How NOT to Wear: Lipstick and Lipliner

We’ve all seen “How to” posts regarding how to apply makeup, but not that many “How to not” ones. I thought this might be fun and helpful because I sometimes learn backwards. Meaning if I know what not to do, it helps me realize what I should be doing. Make sense?

Lipliner No No’s

A big trend in the 90’s (ala Pam Anderson) was to wear a dark lipliner with a lighter lipstick and not really blend a whole lot. This was never a good look even back then, but it’s SO dated now.

For reference I am wearing MAC Masque lipstick with MAC Spice lipliner. This is a bit exaggerated, but I HAVE seen people wearing looks like this!

Bad Lipliner
Unblended lipliner

Bad liner 2
Unblended lipliner

Now I don’t necessarily think Spice is too dark for Masque lipstick, but it does need to be blended in quite a bit so there is no obvious line between the colors.

I used a small lip brush to kind of feather the liner out into the lipstick so it blends it in. Also adding another swipe of the lipstick over everything helps meld it all together.

Good liner
Blended lipliner

Good liner 2
Blended lipliner

Now along the same lines as not blending your liner is the “ring around the mouth” effect which happens when you only line the edges, and the lipstick in the middle of your lips wears off. So not attractive.

To avoid this effect line your entire lip with the liner then apply lipstick over that so it wears off evenly. That or make sure to check your lips often and reapply lipstick!

Worn off lipstick
Ring around the mouth

Worn off lipstick 2
Ring around the mouth

Overdrawn lips

If you have slightly uneven lips, which most of us do, it’s fine to correct that. However this can get way out of control. I have seen people walking around with hugely exaggerated lips and it just winds up looking a bit comical, and very obvious and unnatural. Like this woman I came across on the web…


Source

That is obviously an extreme (and Photoshopped) picture, but you get the idea! So try not to get too crazy with the overdrawing. A good way to tell if it looks weird is to look at your lips in a mirror from the side. If your lips look weird and unnatural chances are you overdid it.

For reference I am wearing MAC Russian Red lipstick and MAC Cherry lipliner.

Overdrawn lipstick
Overdrawn lips

Overdrawn lips 2
Overdrawn lips

Overdrawn lips 3
Overdrawn lips

Lipstick on teeth

Blot, blot, blot! Remember when you are wearing a really dark or bright color especially, it’s super important to blot so you don’t wind up with it all over your teeth.

Not only do I blot, but I smile to see if any more gets on my teeth, then I blot again and repeat until nothing is on my teeth. Red can be the worst culprit and the most obvious.

Lipstick on teeth
Lipstick on teeth

Lipstick on teeth 2
Lipstick on teeth

Here’s how I wear my red lipstick. See, no unblended lipliner, no lipstick on teeth and just a little overdrawn to even out my cupids bow area.

Good red lipstick
Normal lipstick

Good red lipstick 2
Normal lipstick

Good red lipstick 3
Normal lipstick

Well I hope that was somewhat helpful to you guys and entertaining as well.

Let me know if you liked this post in the comments and if I get a good reaction from you I will continue with other ones!

-Kelly

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82 comments

  • August 22, 2011
    Kira

    *shudder* The overdrawn lip lady will haunt my nightmares…

    • August 22, 2011

      Hi Kira,

      Haha!

    • August 28, 2011

      Me too!!! I think I need therapy after this one…hahaha!!!

  • August 22, 2011

    Haha, great post! Red lips look stunning on you. ♥
    AmyGrace´s last post…Dots ‘n’ RosesMy Profile

    • August 22, 2011

      Hi AmyGrace,

      Thank you :)

  • August 22, 2011
    Gina

    Oh man, I work in cosmetics at Macy’s, and I’ve seen some crazy things. If you think your picture with MAC Spice and the lighter lipstick was over-exaggerated, think again. I saw a woman yesterday with dark purple lipliner, and that was it. No lipstick to fill it in with at all. I felt so bad, because I couldn’t stop staring at her lips. It was just so bad.

    • August 22, 2011

      Seriously? Hahaha! That sounds like such a crazy look. At least you were able to compose your self because you were at work. As an onlooker, I might not have been able to stifle my laughter. (I’m mean sometimes…but honest.)
      Swatch And Learn´s last post…Nail Art Tutorial: Ladybug NailsMy Profile

      • August 23, 2011
        ReaderRita

        OH! For a while (several years ago) I used to see all the teenaged girls who rode the train wearing BLACK lipliner with what looked like clear gloss!!! Add that to over-plucked, over-penciled eyebrows, and it’s a recipe for beauty disaster! So unnatural and harsh. I never saw a bunch of natural women who looked more like drag queens in my life. But I guess if they felt beautiful, it didn’t matter what I thought…

  • August 22, 2011

    Haha That’s a great comical way to breakup otherwise mundane everyday how-to makeup tutorials. I liked it! Very original!

