Beauty 101: Your Lipstick Questions, Answered


This week, our Beauty 101 series is focusing on tips for lips. You had questions, and your fellow commenters have the answers:

As always, I thank all of you for emailing and posting your tips and tricks, and I apologize that I’m not able to use all of them, due to space issues. There are hundreds of lipstick related tips on yesterday’s post, so be sure to go through it for additional hints and such. And now, a few lip tips from your fellow readers:

On Applying Red Lipstick:
From commenter grace darling:

Here is my four-step process for applying perfect red lippy. It’s not highly scientific, but it is very easy.
1) Exfoliate. As with any cosmetics, you need a smooth canvas before you apply any paint. Scrub lips gently with an old toothbrush or some oil-and-sugar mix, then wait until the tingling feeling has subsided to move on to the next step.
2) Prime and line. Slick on some waxy balm or a lip primer – MAC makes an amazing one, but my Mary Kay cheapie also works pretty well. Wait for the primer to dry. Line the outside of the lips with either a nude or invisible liner – this is your safety net for ultra-long wear. Then follow your natural lip-line with a liner that matches your lipstick. This doesn’t have to be perfectly precise, for reasons that will become apparent. Gently fill in the lips with liner. Just kind of roll the side of the pencil against your lips and you’ll be fine.
3) Fill in the colour. Now, take a lip-brush (again, a cheap one works fine) and start applying layers of colour. If you’re a rosy-tint kind of gal, skip the lip-lining step and just mix a bit of lipstick pigment with some lip-balm on your brush. This will give you a sheer, diluted layer of whatever lipstick you choose. For a bright, matte look, just keep applying lipstick, blotting between each layer, until the lips are pigmented enough. Blot again.
4) Line again. Now, this step is really for those of us who are clumsy in our initial applications or super-paranoid about long wear. Remember how you didn’t have to care about getting a perfect outline in the first go? That’s because you’re going to take your liner, sharpen it, and outline your lips again, with your elbow propped up and your face very close to the mirror. Re-lining lets you fill in any gaps and really lets you get a sharp, precise lip shape.
This whole process, when you’ve practiced a couple of times, takes about five minutes. It makes you look instantly ‘done’. Throw on some matte powder and brow liner (before your lipstick, of course) and you’re practically ‘polished’.

From commenter LadyCoCo:

Foolproof red lips step-by-step:
1. Condition your lips. Healthy lips are going to keep lipstick on way longer, so put on a rich balm or salve before you go to bed, if possible. I like CO Bigelows rose salve; it’s really moisturizing. If you don’t have time to wait a whole night, dab a little eye cream on your mouth; it has way more moisture than anything made for the lips.
2. Prep. When it’s time to apply your lip, start out with a waxy (not slippery) balm. The original Burt’s Bees peppermint-smelling stuff is ideal. Then dab on a lip primer if you have one; if not, eyelid primer works equally well. If you have to, you can usually skip the primer if you’ve moisturized well enough and applied a good waxy balm, though.
3. Brush on color working from the outside in. Shu Uemura’s $35 kolinsky lip brush is supposedly the best, but I find that just about any lip brush works about the same. It should have medium-firm bristles, but size is the most important quality in a good lip brush. It should be small, not wide, so that you’re not tempted to go outside the natural lines of your mouth. You should never do this, no matter how thin you might think your lips are.
4. Line your lips with a lip liner in a matching color. Lip liner seems to have fallen out of favor in recent years, but it’s really the key to a polished red lip. Line carefully and slowly within the natural line of your lips-don’t draw anything outside your lip line. Some people may find it easier to draw light dashes, then connect them.
5. (Optional) Slick on a red gloss like NARS lip gloss in Bloodwork. This will keep your red lip intact all day and add a sexy, vampy effect.

