Your style seems to be more classic, dainty, with items streamlined, close to the frame. You rock the long and lean silhouette, with an accent on your femininity. I think you look stunning in all four pics, but I can also see how you wouldn't feel your best in 2 and 3.
The pants in 2 are a clear departure from your style, with their mannish leg cut, a a flat long waist that will purposely avoid showcasing feminine curves, anyway from where I see it. Their color means they are meant to be fun, but clearly the cut is not what you are into - so no fun. I would try either: to roll them, as you have cleverly done, and try with booties/pumps; or having them cut into a mid-calf crop, and have the legs taken in so they become cigarette. Also, I think I know what you don't like: the shortening effect of the color juxtaposition. Having your shoes and tee match, with this vivid color, tends to shorten the legs as the eye and brain reduces the distance between feet and waist.
In 3, you might be put off by the max-on-max. It was a very astute on your part to add the bright necklace, as it brings the eye upward. But the BF's shapeless nature doesn't do well with the vest's generous slouch. Swap it with a leaner jacket and you are in business!
(BTW this slouch-on-slouch look, especially with flats, is VERY difficult to pull off for anybody who is not build like Cindy Crawford. So actually, looking cute here, you are not doing too bad at all!)