The final list as we know it, but do not understand it.

On your guess, Jeremy, Curt said that Tim as mitten was correct. He also said that your anime guess was half right. Therefore, we have deduced that:

Wise men: Amy
Santa Teddy: Jeremy
Mittens: Tim
Skis: Krissy
Ornament: Ashley
Anime: Krisemy

Reindeer: Angela
Peppermint: Ben
Candle: Tamy
Nativity: Bashley

To our knowledge, this list is accurate. However, we are still completely lost as to the why.

Spelling within the picture titles and other completely random guesses are all we have.

Crazy.

We must know the why.

We are all tired and must sleep now. Hopefully the correct answer will come in a dream.

Good night and good luck.