Another Update! I've spent a while mulling over the character and trying to understand the characters 'feel' materials and mechanics wise. To give context I'm creating Joilet for an imagined MOBA, so three lane hero focused game play.
My initial reference was from victorian and school uniform influences, but I believe that's a little too narrow. Up next is a lot more iteration/exploration focused on clothing and facial characteristics!
Great concepts so far! Nice costume sketches too. I love the jacket and hair of the first one, and wonder how she'd look with the longer leggings of #2. The idea of varying her skin tone is interesting, but I don't know about making her a full-on puppet as in #3: It gets confusing if she's controlling the puppets and is a puppet! (Neat jacket, though - I love the parts that hang down past the skirt and the huge cuffs.)
Good luck whichever you choose, and have fun! 
Thanks! Yeah the puppet was in fact my first go, but I felt the same, a little redundant and confusing to have her be a puppet as well. >.<
I think you should go with 5, looks great!
Update! I'm continuing on with the painting process as I feel my concept sheet is in a fairly solid place now. My game plan is to work from grayscale to color using gradient maps and a few layer modes.
As of now I am also recording my painting sessions so that I may stitch them together in AfterEffects and show a full timelapse of this entire process!
Very Cool designs! I like the overall composition, but it looks a bit to well composed and symmetric, you might want to create some imbalance.
Thanks for bringing that up Grafik, this evening I spent a little more time making decisions on what the overall flow was and moving/removing elements.
On a side note has anyone had an issue with selecting value on a grayscale layer using 'Current Layer' mode when gradient maps are involved?
I dont know why but it select colors at random from the gradient map clipping the folder. This seems to happen on and off but can be a real pain when I want to see how my value is translating to color.
Hahaha Sasori much? 
Looks absolutely great!! Looking forward to see more 
Oh my god you're right. Glad I didn't make her a ninja...at least aesthetically different? ahah. Expect to see more soon!
Oh she looks great! Love the setting of the illustration, it shows great promise
Haha yeah it's completely different visually don't worry 
Just her Lore kinda reminded me of him. You know: Turning your enemies into puppets and stuff. But still I'm really digging your design!
@evehartman Thanks!! Yeah I was thinking an urban night scene would be a break from what I've done in the past. Here's to trying!
@Prophantii There is just something so cool about a villain who's whole shtick revolves around enslaving defeated enemies. I think it's a theme a lot of artists enjoy exploring, I just finished Stardust Crusaders and most villains in that show have a sadistic/manipulative nature to them and can enslave others.
Here is another on the ol' updates! I continued refining with value and messing with positioning. I plan to do the same treatment again, and add some more color. Right now I'm holding back on applying a great deal of color, the silhouettes for the hair and figures are not definite yet, and it can be a huge pain to go back and adjust masks/manage more layers if I start to soon.
I think I squeezed as much time out of this weekend as possible. I planned to post in the evening, but I wanted to get this update posted before I make more changes.
Painting continues to go well, started adding more love to the 'Slasher' doll at the forefront, adding detail to trees, and Joliet materials/hand as well. I also made the magical circle into a smart object so I can freely alter it without being destructive. Plan to look at some DOOM reference to hit home the demonic feel.
My personal stretch goal at the start of this contest was to record and upload my enitre process and I have done well so far. I'm up to Part 18 and a total of 3 Gigs of footage!
Once the contest is closed I will begin editing and upload to my youtube soon after!
This is coming out nicely. One thing I noticed is the character's left eye which is in shadow needs reflections
