Going from blonde to dark, how do I prevent it from looking unnatural, but still make it eye-catching?

So…just how startling do you want to be??? ;-O

Haha, @JilltheTooth right, that is what I’m trying to avoid. I would like an overall result similar to this, but not necessarily that color.

Yeah, I’d look like Liv Tyler with hair that color…:-P

Haha, well coming out if looking like Liv would be awesome, but I’m not delusional. I just think that she is a good example of fair skin and dark hair that doesn’t look like she just stepped out of a cemetery. Her cheeks always seem to be flushed, too, which is also true for me. So I think that helps to counteract the Halloween look.
Are you trying to talk me out of it? lol

The dark dark brows and lashes add to the effect. You don’t want to wash out your face…

@JilltheTooth definitely. Though, I don’t go anywhere without mascara. My brows are brown, but not nearly as dark as Liv’s. My hair is pretty dark in that photo, which I think was last year-ish, but I would like to go darker than that this time around.

Get it weaved. It’s more expensive than from a bottle, but it will replicate what the sun does with lighter and darker colors “woven” together, and will look more natural.

I have similar coloring to yours, Anef, and I’ve spent a small fortune keeping my hair “very blonde” over many years. I recently gave up the ghost, and I’ve gone to a medium brown with a few blonde highlights (and some nutmeg highlights). I think without the gradients and without the variation in the tones, the color will look too stark as you go darker. Just my experience and opinion, of course; actual mileage may vary.

If it’s any consolation to you, @JilltheTooth, or anyone else that fears I may turn out looking like Elvira… I do know that I can wear my hair dark without looking scary.
I had to dig for pictures, and it became incredibly clear to me that I have a thing for black and white photos, but I think you get the idea.

The photographic evidence suggests you have nothing to fear. Your dark hair is beautiful!

@picante thanks. I seem to do well with either end of the spectrum, it’s the shades in the middle that tend to make me look really bland. I think. I just feel like brown is a tricky one.

I just came back from my evening out with friends at a place where the the bartender was very flirty just threw that part in for no reason and I notice in the photos that you have lots of shiny stuff in your face, Neffie. I love shiny stuff. Just sayin’

I was going to suggest low lights, but the photo you provided of what you want is a single process. When altering the color drastically while it is already colored, I would recommend having it done professionally. But, if you are going to buy a box at the drugstore, I say try a semipermanent a little lighter than you think you want in a neutral. The photo you provided seemed to have some warm undertones, while you said your natural is ashy (so is mine). Natural Instincts is a semipermanent that comes in reds, neutral and, and ash. Something like that, the side of the box describes it. I just think when the semipermanent washes out over time it will be an easier transition as your natural hair grows back in. However, I have never gone from blond to brown with this product, though I have gone from blond to brunette with my hair stylist using a semipermanent, and I have used Natural Instincts many times on my brown hair and was very happy. So no guarantees with my suggestion, but at worse it will wash out or you can fix it at the salon.

@JLeslie I don’t use drugstore dye, it isn’t true to the shade ever. Ash dyes are almost impossible to buy in a box, because most people would turn their hair green with a true ash. I buy my colour from a beauty supply, and I intend to do a deposit only color to darken my base shade by at least 2 levels, and then I will have a more reliable foundation for the dark dye that I end up going with.
I don’t want warm undertones, and I don’t actually want my hair to look like Liv Tyler’s… I just want to have dark hair and fair skin and not look like something out of a haunted house. :)
At the same time, I want something rich and dramatic – but not shocking or unnatural (in other words, I’m not dying my hair burgundy or black.) I was basically hoping for inspiration or ideas. Brown hair has the potential to be really drab, especially if you don’t want a warm brown, so I’m trying to avoid an end result that is too plain.

@ANef_is_Enuf Some of the dyes are really good at being multi tonal. I once had my hair done on Amelia Island, FL, and it was one of the best colors I have ever had single process. I wish I knew what she had used. It was a medium brown, very rich. I can’t go very dark, or I easily look witchy having a larger sort of pointy nose and very pale skin, so I know what you mean. If you are buying at a salon they should guide you, won’t they? Maybe walk in with a few pics so they know what you are going for.

@JLeslie I don’t go to a salon, either. I just buy from a beauty supply. I expect at least 2 processes, one to darken my base, and then another to apply permanent colour. I’m debating on some highlights to add dimension, but I would wait until I’m sure the darker shade is going to hold before having it highlighted.
I don’t have pics, because I don’t know what exactly I’m going for. That’s what I was hoping to find here today. :)

Yeah, the color could slip out fast. I think that was one reason my hairdresser at the time used semipermanent. It seems the opposite of what someone might do, but it worked out well.