I'm doing my own makeup, it needs to be theatrical but there are two themes (The classic Cinderella we all know, and then SINderella which is meant to be the same- with a twist.  So a bit darker.  Both are fantasy and will be manipulated.
The outfit is blue  (as shown below).  I have very light olive skin.  I need to know what style of makeup will do.  For the classic I want it to be naive and simple yet noticeable.  For the darker version, it can be a bit more free style.  I have everything, and glitter as well (different colors).
Also, it comes with a crown.  So... Hair up, or down?

Thank you!

My first suggestion is to always check with the photographer provided that he or she needs the images to be useful for their port as well. In the event that they've given you free reign then hair and make-up are going to depend more on what looks you want to showcase, your skill level, and what the ultimate end goal of the shots is e.g. publication etc.

Thank you!  The photographer  has given me a free hand (both hair and makeup).
As for what I have in mind, as I designed the session through and through, I want a Cinderella with an edge, i.e- some will be the classic one, but the more challenging one will be to create a Cinderella with my own saying- a little less naive, a bit more mature.  As for my skill level, as a model I have about eight years of experience, so I would say I am at lest fair.  My makeup skills are also good.  This may require two different sets of makeup.  Does that answer your question?  -Thank you!

Noting that you've been free reign and you have some experience then my suggestions are as follows:

Cinderella: Keep the first look clean and fresh with lightly dewy skin and a nude gloss on your lips. Based on the wardrobe you've shown for this look I'd avoid any dark make-up. In terms of your hair, the classic Cinderella style updo is fitting.

SINderella: Based on your first post I'm unsure if you're meant to be keeping the dress, or wearing the top shown below. Either way it may make sense to just do a darker gloss on your lips and tousle your hair.

Personally, I'd avoid glitter for both looks. While it can be beautiful it can also be tricky to work with. If it's too light it looks accidental and if it's too heavy it can veer into stripper territory.

Perfect-
Thanks!