Adrianna Papells midi cocktail dresses are a great example of this balance
While the skirts slightly swayed and bobbed at every step of the wearer, the crinoline beneath could be easily lifted up to gather it up to one side to fit through a narrow doorway or into a carriage, or folded to allow the wearer to sit down (imagine it like a modern throw tent, stable but also flexible)
Y2K is also a little nostalgic for before its own time
The square neckline and sculpted bodice are lovingly hand-gathered for a flattering fit, while three dainty handmade bows trail across the front like notes in a bridal symphony
If you love the look of Old Navy's LBD, it also comes in a taupe color, which looks just as good and just as versatile.
Once you feel good in that, experiment with dressier options