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Updated Jul 29, 2016 @ 1:15 pm
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Credit: Brian Henn

Lipstick seems straightforward, but it can actually be an accident waiting to happen (e.g. my first attempt trying to eat while wearing red lipstick). I wish there had been an elective in high school about how to apply the makeup basics (I would definitely be using those skills more than my knowledge of blueprints and drafting), but unfortunately, that didn't exist for me.

We as humans are expected to just know how to pick and apply lipstick, but, sadly, these things are not second nature. It's not like breathing or blinking—these functions are not genetically linked to our DNA. So here's a lipstick guide—a little black book of bold mouths, if you will—on how to get your lipstick right the first time.

Pre-Lipstick Prep

I start by exfoliating my lips, especially if I'm going to wear a bold color. The pigment in deeper shades tends to get stuck underneath any dry patches on my lips (even if they're invisible before applying the lipstick). Lately, I've been using the Clinque Sweet Pots in Black Honey. I love that one side is an exfoliator and the other is a lip balm. If my lips are particularly dry, or if I'm using a liquid lipstick, I'll apply a tiny bit of the balm and blot off any excess with a tissue before applying any other product.

Picking Your Lipstick

When choosing your lipstick, first decide if you want it to be more glossy, more of a natural finish, or more matte. Glossy lipsticks reflect light (hence the word glossy) and can draw more attention to the mouth, allowing lips to look fuller. Matte lipsticks absorb light and are great for those with naturally fuller lips that are trying to deemphasize their pout. They are more long-lasting but can also dry out the lips as a result. Natural finishes are ... natural. They're not super-matte, not super-glossy; they mimic the texture of your actual lip. There's also metallic, satin, shimmer, semi-matte, cream, and loads more.

Did you pick the type of finish you're looking for? Good! Now decide how sheer or saturated you want your lip color to be. Do you want something translucent with a wash of color, where you can still see a hint of your natural lip color through it. Or do you want something opaque, where you can only see the lipstick color and no natural lip tone.

Did you choose a level of saturation? Great! Now let's decide on the actual color. If you have warm-toned skin, choose a warmer lipstick like orange, golden nude, orange-pink, or orange-red. If you have cool-toned skin, choose a cooler lipstick, like blue-toned pink, greige, blue-red, or cool purple. If you're neutral, the world is your oyster! But don't forget, the rules are just that: rules. And rules are meant to be broken. Sometimes, using a cool-toned lipstick on warmer skin can really make the lips pop. Sometimes a lipstick can be textbook perfect for someone, but if he or she is not used to that color, it won’t feel right to the wearer. My best advice: Try on the lipstick. If you love it, buy it! If you don't, don't.

Application method

OK, so we found our perfect lipstick. Huzzah! Now let's decide if we should use a lip brush to apply it or apply it straight from the bullet.

Here’s what to consider.

Lip brushes:

  • Give sharp definition and more precision. In some cases, there is no need for lip liner.
  • Even saturation.
  • Less lipstick on your teeth.
  • More control.
  • Can do an ombré effect.
  • Much easier to apply with a brush than the bullet on someone else.

Lipstick bullet:

  • Easier to carry it with you.
  • Have to have a steady hand (less of an anchor point).
  • Easier to touch up with.
  • Easier to build up saturation quickly.

Personally, I’m a lip brush girl. Sephora has a fantastic portable, retractable lip brush for just $10. When applying lipstick with the brush, I start by working at the center of the lips and work out to the edges. I define my lip line first and then fill inward. If you accidentally use too much lipstick, you can clean up the edges with a concealer or blot any excess away.