the high contrast tops.
Jacket #5 is my least worn jacket. It's really exclusively a skirt/dress jacket, and I don't particularly like the colour/fabric with the colours or fabrics in my current fall/winter wardrobe, so it just doesn't mesh all that well with what I have. At the same time, I love the raspberry red. I think I would like it a lot better with lower contrast outfits.
Thanks again, those of you who looked and commented or just had thoughts about this.
I really think the point about contrast is key.
And Claudia, thanks for the link to the rule of thirds by Imogen; it's excellent. And I take the point that the length of the skirt (or bottom) will make a big difference to what length jacket will work. But I also think the shape of the skirt is relevant, and I still think body type is an important consideration, because some looks simply won't work as well on some bodies. So you might be following the rule of thirds but still look "off."