I realized, eventually, that the girl being described by Mr. Cakey is almost the exact opposite of my ideal significant other. I try to avoid forming an exact image of my "ideal girl", of course, because that kind of thing can prevent you from really seeing people, but I do have a general idea.

I want a girl with a mind like a diamond
Diamonds are hard, pointy, and completely lacking in colour. They are beautiful, it's true, but only really have value because of societal convention. To a man stranded in a desert, diamonds are the height of uselessness.

I want a girl who knows what's best
"Knowing what's best" is the sort of phrase authourity figures use on small children. Listen to the adults, they know what's best. Now, please understand, I have no real problem with that in an actual hierarchical relationship. I'm perfectly capable of following orders. Ideally, however, romantic partners should be equals. I can't imagine living with someone who actually knew what was best, much less did it. I prefer her to be as surprised as me.

I want a girl with shoes that cut
To what does this refer? Stillettos? Skates? Either way, it sounds hard, professional, and uncomfortable. I've always hated the stereotype of women who buy too many shoes. What's the point? I own a pair of winter boots, a pair of sandals, a pair of running shoes and a pair of dress shoes. That's all I need. In fact, I probably don't even need that.
I want a girl with sandals that make a "scouge" sound in damp beach sand.

And eyes that burn like cigarettes
This one is the worst. Cigarettes have not been cool since James Dean. They are filthy, addictive and deadly, and everyone knows it. I can't, for the life of me, figure out how people even start smoking. Who on earth is providing the peer pressure?
Eyes, as the window to the soul, should be bright, clear, and have a well-defined eyebrow. Red, smouldering eyes are for incubi.

I want a girl with the right allocations
I don't even know what this one is supposed to mean, but "allocations" is an accounting word. That's a turn-off, right there. It suggests quantification, which is a phenomenally bad thing in one's personal relationships. I don't need to see a resumé and the phone numbers of three previous employers.

Who is fast and thorough and sharp as a tack
Pretty hard to argue with this one. Fast, thorough and sharp-- those are all pretty much good things. I suppose it is possible to be too fast or too thorough, depending on context.

She's playing with her jewelry
Jewelry. Ick.
Never much cared for jewelry. My Mom likes to complain about the outlandish piercings of others, and I, in return, like to remind her of the gaping holes that were punched in both of her earlobes. I don't wear jewelry, unless you count my wristwatch. It's made of plastic.
Playing with one's jewelry... that's probably the first indication that the object of this song is actually human. Fidgeting is a very biological action, indicating that whatever leftover pieces of brain aren't being used in the task at hand are getting restless. I like to watch people fidget, especially if they subconsciously do it to a rhythm.

She's putting up her hair
Another ick.
This lyric puts an image in my mind of old elementary school teachers with eighteen inch wooden rulers. Most notably, that of Mrs. Plewes, who taught me in first and second grade. Wonderful woman, to be honest. Salt of the earth. I didn't really find her attractive, though, possibly because she was a good half-century my senior. She used to say things like "hustle your bustle".
I believe she may actually have worn a bustle at some point.

She's touring the facility and picking up slack
Euugh. Efficiency.
"Efficiency" means getting fewer people to do more for less. It does wonders for the bottom line and keeps the stockholders happy, but makes everyone else miserable.
Do not tour the facilities.
They're fine.
She governs best who governs least.

I want a girl with a short skirt and a long jacket
And thus, we come to the title and theme of the song. To be honest, I think this bit was selected for its sound, rather than its meaning. Short skirt and a loooooooooooooong jacket. Long jackets are nice, I guess. Trench coats, even. Very sexy. I remember the day after the Columbine shootings, I accidentally wore a black trench coat to school. It wasn't my fault. I was doing a dramatic presentation in French, and I was playing a private eye. I just never put two and two together.
Even the goths were wearing white.
I was a little unnerved at the reaction I got, but I never took it off.

I want a girl who gets up early
I am not a morning person.
I can function, alright, but I don't like it. No, let me sleep in whenever possible.

I want a girl who stays up late
I am somewhat of an insomniac, which may contribute to the prior point. I really don't know how to fall asleep.
I remember reading about a study done where they sealed people in rooms with no indications of the time. Most of them gradually developed a twenty-four hourish sleep pattern. A minority, however, went over to a thirty-two hour cycle, and were dazed, disconcerted and confused when the study was over. I strongly suspect I may be a thirty-two hour person.

