I like both, depending on my mood. High-contrast outfits, like bold black-and-white stripes, feel more dramatic. I love that. I go for high-contrast lipstick a lot, too. But I also appreciate the beauty of a neutral, low-contrast outfit -- all soft greys, for example -- and many days, that's what I feel like wearing.
I'm with Angie in that I don't necessarily think low-contrast people need to wear low-contrast outfits. I've seen plenty of pale, fair-haired women who look great in contrasty looks. My own colouring is somewhere in between -- I have medium brown hair and fair skin, which is fairly high-contrast, but ALL of my body hair -- including lashes and eyebrows -- is blond. I'm not sure why my brows and lashes are significantly lighter than my natural hair colour, as this doesn't seem to be the norm, but oh well. These things are easily fixed with a swipe of mascara and a brow pencil. My eyes are ice green, and the second you put black mascara around them, my natural colouring looks more dramatic. Dark lipstick adds to the effect. So with a small amount of makeup, I feel I have a lot of influence over my own level of contrast before I even consider the contrast level of an outfit.