Sly Nye (1996), Factol Rhys (1994), and an unnamed aasimar (1996), all by Tony DiTerlizzi.
God deterlizzi's art fucks. Burned into how I imagine the dnd aesthetic
One of my favorite visual details from the Planescape art run are background characters whose costumes are overtly bug-coded, when there is zero textual mention of this aesthetic choice. AD&D Planescape is full of character designs that (a) seem to be clothes-shopping from the same store and (b) are shopping from a store no other setting is shopping from.
On the one hand, these recurring aesthetic flourishes (heavy use of ornamental spikes and blades, billowing pantaloons, mix-and-match piecemeal armor and casualwear, bug motifs) are hugely important to Planescape having a cohesive cultural aesthetic. Sigil needs to feel like a distinct place, a melting pot whose alloy of cultures is something new, with a culture that one can recognize in its own right. It must feel alien, and not a transplant of an existing Earthly culture. On the other, a lot of these motifs help to anchor the setting in the late Renaissance and early industrial revolution, rather than in the late medieval period. Consider: pretty much every costume in Gangs of New York (2002) would fit right into Sigil's crowds, and some of the truly questionable headwear (like our stag beetle friend above) harkens back to the fashion excesses of 18th century nobility without being explicitly coded as such. It almost feels like someone was running around shouting "no wigs!" Edna-Mode-style while figuring out other silly headgear to put on People Of Import. So Planescape not only feels like a different place, it feels like it's a different era, which far better serves its themes.
Contrast this with the "Wizards Of The Coast House Style" that migrated from M:tG to D&D after TSR was acquired, in which the clothes somehow make less sense and yet don't seem to be from anywhere/anywhen or for anyone. That's no slight against the hundreds of artists who have produced work for WotC; rather, I think it's a symptom of having hundreds of talented artists, working piecemeal, sort of stuck orbiting around the same bland average. Make a piece that strays too far from the average, and you're not getting invited back. Planescape feels as alive and fully realized as it does, I think, because of the fairly small nucleus of artists who established the setting's aesthetic in those critical first few products. DiTerlizzi, rk post, Dana Knutson, Robh Ruppel, Rob Lazzaretti: even if you're not wild about their art, it's impossible to understate their contribution to Planescape as a grimy, discomforting, cohesive whole.
