From the inside out
I don't own a lot of dresses. I have maybe four that I will occasionally wear because they are comfortable and the right length but otherwise most of the time I am either in skinny jeans, skirts or shorts. That also isn't about to change either as I like being ready quickly and out the door. Primping excessively isn't for me and if I take more than 15 minutes from dressing to light makeup application to shoes I feel I am doing something wrong.We morph over the years from an awkardness to a balance of practicality and style because we must and anyone who has tried to walk in stilettos for an extended period of time will understand this. Eventually we adopt a style that mirrors a genetic woman's while realizing that they themselves are not all the same. For myself I have settled for a blend of feminine and practical which took some time to fine tune and which works very well for me.
Your journey will be unique to you but I would suggest that it might best be undertaken from the inside out instead of the other way around