I get asked a lot which to apply first, the liner or the lipstick. The answer is... it doesn't really matter. Just try both and see which works best for you. Below is personally my favorite way to apply a red lip. I've tried many different ways and this is what works best for me!
I think the most important thing to do when wearing a red lip (or any bold lip color) is to really work the pigment into the skin. If you just slap on a lipstick and go, it probably won't hold up too well.. I find that starting with hydrated and EXFOLIATED lips makes a huge difference. Nothing is less attractive than dead skin hanging off your lips... so use a lip scrub or use a hand towel or Q-tip to gently exfoliate your lips. I like to use my Clarisonic brush for this, or the Sarah Happ lip scrubs (they are delicious!).
Once your lips are exfoliated dab on a little lip balm. Not so much that your lips are dripping with it, just enough to moisten them up a bit. Give the balm a minute to sink in, then begin applying the lipstick (you may need to blot first if you put on too much lip balm).
Step 1) Work the lipstick into the lips using a brush. I like Chanels Rouge Allure lipsticks (like Passion or Pirate), and quite a few MAC lipsticks (Ruby Woo or Russian Red) as well.
Step 2) Blot with a tissue once or twice.
Step 3) Line the lips with a matching lipliner and fill them in a bit with the liner. I really like the Chanel lip pencils because they have a lip brush on the end that you can use to blend the liner and really work the lipstick into the lips.
Step 4) Then apply a second coat of lipstick with a lip brush. Really work it in and get it perfect.
That's it! It should stay on for a few hours then you'll have to touch up.
If you want to add a gloss you can, just keep in mind that it will make the lipstick bleed and come off a lot faster. The more you layer on the lipstick, blot, layer on lipstick, blot... the longer it will last. When you blot you are removing the moisture but the pigment stays in the skin. How many times you want to do that is up to you though. Once is enough for me :)
Here is video from one of my favorite makeup artists on how to do the perfect red lip.
Still need more help?
Here is the ultimate guide to red lipstick.
MUAH! xoxo!