From Vivien, via email:

The picture you used says it all, red lipstick needs to be applied with a brush in order to have that perfect shape. Here are the general steps I have been following since I was 14 and learned from Kevyn Aucoin Making Faces.
1. Exfoliate lips (toothbrush works great)
2. Moisturize lightly, maybe even blot off the chapstick otherwise the lipstick will not stick.
3. Lightly powder the lips for extra staying power.
4. Using a neutral lip liner follow the natural shape of the lips, going slightly outside the line for extra fullness if desired.
5. Fill in the lips with liner and blot, softening the edges with a tissue if the shape looks to harsh.
6. Using a lip brush apply lipstick evenly all over the lips, blot.
7. Dust the lips with loose powder, blot.
8. Again with lip brush apply lipstick evenly over mouth, blot.

On Picking The Right Red:
From commenter thegoddessfoo001:

When it comes to red lipsticks, there are three different genre’s of color that I have encountered while working with them. There are the blue and yellow/orange (what ever you have heard it called) based colors, then there are true reds. I use orange reds and true reds. Finding a true red is like finding a needle in a hay stack, but they are out there, just generally a little more expensive (in my experience). Ask an artist when looking for a red, and go to a counter worker! I say that because the vast majority love what they do, know colors, and try to make sure that you know how to distinguish between the colors.

On Getting Lip Color To Last:

From commenter footnotegirl:

First, if you really want lasting lip color, your best bet is to get a more expensive but more highly pigmented blend, or to purchase a lip stain. These will last much longer than your average bear. There are also the ‘long lasting’ lipsticks but I find they end up looking like I have a plastic coating on my lips and just. Gross.
With stain, you apply it in thin layers and there’s no need to blot. This should last a good long while, especially if you avoid fatty food.
If you want a non-stain to last, the long-form is to put on a thin layer, blot and lightly powder, then another layer on top of that, blot again.
I also get good results by buying a lip liner that is the same shade as my lipstick (or a hint darker), applying it all over the lips, and then putting a thin layer of lipstick on top of that and blotting.

From commenter Friday:

When I wear bright or dark lipstick (which I do often when I’m going somewhere special) I use the following process to get it to stay on and look neat.
First of all: the texture of the lipstick will either help or hinder its staying power. If you want real warpaint that’s going to stick with you for more than four hours, go with a creamy or matte lipstick. Anything glossy will go the way of most lip glosses, i.e. it will disappear.
Second: get a lip liner, and get a good one. The ideal lip liner should provide opaque color, be easy to draw on, but not so soft that it can’t hold a point when you sharpen it. Ideally it should match the color of lipstick you’re applying. In a pinch, though, you can use something of a similar color family. I own a single red lip liner that I use when I wear bright red, darker red, and even fuschia or coral lipsticks. Do NOT, I repeat, DO NOT use a lip liner darker than the lipstick you are using. Unless you’re going for a “throwback to the worst of 90’s fashion” look.
Third: Apply said lip liner. Using a good mirror (I like a larger compact so I can hold it really close to my face) and holding the lip liner like a pencil, draw a line around the shape of your lips. Go slooooooooowly. I start in the middle of each lip and work to the outside, and then repeat on the opposite. You want to stay just on the border between your lips and your face or just over that line. When in doubt, be conservative. Too far over, and you’re getting into clown territory! After you’ve outlined your lips, then fill them in with the liner. I usually angle the pencil and use the side to provide a wider stroke of color to fill my lips in.
Fourth: apply your lipstick. Ideally, with a lip brush, but realistically, apply a thin coat. Carefully. You want to stay just inside the lip liner, because that will keep it from bleeding. Then, use a single ply of tissue to blot your lips. Apply a second thin coat of lipstick. Blot again. Voila!
Bonus round: Take a clean single ply of tissue and lay it over your lips so that it sticks to the lipstick. Use an old powder puff to press translucent powder onto the tissue, then remove the tissue, and use a new tissue to blot off the excess lightly. Although this can make your lipstick feel heavier and thicker on your lips, it really helps to keep the stuff on.

