Should You Match Your Makeup to Your Outfit?

Sometimes it works... and sometimes it's a massive #beautyfail.
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Michelle Villett
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Sometimes it works... and sometimes it's a massive #beautyfail.
Selena Gomez, Perez Hilton Blue Ball

I may have come down hard on Milla Jovovich last year for going hog wild on the orange (dress, eyeshadow, blush AND lipstick)... but in general, I like when things match. You know, like bras and panties. Shoes and handbags. Bacon and eggs. It helps one make sense of the world.

So that's why I'm torn on the topic of whether you should match your makeup to your outfit. For every instance where it looks terrifically chic, there's another where it's a bit too... considered. Sometimes the surprise of a contrasting colour on the eyes or the lips just elevates the entire outfit, in that "I just threw this on but of course I always look this gorgeous" kind of way.

And so, with helpful visual aids, I've compiled some guidelines on the whole matching subject. Obviously Selena Gomez, above, is demonstrating Rule #1: If your lipstick, eyeshadow, eyelashes, hair accessory and faux tatts are ALL the same colour as your dress, the calendar had better say October 31st.

Here are the rest!

A soft wash of colour on the eyelids is usually a safe bet.

Eliza-Dushku-Perez-Hilton-Blue-Ball

This is Eliza Dushku, who also attended Perez Hilton's "Blue Ball." (Okay, maybe we can give Selena a pass.) But still—isn't this a much better way to do the matching thing? The shadow is so close to a grey that it's almost a neutral, but it still gives that little bit of unexpected pop.

With fuchsia and orange, match your lipstick to your skirt, not your whole outfit.

Jennifer-Hudson-fuchsia-lipstick

This strategy kinda gives you the best of both worlds—the stand-out factor of a bright lip against another shade in your top... but the tying-it-all-togetherness of wearing a colour that is elsewhere on your person. Check out the close-up of Jennifer Hudson, above, and the full head-to-toe, below:

Jennifer-Hudson-at-AOL-sessions

Compare this to the head-to-toe fuchsia worn by Paris Hilton:

Paris-Hilton-hot-pink-lipstick-dress

With the headband and the dress, did she really need the matching lipstick as well? Nein, Paris. As for orange, the best guideline for what NOT to do is this pic of Milla Jovovich:

Mila-Jovovich-Hollywood-Awards-Gala-3

Yes, some outfits really DEMAND a nude lipstick.

The exception to red lipstick. Match away!

Selena-Gomez-2011-Disney-Kids-and-Family

Unlike fuchsia or orange, red lipstick is truly a classic—and so, you can get away with the matchy-matchy thing a lot more here, as Selena Gomez so gamely demonstrates. (MUCH better this time, Selena. Blue is so not your colour.)

And of course, it goes without saying that soft pinks and peaches look great with everything.

Fergie-36th-birthday

How amazing does Fergie look here?

Sometimes introducing a brand new shade into the mix is exciting! And beautiful!

Cameron-Diaz-pink-lipstick-red-dress-Green-Hornet

Sometimes red with red is just too predictable. This is probably my favourite look of all—pink lips with a red dress, on our good pal Cameron Diaz. I think it works a bit better than Mandy Moore's lavender lips with an orange shirt...

Mandy-Moore-Virgin-Mobile-Canada-event-2011

... although she gets 10 points for trying.

When wearing a multi-coloured print, pick up one (or more) of the colours.

PFW-F11-Emma-Stone-Louis-Vuitton

Any excuse for me to throw up this pic of my current girl crush, Emma Stone. (She shares that distinction along with Amy Adams and Christina Hendricks, of course.) I'm just crazy about her makeup here, which picks up the colours in the print side of her dress.

Emma-Stone-dress-at-Louis-Vuitton-2011

Still—doing both eyes AND lips is a look that requires some skill (and confidence) to pull off. Otherwise, it's probably safer to pull out just one colour for the lips, like Carla Gugino does here with this spectacular orangey red:

Carla-Gugino-lipstick

If your name is Blake Lively, then no, peach eyeshadow does NOT "go with everything."

Blake-Lively-Nov-2010

But we've talked about that before, haven't we?

So tell me:

Do you always match your makeup to your outfit?
How do you feel about throwing in an unexpected shade just to mix things up a bit?
Which one of these celeb makeup looks do you like the best?