For the simple reason that I feel it is very easy to look dated & tacky in makeup that goes full on matchy-matchy. It is better to just complement your outfit instead.
Complementing means that you stay within the same warm or cool tones. Generally.
So if I were wearing a burgundy colored Indian outfit, I would opt for deep copper toned eyeshadow and would pair it with a deep rose toned lipgloss.
If you wear mostly neutral colors (brown, beige, grey, black or white), a purple or khaki or charcoal grey eye shadow would be great with lips shaded in a natural tone of lipstick, alternatively, you could also do simple neutral eyes with a deep red lipstick.
Gold eyeshadow tends to look really good on Indian skin, so you can use it with most colored Indian outfit.
For western outfits, a fool proof selection is soft brown to dark brown, or grey and make it smokey, if it is night time, pair with a rosy lipstick. Also if your outfit is sexy, keep your makeup simple.
Ok, let's say you still wanna match your outfit - then choose between the eyes or the lips & match only one of them to the outfit. If you are wearing a dress that is blue & pink - don't wear blue on the eyes & pink on the lips & cheeks. Decide between one - either do blue eyes with a nude lip or neutral eyes with lots of mascara & pair it with a bright pink lip.
The only exception I make is when I wear earthy, metallic tones like copper, bronze colored outfits
But these are just some rules I follow, I do know of some people who do wear matchy-matchy makeup & look gorgeous in it. But then they would look gorgeous even with mud on their face. :-)
So what are your tips for dressing up? Do you match your outfit to your clothes?