For Rosy Lips:
From commenter sach-bot:

Here’s a tip for creating rose-bitten or a more natural, tinted lip color.
For daily wear like running errands or going to school, I don’t like to wear full on lipstick or gloss. Yet, I do like to have some color on my lips so I do the following:
1. Exfoliate lips – moisturize lips the night before (I find an AHA-based lotion to be helpful in exfoliating away dryness while I sleep). You can also apply a scrub with a soft toothbrush or your fingers in the morning if needed.
2. Apply a day cream with SPF to lips, corners around the mouth, and the area outside the lip line.
3. Pick a dusty rose or mauve colored lipstick in a hue that complements your skin tone. Since I have medium skin tone a la middle eastern/south asian, I prefer MAC’s Plumful. It’s a rose plum with just a hint of sheen.
4. I dab lipstick onto my index finger either directly from the lipstick or lip brush (more hygenic). I rub the color onto my bottom lip and dab and rub more of it onto my top lip. Start from the middle of the lip and then outward.
5. Purse lips and blot any excess color.
6. Clean any color that bleeds out or use a nude reverse lip liner in your skin tone.
7. Rub a little vaseline onto your lips to add sheen and make it longer lasting.
I like doing this a lot for when I want to keep it soft and simple.

On Avoiding Lipstick On Your Teeth:
From commenter gracedarling:

Close your lips around your index finger, and then pull the finger out of your mouth. Sounds dirty, but it gets all the excess pigment out of the centre of your lips (where it’s likely to transfer to your teeth).

On Keeping Lips Soft:
From commenter CKD1:

Believe it or not, you need to exfoliate your lips, too, if they get too chapped or dry. Couple of different ways: rub a warm, wet washcloth on your lips (gently!) and after you dry them put on some Vaseline or Aquaphor and let them heal. Mary Kay also makes a Satin Lips set where you rub on a scrub/mask, rinse it off & apply lip balm. If you do this at night you’ll wake up with soft, hydrated lips, which makes lipstick, gloss, whatever go on and stay on much easier.

From Elizabeth, via email:

First, if your lips are chapped, or are flaking, gently brush them with a clean wet toothbrush. Then, apply a little bit of lip chap; not too much, just enough so that your lips aren’t dry. Don’t put on the lipstick immediately after the chap, otherwise it’ll get messy. Give your lips about 5-10 minutes, enough to let the lip chap sink in.

On Dealing With Extremely Dry Lips:
From Megan, via email:

I wanted to pass along some lip tips for people prone to dry lips and have recurring lip issues (cold sores, fever blisters, cracked, chapped, etc) or sensitive lips:
Preventative – Take Lysine daily, as a supplement. I used to get cold sores all the time, but since I’ve started taking Lysine I maybe get one every two years and the severity/length of the issue is super improved. If you tend to get cracks at the corners of your mouth add Vitamin E as a supplement. You can take it in pill form or use the Vitamin E oil and apply it to the damaged areas, during a flair.
Exfoliate – Washcloths are great for exfoliating your lips and helps keep them soft. You can also try the lip scuff from The Body Shop, as that is a fun lip scuff that lasts forever and does well at exfoliation.
Best Lip Moisturizer – Aquaphor is the best moisturizer for your lips – ever. It is inexpensive, easily accessible (generally in the lotion aisle, made by Eucerin) and leaves your lips soft and moisturized without feeling greasy or wonky. I use it every night (used to use Vaseline) to keep my lips hydrated and soft, but it works overtop of lip color for a glossy affect.
Long-lasting Lip Color – Revlon Colorstay works really well for me and they have a great range of colors – best bang for the buck in my opinion. I’ll apply it in the morning and it lasts through the work day without making me look like Ms. Geist. Every once in a while they leave my lips feeling sort of dry, so I’ll abstain wearing the Colorstay for a day or two and exfoliate and I’m good as new, with no issues (BTW – I’m kind of comma crazy and not the best at using them, so my apologies if that last sentence made your head spin)
Chapstick Replacement – Nivea has a line of lip stuff that is a tinted lip color – like Cherry Chapstick on steroids. It gives good color (and there is a range of flavors/colors), without it being overwhelming, is moisturizing and has a great smell/taste….super fun for smooching.
Avoid – I can’t use the medicated lip balms, as they make my lips peel and feel really weird. I try to limit having tons of citrus and salt, as they can make my lips have a flair up. However, if I house a bunch of edamame, doused in salt, I just make sure I clean my lips immediately and add a dose of Lysine and use Aquaphor a lot.

