I was wondering when Lizzi was going to post on this thread. :D

Hmmm........
Anime style? I suppose I could do something similar, Although I'm not sure I can promise it will be finished until the end of the week.
I will not charge for it, But I cannot reassure that it will fit your tastes or quality, Seeing as my forte is pencil and paper, I'll be going outside of my comfort zone.
I need a bit more description, How should I set the theme? Do you want a specific emotion displayed? Do you want a specific background?

This is going to take MUCH longer than I thought. 2-3 days, maybe. It's most likely due to my lack of favor of PC Art.

Here, After a good amount of procrastination and fury over perfectionism, The sketch has been finished.
Alright, I'll change that when I get to the drawing itself.
Think of it like concept art for a book, If that makes sense- I don't post the picture until I think it's good, even if it's a sketch. It's a 4/5 step process,
Sketch, Upload, Listen for how I could improve, Draw, Upload.

Bloop. Second try. I took all your suggestions for her body proportions. I did this without an internet connection so I didn't have access to any references xD

http://puu.sh/79Cyl.png

Tell me if there's still something you want to change.

EDIT: She's still too short, comparing to your original reference >.<

Tucked in? That's not how the Grey Owlite cloak is designed though

Egh. Really hard translating grey feather to a human form.

V3: http://puu.sh/79DUY.png

This... this could have been a really helpful ref to give in the first place. :/

Edit: Sigh. V4: http://puu.sh/79Fbn.png

Is this what you are looking for?

V5. http://puu.sh/79J66.png

V6. http://puu.sh/79JJe.png

Full drawing is scaling out at 4500x3000, yo.

My entry

I'm not good at doing eyes :/

He/she's so much better at art than me... But maybe I can try and do something? I dunno, I'm bored and I've got artist's block (is that even a thing?)

So instead of doing what I normally do with outlining and coloring, I've decided to take a more painterly route with this drawing. So it'll end up more like a lineless painting rather than a lined chibi.

For now, here's a WIP of the dark forest background. This will sorta define the mood of the whole piece, so tell me if you want me to make any changes.

Background by itself: http://puu.sh/7ftVv.png
Background with Gwen silhouette: http://puu.sh/7fuqy.png

I legit want to see all the pictures from this post photoshopped together.

There's a lot of different approaches...

You could layer thin strands of hair on top of one another using different sized brushes.

Using a combination of both thick and thin would work.

Making the hair a solid shape and then adding depth and texture would work.

And highlight is a must for hair.

For Gwen's image, I suggest allowing the hair strands to float and whip around, or at least make a sort of frame for her face without making straight bangs. Also, covering the eyebrows will remove any expression you gave her using the eyebrows, so try not to have too many bangs that go beneath the forehead or lower the face. Alternatively, you could add a few bangs that go in between the eyebrows.

You can use this as a sort of help for an anime-style approach :

http://www.deviantart.com/art/Spiral-Knights-Sketch-Vinnydime-366425266

In the method of the link, the eyebrows are re-drawn ABOVE the layer of bangs, making them still visible. Realistic eyebrows are not recommended for that approach, as strands of eyebrow will be lost or conflicting with strands of individual bangs or hair.

Subjectively (mark my words, I am nowhere near a good artist, but I just analyze a lot of things for compensation), I liked your rough draft version better. If you had increased contrast and removed all saturation of color, you'd have a very good black-and-white fill-in-the-blank sort of template to work with. It shows expressions more easily and anime-like than your current draft, and it doesn't look like it's trying too hard for a blend of realism with the anime-style Thin wanted.