(Click on the pictures for a larger version.)
 
Volume 16: Leo VOLUME 16: Leo (Special Edition Cover)

Leo sits on the floor reading a book, but glancing up just enough for us to see the golden Abyss lights dancing in his eyes. A very light-hearted cover for such a tragic character.

He is wearing the white and black uniform of the Lutwidge Academy. It's very tidy except for his bow, which is uneven and skewed to the side, maybe indicating that there's something not quite right about this boy.

Leo's color scheme is... rainbow. o.o;; Yes, Leo supports the LGBT community!

The five-pointed flower confetti parallel the carefree symbolism of five-pointed stars, since both appear around Leo whenever he's having fun and engaging in escapism - as he is here. Some of them are blending into his clothes. But these could also be a reference to the Abyss lights that Leo sees with his special "Glen" vision.

You may also notice that he has no chains at all! O.O;; Well, this can have a more mundane explanation. The scene is from before he contracted with Jabberwocky, and so he was Chain-free. This would reinforce the idea that those who appear with chains tied to them on their cover are Contractors.
Volume 17: Oz, Alice, Gil VOLUME 17: Alice, Oz, Gilbert (Special Edition Cover)

The upside-down-ness of this image jumps out at you right away. This is the point where everybody switched roles and nobody is who they thought they were.

Gilbert, who has dedicated his life to Oz, later rationalizing it by believing this was a way for him to atone for failing to protect Jack 100 years ago, is hit with the realization that his real master was Glen. That he himself is a Baskerville, that it is Glen who he had failed to protect from Jack, and that he had spent his new life helping his beloved Master's enemies.

Black Alice actually opposed Jack 100 years ago, and we discover that she is not the Black Rabbit. Oz is. And so he wears a rabbit pendant pinned to his tie. But more interesting are the clocks he wears. One is an hourglass hanging off a string of gold pearls (both gold and pearls being Abyss symbols). The other is a black watch with gold roman numerals that's half-covered by his shirt.

In the pilot chapter, the Black Rabbit chain (referred to as an "abyss") is said to control time. The clock at the Vessalius mansion stood silent for 100 years, associated with a prophecy that said: "when the one whom we await descends upon the promised land, the bell will toll to break the silence." By touching the clock, Oz was able to start it up again. But what stopped it in the first place?

In recreating the Tragedy of Sablier, Yura included a replica of this clock at his party. Oz (Jack) was supposed to rescue Alice from being sacrificed before midnight. The Vessalius clock was frozen at midnight, too. Perhaps whatever stopped the clock of prophecy 100 years ago was related to the Tragedy of Sablier, and to the probable time powers of the Black Rabbit (Oz) chain that Jack wielded.

Some of the pearls in this picture are gold, representing the harmonious Abyss; some are black, representing the darkness which later engulfed it. Despite Gil being set against Oz now, they are still bound by a gold ribbon at their left, passive, subconscious arm. Their bond is strong.
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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!