On Using Lipliner:
From commenter ceejeemcbeegee:

Choose a liner color close to the shade of lipstick/gloss you are wearing, or just a shade darker. No more dark liner and light lipstick!
I hold the pencil like a real pencil, like I’m writing. I place my pinkie on my chin to steady my hand and start with my top lip in the center peak and work toward the edges. The key is to use short strokes: don’t try to do one long line. On the bottom lip, I start from the outside in. I have full lips, so I don’t line the bottom lip all the way around, just from the edges to half of center on each side.
Lip liner isn’t a requirement, but it helps create definition if you wish to make thin lips look fuller, or if your lipstick bleeds. A lip primer helps with the bleeding.

From commenter NeonClaws:

How to make your lipstick last for hours AKA How to line and fill your lips with lipliner.
To make my lipstick last all day, I color my entire lips with lipliner and then put my lipstick on top of that. I’ve been doing it this way for years and although I was akward at first, I can promise you practice makes perfect.
Here’s my tips:
1. Use a lipliner that matches your lipstick. This is incredibly important. You want to create a seamless color on your lips, not some two-tone craziness.
2. Sharpen your lipliner every time you use it. A fresh point on your lip pencil will make it easier to apply and give you a more defined lipline. For this reason I stay away from self-sharpening pencils. That little tube of color that gets pushed out by a self-sharpening pencil will always be duller than the freshly sharpened point of a pencil made of wood or wax. Between wood and wax pencils, I prefer much wood. I think you can sharpen a wood pencil better than a wax one.
3. Steady your arm and your mirror. Sit at a table and put your elbow down on the table top. Use a free standing mirror so you don’t have to hold it up. Use a mirror with magnification if you want. Hold the lipliner in your hand as you would hold any normal pen or pencil. Use the hand that you write with.
4. Smile. This will pull your lipline a little taut and make it easier for you to trace the shape of your lips with your pencil.
5. For the bottom lip: Start at the center and work your way out to the edges. It is easier to draw the line in short strokes. Follow the natural line of your lips. Don’t line outside of your lips or try to change the size or shape of your lips. Yes, it is possible to do this and an experienced person can reshape a lip line and make it look natural (with the use of concelear, powder, lipliner, etc.) but for most of us, trying to change our lips’ natural shape just makes us look sloppy and/or ridiculous.
6. For the top lip: If you have a defined cupid’s bow – start in the middle, draw a stroke up for the peak and then draw a stroke down. Draw the peak a little soft and rounded for a more natural look. Keep drawing little strokes until I reach the corner of your mouth. Repeat for the other side. If you don’t have a cupid’s bow, lining the top lip will be much like lining the bottom lip.
7. Fill in the lips with the pencil. The way to do this is to rub the sides of the pencil tip against your lips rather than trying to fill in your lips with the point of the tip. Did you ever “sharpen” a crayon as a kid by rubbing the tip on a piece of paper at an angle, to shape the tip back into a cone? This is essentially the same technique for filling in your lips with the lipliner pencil.
Hold the pencil with the tip pointing up. Press the tip to your lip. Rub the sides back and forth across your lip, being careful to stay inside the lines.
8. Lay your chosen lip color on top of your lips. It’s better to apply with a lip brush (especially if you’re dealing with a bold color) because you can be more precise and it will help keep you from smudging your lip line, but I often apply my lipstick right out of the tube.
9. For extra long-lasting color, wait a couple of minutes, blot your lips, then apply another coat of lipstick.

And Perhaps Most Importantly…:
From commenter ASmallTurnip

Wear what makes you feel good. That’s always classy.

Didn’t get the answer you were looking for? Be sure to check the original thread, which is filled with tons of advice from your fellow commenters. Disagree with something you see here? Feel free to set the record straight in the comments. And as always, suggestions and questions for next week’s Beauty 101 column are always welcome.

Earlier: Beauty 101: “I Fail At Keeping Lipstick On My Mouth”
Beauty 101:Your Hair Questions, Answered
Beauty 101: Your Waxing/Shaving Questions, Answered
Beauty 101: Your Foundation And Concealer Concerns, Answered
Beauty 101: Your Eyeliner Woes, Solved

Inline Feedbacks
View all comments
Share Tweet Submit Pin