Trickster Mode seems (kinda obviously, given its origin) to have a connection to the cherubs and their folklore. Instead of their associated color being seen on the symbol on their clothing it is noticeable on their bulging eyes and spirals on their cheeks like those on cherubs.
In both cases, Trickster Mode has become associated with certain alterations in the physical appearance of human characters: their entire color scheme is altered to give them brightly-colored hair and clothes, some sort of object (usually a candy, dessert, or fruit item) is stuck in their hair, and their color-devoid aracial skin tone is changed to Caucasian a peachy color. Characters in Trickster Mode become disturbingly cheerful and have access to powers that alter reality in a surreal manner. In canon, it refers to a powerup acquired by licking the spiral sucker juju created by the fusion of Calliope and Caliborn's individual jujus.Several assets are swapped in Trickster Mode, such as swapping John Egbert for something generally foolish, and hidden locations can sometimes be accessed. Out of canon, it refers to an Easter egg available during a few of the interactive Flash animations that were programmed by Alexis 'Gankra' Beingessner.The name Trickster Mode is shared by two different but related concepts that involve the narrative of Homestuck being altered in silly and unpredictable ways.
Fanart of Roxy's Trickster Mode by Calliope.