Watch For: flowers, roses, mysterious hands, ribbons, pearls, chains, cages, feathers, wings, butterflies, skulls, crowns, crosses, chessboards, curtains, stars, rabbits, mirrors, earrings, colors.

If you still have any doubt about the prevalence of meaningful symbolism in Jun's artwork, I give you: Gilbert, with a tiny feather in a tiny cage and a tiny key:
Gilbert with a Feather, Cage, and Key
Alice with Caged B-Rabbit

A tiny key and a feather in a cage are simply too random for Gilbert to be holding for no reason, so they gotta mean something!

Perhaps this is the blue feather representing Gil's love and devotion that he never got the chance to give Oz during St. Belligeron's Day, chained as it is to Oz, and showing how possessive Gil is(/was? XD) of Oz. The little key is small enough to open this cage, and perhaps echoes Break's words to Gil - "a loyalty that holds fast will become a blade, and will someday pierce those you hold dear" - warning him not to grasp onto Oz so tightly.

But Raven's black feathers are all over this picture. Maybe it's more likely that this feather in a cage is symbolic of Gil's contract with Raven, further reinforced by it dangling on a chain. After all, his contract is anchored onto an amulet that he carries around on a chain. They key in this context would represent Raven granting access to the Abyss.

The concept of keeping Chains in cages is connected to the wish-granting aspect of the color blue, as with blue roses. And, actually, all the cages I've seen are linked to blue roses.

On the left is dark Alice holding B-Rabbit in a cage garlanded with blue roses (and some unknown pink flower). It again suggests the Black Rabbit power is separate from her.
Ada with a Caged Skull

Ada has been seen with yellow roses, which are common to the Vessalius dukedom, as well as blue roses and black roses. In the picture above she has all three.

She has a torture device on her left, probably from her occult dungeon, and the seat cushion behind her is ripped. On her right side is a caged skull. The blue rose wrapping around the skull's cage is wilting. Well, either that or she sprinkled extra blue petals around. Tied as Ada is to the sorcery, the symbols around her might be particularly important.

In the picture on the right Vincent has Ada in a cage instead. Her eyes and arms are bound by black ribbon, her wrists are shackled with chains, and black rose thorns grow all around them. The cage itself, though, has blue roses blooming on it.

The background is a pink and black chessboard, indicating a duality. Considering that Ada is wearing pink and Vincent is wearing black, this makes sense. The strategic game being played on this chessboard is emphasized by a spider web, similar to the one in the picture of Alice with the skulls.

On Ada's side is the white pawn chess piece, showing her role in the game, and on Vincent's side is the white knight chess piece, showing what he looks like to Ada while her eyes are blind to his true intentions. In the bottom right is the Queen chess piece, foreshadowing Vincent's Queen of Hearts Chain.
Vincent with Caged Ada
Break in Gilbert's Cage

A cage features prominently in human Alice's room in Sablier, where she was kept in a tower by Glen. The overall sense of imprisonment is felt even in the bars on her windows and the wire fence-like pattern on her clock.

Cages, like chains, are symbols of bondage and entrapment. Such as the entrapment of a Chain by a Contractor... or the other way around? But they could also mean protection.

Continuing the theme of people in cages, recall the picture of Break with the white rose again (I'm sorry for putting you in the "Stuff in Cages" category, sweetie ^_^;;).

I've always thought that Gilbert's presence here was just to show him releasing Raven, since those are Raven's wings next to him. But, if you look closely, Break looks like he's inside a cage.

Gil does tend to put things important to him in "cages." The picture is from chapter 55, when Break was fighting a losing battle against two Baskervilles and was forced to take a suicidal gamble and release Mad Hatter.

Raven realized that Break's life-force (white rose) was weakening, so he came over there to interrupt the fight and help. In doing so, he did manage to restrain Break's Mad Hatter power and stood as a physical barrier between Break and the Baskervilles, shielding him inside a metaphorical cage... and allowing the dis-empowerment of Break's handicap to sink in.
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DISCLAIMER: Pandora Hearts and all the characters, story, and art therein is copyright Jun Mochizuki. No copyright infringement is intended, and I hope that this essay inspires more people to read/watch Pandora Hearts! Translations are by Yen Press and Fallen Syndicate. Visit the Thanks page to see who else helped!