Also, as for the attempted jab at consumerism that you commented about, I'd like to clarify that it wasn't meant as a jab at all. I didn't even mean for this VN to be anti-clothing at all. In fact, I was a little worried that I was being a little too pro-clothing since every time Cliff brings up a good reason for wearing clothes, all Devon answers with is "Well, that's stupid." So it wasn't meant to be commentary on consumerism or anything, it's simply not what Cliff want out of life and it's Cliff realizing what he does want, which is just someone who's willing to listen to him. I usually try to write stories with more complexity, but due to the constraints of this jam, I really couldn't convey a message more complex than "It's good to be around people who understand you!" but that's the way the story went.
Thanks for the detailed response! It's always nice to have additional insight into the design process whether things worked or not.
As you say, I think some of these things could have been conveyed a bit more cleanly. I certainly didn't get the feeling that we were pre-20th century in the setting; the architecture, fashion (including the backpack, which looks very modern Edit: disregard - I re-downloaded to double check and it's less modern than I remembered), speaking mannerisms, etc. didn't give any indication that this was supposed to take place significantly outside of current times. As for the state of clothing dump, if you were trying to create an image of a ruined town, there are fairly simple details you could add to do that, like having Cliff trip over a pile of rubble, or noticing non-clothing debris jutting out from the clothing and wondering why it's there.
Ultimately, I feel like the worldbuilding is set up to support individual scenes rather than the scenes taking place in a cohesively built world. I feel like you wanted it to be longer than 20 years of degradation, but couldn't do that because Cliff needed to be alive when the disease started and needed to be in his 20s or 30s to be an eligible VN bachelor. I feel like the reason we don't see ruins or debris is to set up the sudden reveal with Cliff not realizing he was hiding behind a chimney. The reason the vestipository isn't set up like a normal landfill with multiple layers filling a hole in the ground is because Cliff needs to tiptoe between the piles on solid ground, and so on. I think there are ways you could've combined these details to make the scene flow more smoothly. Instead of having Cliff tiptoe between the clothing, have him climb on rubble piles to avoid contact that way you set up the reveal that Cliff was using the remains of a former town. (and yes, that may be morbid in a way. I also live in SoCal. But if you're going to include that plot point you might as well use it.) I'm not saying you didn't consider any of these things when writing the story, but rather just how the details came across as a reader.
Regarding the other points you made, I wouldn't say the story comes across as anti-clothing so much as pro-nudity, but certainly not pro-clothing. Regardless of how unconvincing Devon's arguments were, that's still the conclusion that Cliff also reaches, and the line about latest fashions did come across as bitter. Kinda got at this towards the end of my original comment as well, but I'm not sure the message lands as intended either since the "understanding" is so superficial.