Coord Challenge & When Does It Stop Being Lolita?

[shampgn.livejournal.com]

Whilst shopping for the typical lolita-things that make a wardrobe full, I've bought some crazy accessories and dresses that I intended to use to make some "unique" lolita coords, but I'd like some opinions. I've searched near and far, but I'm not quite sure yet if I've found the right items to complete each look to make it work. 

Also, this is my first post. Yikes. Nervous! By the way, the main question is at the end. 

I do have typical wonderful lolita clothing items, and I'm not a complete nutso! I think...

I realize that, as far as posts go, this is edging on off-topic, however I shall still move on!

1. Cherry on top? - Easiest

  

The cherry headband has two dark cherries on a black headband with white polka dots. The shoes are very, very tall, white, almost knee-high boots, with pink ice cream, chocolate drizzle, whipped cream, and cherries as shown. I'd love to find a JSK/OP/skirt that would tie these two pieces together without making me look like an idiot. 

Would I:
1) Have a pink dress with a red/pink print on it, like Angelic Pretty's Strawberry Parlor in pink?
2) Have a black dress with a red/pink/white print on it, like above except in the black? >.> 
3) Red dress with white. Tie in pink in necklace form. (BTSSB cherry jsk perhaps?) 
4) Other?

2. 



I really regret missing BTSSB's Little Red Riding Hood. :( I feel like that would've matched this well, but that chance is missed and I've got a deer to deal with. Any ideas? Specific dress names would be fabulous. 

Should I:
1) Match it with a simple fabric dress of white/green/red. Keep it simple. Do any other simple taking of color. 
2) Garden glory? Picnic wonder? Mossy madness? Could I use some Dolly Kei inspiration? Any ideas? 

Deer god, help me! 

3. Main reason for post right here: Are these following too odd for lolita dresses?  

Can a dress maintain the general shape of the fashion and yet be "unfit" for its colors? Its print? Its material? Where do the lines blend? When is it out of the boundaries of lolita fashion? 

What would you pair with these? 

(Reminds me of Juliette et Justine vvv) 

(white part isn't part of dress; it's the mannequin)

I love this butterfly dress so much for some odd, odd reason. 

 
Could I make these lolita? It doesn't matter that much, but I don't want to be traveling to a totally different planet here. I suppose it is a different planet, especially if I'm only used to deco/sweet lolita. 

Well, that's that. I doubt many will read this post, but, to the few that do, thank you for any input. These dresses/accessories are stepping into territories I'm not quite familiar with. If it ain't lolita - call it. I guess this was just me being curious to how "out there" the fashion can get. As if lolita fashion wasn't already alternative, eh? 

Edit: I'm making some shoddy pics of some of the suggested outfits.

The first one I chose was taking from bat-shaped's comment. 
My vote is still out on this one. 
 Using the Red Riding Hood JSK...