Hello, sorry for the incredibly late reply.
I managed to get this working once, very delicately following what they did in this blog type of thing (and other blog posts that are now gone): Layered Clothing (roblox.com)
Proof:
(Example of the whole thing working)
(Example of the clothes layering on top of each other properly)
(I was DMing GolgiToad about it, also heres the timestamp, this was in April this year)
Unfortunately I was going through a major depressive episode at the time and literally forgot most of the stuff I did (I’m not even kidding, this is a thing that happens). I decided to try to remake this whole thing again and saw this thread as I was looking for guides, thinking that by now people would’ve discovered how to do this. But this is the only thread even remotely mentioning it. So here I am, reverse engineering what I’ve already done.
But first. Essentially, to answer your questions:
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You will need to create your layered clothing on the mannequin provided by Roblox. It has to fit that mannequin, and will later deform to your custom character. How so? Read on.
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To make it compatible, you will need to make your rig follow the r15 schema. This means segmenting your custom skinned character, and naming the segments like r15 bodyparts. The official blog post mentions some stuff about this.
This also means that your armature/rig itself will need to be r15 compatible. This means one bone for every body segment, plus two bones called Root and HumanoidRootBone that share positions with the world origin. Also, did I mention, you will need to put your character’s waist on the world origin.
Should look something like this:
Also, you will need to scale your character down to like 0.001% of its size (for proper measurements import the default mannequin). Its super inconvenient to edit your character like this, so I recommend you always just do it before exporting and then revert it to normal. This is because the conversion between the Roblox engine and other standard 3d modeling software is super weird for no reason.
If you don’t do this then the clothing you wear will be super small instead, here’s a video of when I encountered this:
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And here comes the important part:
Take the outercage from the mannequin and import it into your file with your custom character. Yeah. You have to use the same outercage for your character as that realistic mannequin. Its gonna be ugly, but the way to make it fit is with the shrinkwrap modifier. And when I say ugly, I mean it, this is how it looked on my character. (Granted, I was pretty lazy with it and just wanted to get it working asap)
Try to edit it with proportional edit and symmetry mode on.
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Also don’t forget: Put these little orbs on specific parts of your mesh. These will help with attaching attachments and the layered clothing itself. The mannequin used to have a lot more of them but the newer version only seems to have 7, in any case here’s how my rig had them placed:
The now deleted blog post also had some advice on how to place it, you basically gotta make it slightly go into your character’s mesh. Not floating away from it, not just touching it, but like a good 40% of the orb should be inside your mesh.
As I’ve mentioned, there was a really handy article that had a lot of resources for importing custom r15 rigs but Roblox decided to “update” the page and now it contains pretty much only surface level information.
(the link I sent to GolgiToad, while discussing this)
External Modeling | Roblox Creator Documentation (where the link redirects you now, as you can see it contains nothing related to custom characters)
But we are in luck, as the mannequin still has the proper rig. In fact it is probably the biggest help in this reverse engineering process, so go grab the newest release!
As I’ve mentioned, this new mannequin only seems to have a few of the attachment orbs. I’m quite sure this is because these are the attachments necessary for layered clothing to work, but idk if the other orbs they’ve deleted are obsolete now or your rig should still have them. In either case, I’m pretty sure you can download older versions from github, so go back to whichever release was available in April, because that’s the one I used and the one that had all the orbs I’m talking about.
Anyhow, that is all I recall. I’m gonna attempt to redo this and if I find something I was wrong about, I’ll edit this post. Feel free to ask me about anything. If there’s demand for it I can make a video guide as well.