Actually, all the girls in my high school (in the late '80s) used Clinique too. (Well, except for the “Wet’n’Wild” bunch. 
) Anyway, I guess it is a brand beloved by teenagers, but not used by them exclusively.
I’m very fair-skinned, also, but I have very dark brown hair and eyes, so that always throws the girls behind the counter. They look at my dark hair and assume I need something ruddy. I know exactly what you mean about disasterous make-up sessions!
I use the Clinique “Stay True” formula, in the ‘Stay Ivory’ color. Its number is 01, so I would assume it is the lightest shade, but there could be something numbered 00, which would be even lighter. Don’t try it on the back of your hand. The back of your hand is completely different from your face.
Ask for some samples to try at home. If they want you as a regular customer, they will be willing to let you try the stuff before you shell out big bucks for it. See how you look in daylight and in your own bathroom light.
I just use it very lightly under my eyes, on my chin, and on a few imperfections, like a little broken capillary on my cheek, which is just a little red veiny-looking thing that I like to cover up. Keep it simple and you won’t have that “made-up” look.
If you need to wear foundation go to a Prescriptives counter. They will match the foundation and powder to you exact skin color. You should always use a wedge to apply your foundation.
Blush, eyehadow and lipstick depends on you skin tone. There may be colors you should stay away from. The only way to really find out is to try it. You might want to get someone else’s opinion other than your own before going out into public.
For foundation and powder go Prescriptives.
For lipstick, blush, and eyeshadow I suggest Christian Dior or Este Lauder.
For mascara I suggest L’ Oreal.
For eyeliner definitely Cover Girl.
You guys rock.
I’ll update this thread after finals when I have some lazy summer days to play with this stuff. I work at Rite-Aid so the drug store stuff I get at a discount and can return without hassles.
Fancier stuff, I['ll ask for samples as you have suggested.
One step closer to being a real live girl.