OK, knowing there was a picture of Eve out there, somewhere, I did a search and found it. She’s brunette! She’s beautiful! And by safer, hon – I mean on your follicles. Heaven forbid I advise you to play it safe. 
My shorn locks are brunette, BTW; I’ve never considered not being blonde a handicap.
How can my red hair be a lie if I no longer remember the natural color of my hair? 
-Merlot-
Dr. Eve, report to exam room #4, please.
I am rapidly aproaching 50% gray but I do not use permanent color. I still continue to use semi-permanent. If you were buying over the counter then that would be Clairol’s Natural Instincts (my fav), Lasting Color or Loreal’s Casting. These colors have no ammonia and less peroxide. They wash out gradually in, they say, 24 shampoos. It usually lasts me 6 weeks or so.
Semi-permanent does not lighten hair. And you still have to be careful if you dye your own hair. I’ve done countless corrective colors on people who dye their own hair. Usually, what happens is they don’t know the laws of haircoloring and they put on whatever and don’t get the results they want. I’ve had to bleach out hair that got too dark, people that tried to go blonde and ended up with blue, green, or strange shades of brassiness. So I’ll repeat my mantra: “Ask your hairstylist”. He/she will know what will work best and how to do it.
When I make a brunette blonde and she doesn’t want to keep coming back to do the roots, I usually recommend highlights because the roots aren’t so obvious. or I’ll do a solid color and the follow-ups as a highlight. Since you come up red, you’ll have to see what system of color your stylist uses to correct that and go from there.
Oh, and I say go for it! Don’t get your heart set on a certain shade. Go with what works best on you. If you don’t like it you can dye it back, but that does take multiple visits. So no matter what you decide have your wallet ready! 
Eve, go for it. The world needs more filthy looking blondes.
I am horrificly pale and completely bleached my hair a few years ago and LOVED it. So, I say go for it!
And if it doesn’t work out quite as filthy as you’d hoped, you know not to do it again as opposed to wondering what it would have been like if you hadn’t.
You know, I’ve been reading that book (turns out I had read chunks of it before I knew the author, but I have a new perspective and happy to suck up whenever possible) and I really like the author’s look. New England patrician with vaguely Jewish overtones. Killer look. You might want to go for something like that, only a bit more mature.
First, that 1991 makeup HAS to go. Those cheekbones can stand on their own. As can that long, stately nose. And the hair put up, but with strands escaping, gives that Gibson Girl effect already mentioned. The hair could be darker to give the now-natural skin tones a chance.
Get that retouch artist back in here–time for a makeover!
Sufficient sucking up, oh Mistress of the Past?
What Jayron 32 said. And this from a guy who, all other things being equal, does (slightly) prefer blondes.
Setting aside considerations of practicality (this is an aesthetic dilemma and I will not have it polluted by such pedestrian subjects as “maintenance,” or “chemical burns”), I cannot but regard any quest for a higher filthiness quotient as anything short of Holy. Also, as has become apparent, I cannot, as a rule, employ a short, concise sentence when a cumbersome, convoluted one may be used in its stead. But I digress.
Perhaps I’m a regional chauvinist, but I give the big thumbs-up to the “Connecticut blonde” idea. It’s quite an attractive hair color, and lends itself well to being worn up (although, to be honest, nothing beats brunette for upswept hair).
And your motives are unimpeachable. You can never be too rich or too filthy, 'far as I’m concerned. While like the rest of the guys my own preference leans toward women who look more natural than not, the color you’re going for is fairly subdued, and–most importantly–we’re not talking about me here. In sum: Go on with your bad self.
I say go for it. I’m sure if you go to a competent colorist, they will give you a hair color that suits you. It’s quite a change doing something new with your hair (and a bit nerve wracking, i admit). I had mine cut very short recently and also lightened the top up so it was a few shades lighter than it is. I was nervous about getting it done so short, but I got good remarks from family and friends, and everyone says I look more adult now. As for the lightening, when I style my hair, the gel makes the hair look darker, and the lightened part fades into the untouched rest of my hair. It’s not really that noticeable unless i’m in the sun where it really shows (if i’m in the sun a lot, i’ll often find red, and even blondish hairs).
Then again, i’m a college student, and we do odd stuff with our hair. I considered dying it blue before my family and I went down to Costa Mesa in So Cal for the family reunion, but decided I didn’t want to shock my moms’ relatives that much.
What the heck. This thread deserves a 50th post.
He’s right about the world needing more filthy blondes.
Regarding another current thread – report to examining room #2 Brat’s busy so I’ll handle this one myself.
SouthernStyle
Well, I decided to make a consultation app’t. with a good colorist I’ll get someone in the fashion dept. at work to recommend.
Said colorist will probably talk me out of it (“a double process on long hair—are you MAD?”); I’ll let you know! Thanks for the input . . .
If you’ll consider a coloring fascist with a good consultant I’m available. And affordable.
SouthernStyle
I have decided that since I have no idea what you look like, I have no valid input as to whether the flithy blonde look would be good on ya.
Sadly, this necessitates the withdrawal of my earlier remarks. 