Do you have any specific resources or tips on how this relates to clothing? I've done this, and tried to argue my case in color choices based on this, but generally I've been laughed at when I bring this up. (probably because other factors also come into play and I'm about as blind as a mole when it comes to choosing colors).
We're talking about art here more than science, so there's no breakthrough right answer like in mathematics. My experience is that I'm more savvy and I start to notice the patterns, but my skill level isn't high enough that I can lecture on the topic intelligently. It's like, after doing all this stuff I have intuitions when shopping for clothing and dressing, and I tend to get complimented on what I wear, which didn't happen before I studied.
I hate vague answers like that - I wish I could give you something more concrete. It's not the "oh you just have to figure it out" whimsical idealism, it's that I lack the skill to give a more cohesive and concrete explanation... apologies for that. If you know anyone who is an excellent photographer or painter, and is also good at explaining things analytical, they might be able to provide more answers.
One tenet of color theory.
Smashing Magazine (which doubles as good for web design).
Study the color wheel, read analyses of ways to use it.
Fashion websites.
Go to lots of museums.
Go to art galleries.
Flip through 2-3 fashion magazines per month at the bookstore.
Read book(s) on how to dress for different functions.
Go to high end stores and try things on.
Talk to artists, designers, architects, painters, etc. about why things look the way they look.
Take some art class, either crafting/doing-based, or art history.
Go with some sort of visual artist to a museum, and ask their thoughts about paintings.
Get a girlfriend/boyfriend/significant other who is an artist.
Any of those would help. The more you layer on, probably the faster you learn.
Also, study fashion/clothing advertisements. Scrutinize and analyze why they chose what they chose... many fashion ads will be regarded as high art in the distant future, because immense amounts of preparation, lighting, setting, and skill goes into making them. Almost anything that's in one is in it for a reason. Look at it and ask, "Why did they choose this? What are they trying to say/portray? Why this background/environment with that sort of clothing?" It's not instant gratification on the last one, but soon you start seeing the patterns. It's kind of beautifully awesome when you do.