My idea is this:
1. When simmies grows up, they generate outfits to fill up any slots. Until there are 3 outfits on each category.
2. When they get changed automatically, like going out, going to bed, etc., they will pick randomly from the existing 3 outfits instead of always changing into outfit 1 of the category.
3. Add an interaction of randomize outfit to the wordrobe so outfits can be random generated without going into CAS. Particularly, should call up the outfit chooser to choose which outfit slot to be randomized.

Things I have done so far:
1. Spent 5 hours of search for nothing.
2. Installed everything about modding: SimPE, SDK, Refrector, etc. I can find ildasm.exe but no ilasm yet.
3. I study C++ in University, however the code in those is nothing C++ but C#. (I thought they are the same but it turns out that my dev-cpp didn't recognise any class or method so I think they're different.)

Things I need:
1. A quick guide to C#.
2. Tips on which classes should I look into.
3. ilasm.exe
4. Loads of support from you guys.
5. Time.

Doing this will have a decidedly negative effect on both save file sizes and game lag.

Doing this will have a decidedly negative effect on game lag, as anytime a sim attempts to change into an outfit that is not cached, they will freeze in place, possibly for a very long time if your computer is crap, until that outfit is loaded. Because the outfits are chosen at random, the computer will be unable to predict in advance what to cache and performance will go straight down the tubes. Also, whatever outfit you choose apparently becomes outfit 0. It will also render most sims completely unidentifiable, as Generic Puddingface Syndrome quickly renders most other sims in the world indistinguishable except by their uniforms.

Can be done. The outcome will almost assuredly be horrendous.

I think you need to master the use of Google first.

That's one way of looking at it. The fact that you actually tried this and consider this important is probably not helping you at all. Here's a tip: I don't actually know anything about C#, and it won't help you anyway since you then get to do everything in MSIL.

Wing it. When in doubt, Google.

If I could tell you that, I could just do this entire hack for you instead.

http://www.lmgtfy.com/?q=ilasm

With the kind of thing you're doing, if we could give you any support with it, we could just do it ourselves faster.

Thanks for your reply mate.
So I think I will just try to do the mod to the dresser then.