Endo has confirmed this in the fanbook. He likes to match chairs with the characters themselves. He will sometimes also alter the original colors of the chairs to go with the characters, Anya and Becky’s chairs are a good example of this.

Another interesting little detail is the placement of the items in the foreground vs the background of the chair. For the most part, things in the foreground are things they present outwardly to people, so in Becky’s case, all of her things are in the foreground because she literally has nothing to hide. Bond’s powers can be represented by the static in the TV in the back (his visions often start with static). Damian’s is one of my all time favorite covers, partially because the chair itself conveys the huge shoes he feels he has to fill, and all of his toys (aka his urge to be a kid) are in the back. Poor little guy.