Love the new jade dress on you, great shape. I recently picked up a pink dress similar in style to this one from Express.
I think you are too hard on yourself, I adore your style. Your outfits always have something going on, be it in layering, prints, or silouhette (dress one day, shorts the next).
I have been trying to branch out of my own rut and recently picked up a maxi dress (yikes, I'm petite!) and cobalt cropped trousers. I'm in the middle of house purchasing but will try to snap and post picks when I can soon.