Okay, so the jacket is fug-worthy, but I just had to post this picture of Shohreh Agdashloo - whom Spirit Fingers dubs "The Iranian Catherine Zeta-Jones (without the grandpa-husband)" - to illustrate how red lipstick works for those of us with dark hair and dusky skin. From this picture you can see that the red is a bit on the brownish side - not too dark to wash her out, not too blue so as to clash with the skin tone, and not too orangey so as to age her.
In real life, however, it is difficult to find a very complimentary red lipstick without having to try so many others that, well, aren't. Take it from someone who used to wear her makeup like Robert Smith: You don't want to look like the living dead with red lips of any kind. Nor would you want to look like a cartoon character, a porn star, or a frequent shopper at Hot Topic. (No offense to any cartoon characters, porn stars, and/or Hot Topic shoppers in the audience.)
I stumbled upon the secret to wearing red lipstick not too long after I got my first tube: You have to start with a neutral lip pencil, to outline the natural shape and then fill in the lips completely as a base. Once you do that, it doesn't matter if you put it on with your finger, a brush, or straight from the tube, as long as you use a light touch. Make sure to stay inside the pencil lines and blot after every coat with a tissue, to make the color stick. You don't even have to powder on top of it, unless you want your lips to pucker and hurt after a few minutes.
So, on to the recs:
High end: Seriously, if you want a very good red lipstick, you might as well spend good money for it - which is why I am very (almost insanely) partial to MAC. My current red, in fact, isn't even a real "red" - it's MAC Underworld, which is more of a dark brownish burgundy. Another great high-end option that I've tried is Fresh's Rouge Catalan, which I wore in my last few years of college. And though I've yet to own any lipstick from this brand, I think Nars has a great selection; in fact, I believe that Nars Congo Red and Shanghai Express are the most beautiful red lipsticks, ever, and the matte formulations are the least bit drying. High-end brands are also a good place to look for long-lasting formulations, and Smashbox makes a really nice one in lovely shades of red.
Discount: Of course, if you can't spring for the pricey stuff, your next best bet would be the Sephora Collection - the formulations are just as nice as the others, for less cash. But if your shopping preferences and budget lean more towards the drugstore side of things, you might as well shop judiciously - and stick to the traditional lipsticks rather than the long-wear ones, which tend to be more drying and atrocious in texture. (And, no, I have yet to try out the newer formulations - I'll have to tell you those horror stories later.) For this reason, I love, love, love Maybelline Moisture Extreme - the range of red shades alone is not only impressive, but wildly flattering to any skin tone and mood. (Hello, Toasted Almond and Red Dawn!) The newest versions of Revlon Super Lustrous lipstick are also beautiful - not for nothing does Julianne Moore sport their red shades in the ads, because it does stay creamy and lush for hours. Finally, if you must: The NYC line (in your better drugstores) has a few but fabulous red shades that last as long and stays as nice as the other brands.
Go-withs: Attitude, of course- no use wearing it if you're going to scowl for hours. Also, unless you want to look like a particularly scary office lady, skip the pale matte powder and the harsh black liquid liner all around your eyes. The lips look best with fresh skin - a dewy liquid or mineral foundation would work - and a slightly shimmery blush or bronzer that matches your natural flush. I've also found that neutral but shimmery shadows in the bronze/taupe/champagne range will balance out the lips to avoid the Goth-girl effect. Lashes must also be full but natural; wear falsies if you must, but you'd just be as good to go with a non-fiber-formulated curling/volumizing mascara.