I want a girl with uninterrupted prosperity
I have a gut reaction to this line, and that gut reaction is "Bah, how horribly shallow.".
That's probably not being fair to the singer, though. I mean, he's not after her money, is he? I don't think he's after her money.

Who uses a machete to cut through red tape
We all hate red tape, I suppose. Wating in lines, filling out forms, all that impersonal formality when five minutes with a real human being would convey all the necessary information with time left over for a bathroom break. No one likes waiting.
I don't, however, especially hate waiting. I can appreciate the time spent in line. I imagine I annoy others, because I hum to myself and pick at things. It takes a very long time in a situation like that for me to get bored.
My Mom always says that smart people are never bored. I guess, in some cases, she's correct.

With fingernails that shine like justice
Fingernail polish falls under the same category as jewelry, I guess. Shining like justice-- that's certainly an odd way of putting it. It wouldn't quite be the same if her jewelry shone like justice and she played with her cuticles.
I suppose justice shines, but in a very definite kind of way. The same kind of beauty as a diamond-- polished and inorganic. Very nice, if she's your business partner. Not so nice if she's your girlfriend.
I'm noticing that sort of theme here. Perhaps the song is actually about the kind of girl he'd like to hire.

And a voice that is dark like tinted glass
A nice, silky voice is always a plus. I, personally, pride myself on my ability to speak.
I don't particularly enjoy speaking in public, but I've been told that I'm good at it. I once had to give a speech (of sorts) in eighth grade, and I decided to go five minutes on the subject of Solanum Tuberosum, our friend the common potato. To this day I'm known by my contemporaries as "the potato man".
It's quite disconcerting, especially when I'm greeted as such by someone I don't recognize.
Tinted glass, though... is a voice like tinted glass a good thing?

She is fast, thorough and sharp as a tack
She is touring the facility and picking up slack
I want a girl with a short skirt and a long long jacket
...and we're back.

I want a girl with a smooth liquidation
Another head-scratcher. Fluidity of motion is always attractive, I suppose. Given the financial undertones of the other lines, though, it could refer to some company liquidating its goods. Massive savings! Everything must go!
In which case, of course, "a girl with a smooth liquidation" is one who is skilled in selling out.

I want a girl with good dividends
By this point, I'm actually starting to hope that this is a euphemism for large mammary glands. It isn't, though. It means a girl with lots of money.
Possibly, enough money to purchase large mammary glands.

At Citibank we will meet accidentally
Of course they meet at Citibank. Where else? They get to comparing their mutual fund portfolios, and it just blossoms into romance from there.I never know where to go in order to meet people. I just go places, and people happen to be there, and I meet them.
Maybe that's my problem. I need to hang around banks more often.

We'll start to talk when she borrows my pen
I hate how conversations require a catalyst like that. I wish I could just walk up to people and start talking, like in an RPG. I want to strike up philosophical discussions with the people I see on the bus.
But I don't. No one wants to talk to a stranger, especially not one using public transit.

She wants a car with a cupholder armrest
Practical, I guess. She likes to drive and drink coffee, or possiby some sort of soft drink.
I like cupholders myself, but it's not the main thing I look for when purchasing an automobile. If I find a really cool car at a really great price, I can make a cupholder.

She wants a car that will get her there
As opposed to one of those newfangled "stationary" cars?

She's changing her name from Kitty to Karen
I'm not crazy about either, to tell the truth. I like names that begin with vowels, for some reason. They just sound feminine.

She's trading her MG for a white Chrysler LeBaron
I had to actually see pictures of these cars before this bit made sense. The LeBaron is a more sensible, adult vehicle. It ties in with the name change-- a switch over to maturity. That just seems wrong to me.
You shouldn't have to make deliberate changes in order to ascend into maturity. Those changes should come naturally, without you realizing it. I consider myself to be a fairly mature person, my status as a cartoonist notwithstanding.

I want a girl with a short skirt and a long jacket
And we come back to the title. The singer has found a glamorous rich girl, domesticated her, and will now undoubtedly enjoy years of marital bliss until the pressure becomes too much for her, and she leaves him for Carlos the pool boy.

If you really feel like it, you can see my brother's video here.

Just don't listen to the lyrics.