I missed this thread yesterday, so I'm late here, but I wanted to chime in anyway. First of all - you have a terrific jacket there. It is basic, which is a splendid thing in my book, because it is pretty timeless. The fit is perfect, as already stated by the boss:) I really love how you've styled it already, particularly in #2, (also stated many times already, but a good thing...).
You've seen my thread with denim and dresses/skirts, and I guess it is a bit different to wear denim jackets like that than paired with jeans. To me, a pair of tight jeans would be problematic to wear with a fitted, cropped denim jacket, too, since I would feel too body conscious and my pear tendencies would be enhanced. I suggest working with the silhouette, no matter if you wear pants or skirts. A roomier fit at the bottom plays very well against the smoother fit on top. Do you have any baggy boyfriend jeans or tapered pants? I also suggest trying to wear the same color under the jacket as in your pants (unless they are denim, of course). Try the turtleneck or another fitted top in matching color, that gorgeous belt, wider pants, and I think you'll find that your shape is enhanced in a very good way! You DO have a very nice one.