For the past year or two, I've had the very strong impression that if I can figure out how to put tailoring into a computer game, I will have solved a major content generation problem.
If you look at games that allow player to generate clothing, you find there are two basic approaches.
The basic approach is to let players spray paint their avatars with a semitransparent image that looks vaguely like clothes. SecondLife actually offers a wide variety of twiddles and tweaks that allow you to do this in-game, but the result is pathologically ugly, so most of this kind of thing is made by importing an image from another program.
Reskinning like this is just not what I would consider a solution. It's begging the question. Clothing has a distinct existence from the avatar - or, at least, it should.
The other method is when you build clothes as a physical object and then somehow mount them on the avatar. While this produces clothes that have a distinct physicality, it runs into a wide variety of problems with varying body sizes and animations. Flowing clothes are essentially an impossibility, and forget clothes that interact with things (no stuffing your pants into your boots!).
Physical objects are subject to the rules of physical objects, and in modern engines that usually means solid-object physics and pre-scripted animations. Engines just aren't built for soft things. I guess a game that revolves entirely around the physics of soft things might be interesting, actually.
But a larger problem than physics is actually specifying the construction of the clothing.
If you're just reskinning, you don't have to worry about it: the construction is only skin deep, literally. Just paint whatever you like.
If you're building an actual object, the construction is usually very difficult, only made easier because the physics simulation is nonexistent so you don't have to worry about anything actually working. Most construction kits are built for solid objects like furniture, simple houses, and swords. Complex, adaptive physical constructs such as clothes and jet skis are usually quite difficult and certainly not mechanically interactive.
Many games - such as Project Entropia - solve this by having specific, tweakable blueprints. But that's not what I want. This problem is the heart of the issue, and is what I'm trying to solve. How would you (A) let the player create clothing designs and (B) simulate them on various avatars?
Remember, since we're working in a 3D space and can ignore gravity and the need to manually cut things, there's probably no reason to use 2D representations at any point.
This is not an easy problem: think about it.