For most ex-tomboys to escape what they think is too boyish, they try to go to the other extreme and go too girly. This is a mistake because that’s why you end up feeling uncomfortable since you’re not staying true to your true style. These are my suggestions:
For everyday, go with a t-shirt dress:
For going to the bar, you could wear the same dress, just dress is up a little with a blazer
or a necklas
Or even both!
For clubbing: I suggest something, short and fitted. What you want to avoid is looking like everyone else in the club wearing a skin tight black dress. I would go with somthing like this:
For nicer, but not formal, go with something classic you can accessorize. I suggest a nice solid color, or this is where you would go with a LBD. I suggest:
with a nice earring: