At left is The Empress from The Illuminated Tarot. It's my favorite version of The Empress, I think because of the stars! The Empress is often shown as a pregnant woman, although one can't be sure of that in the Illuminated version.
She is meant to represent not so much fertility but the ability to provide, nurture, and manage.
I associate her with the suit of Cups because of her loving, mothering nature. Not to mention that as a fertile female she represents the divine vessel--and if the cup isn't a vessel, what is it? I also associate her with Mother Nature.
Like The Emperor and the Priest, she can represent authority, institutions, the medical field, or education. But I always see her more positively than the Emperor or the Priest.
I see her as a good omen of prosperity, health, or fertility. A keyword that comes to mind when I see her is "comfort." Doesn't she look comfortable on her cushions under the night sky?
In the negative, she may represent issues with a mother figure or with an employer--not necessarily female. She could represent emotional disturbance or physical loss (disability, health). She can represent someone(s) who are overbearing, perhaps over-mothering. She can represent losing touch with nature or a need to take better care of the kids/home/spouse/self.