  • August 22, 2011

    Gotta be honest, lipstick on the teeth kinda grosses me out :) But, I did enjoy this post, particularly that you included the right way to execute the different “don’ts” you talk about!
    ABC´s last post…Awesomesauce Friday {8/12}My Profile

  • August 22, 2011
    suzanne

    perfect post! hope that it’s seen by many ladies, especially those that are guilty!

  • August 22, 2011
    Micki

    YAY! Finally some info/tips for those who wear the dark liner and lighter lipstick! I either wear the same color as my lipstick liner or a a liner that matches my natural lip color. I also hate when they over draw their lips with lip liner! Thx.

  • August 22, 2011

    I’m like you – find it very helpful to find out what TO do by seeing what NOT to do. (That’s why I used to love that TLC show, What Not to Wear.)

    Hehe, you’re brave, Kelly, to post those photos of you with lipstick on your teeth! It’s all in the name of helping others, so I applaud your courage. ;)
    Swatch And Learn´s last post…Nail Art Tutorial: Ladybug NailsMy Profile

  • August 22, 2011

    Do you have any good recommendations for a good lip liner? I haven’t been able to find brands that I like that are also under $15.
    The Lacquered Lady´s last post…OPI By Sephora Fall Collection Mini ReviewMy Profile

    • August 22, 2011

      Hi The Lacquered Lady,

      Most of mine are MAC and Stila but I also really like a lot of ones from Revlon, which are less expensive.

      • August 22, 2011

        I’m always lusting after the Stila packaging, but have never tried their products. I’ll have to give it a try!

  • August 22, 2011

    This was a great post, what a fun read!! The lipstick on the teeth photo, love!!

  • August 22, 2011
    Sophie

    Good post! I usually just use a nude lipliner under my lipstick…
    For the lipstick on teeth I have a good trick! After applying lipstick i put my finger into my mouth and close my lips on it and then pull the finger out. It iusually removes the lipstick thats too much inside the lips (if that makes sense).

    • August 23, 2011
      ReaderRita

      Yep, the “finger trick” really works!

    • August 23, 2011
      Corey

      I also use the finger trick. I’m sure I look oh-so-classy, but it works so well. :D

  • August 22, 2011
    meme

    Love your red lips! This AM on QVC there was an hr from Smashbox. They have a match your skin tone pencil – only 4 shades anyone would ever need. Advice is to only use a liner that matches your own lip color and not darker. I used to use liner and it did make my lipstick last longer using the fill in the full lip like you said. Still it would leave ‘ring around the lips’ look as lipstick/gloss & liner in middle of lips always wears off faster than liner on the edges. Matching your skin tone a la Smashbox’s way still does not work for me. I will end up with the ring around the lip look still. I don’t see a good answer other than to give up lipliners.

  • August 22, 2011

    HAH I love you for having the guts to post these bad example pics. :D I’ve seen MUCH worse lipliner crimes, so I think you were being nice about how bad they can get lol

  • August 22, 2011
    Kaye

    I LOVED this post !
    Seeing the “don’ts” is, for me, a good way to learn and I agree that showing how you corrected them into “dos” made it even better.
    I would love to see more tutorials like this. Even if it’s too time consuming to make them all as funny as this one- the concept is great so I hope you keep it up.
    Even parts of this that are basic things we should all know the reminder is much appreciated.
    Also- general comment- except if teaching something VERY difficult (and, since your readers are all going to be makeup junkies, I can’t think what that would be) I MUCH prefer text and photos to videos. Often I need to read things quickly (and QUIETLY!) and it’s so annoying to have to load a video; hear all the “filler” “babble”; wait to get to the part you actually want to hear etc
    . I have unsubscribed from several other beauty blogs that started doing almost every post as a video. I LOVE that you don’t do that. I can read it quietly. I can easily stop and pick up again in a few minutes. Nobody can overhear what I’m doing. I can save a photo for later reference. Sooo much better than video. So THANK YOU for that too!

    • August 22, 2011
      breeoxd

      yeah for few videos! I feel the same- can’t often use them! Great post, I need lots of help with liner lol

  • August 22, 2011
    Carmela

    Great guide, especially for ladies new to lipstick. :) I’m more of a gloss girl myself so these will definitely come in handy!

    I did pick up a trick from a makeup artist friend regarding wearing red/dark colored lipstick: To avoid getting lipstick on your teeth after you’ve applied your lipstick, stick a finger in your mouth, clamp on it with your lips then draw your finger out. The excess lipstick will transfer on to your finger and not your teeth. :)

    • August 23, 2011
      Nicole

      Came in to give this tip, glad someone else knows it because I was having trouble coming up with a description that didn’t sound slightly vulgar haha

      • August 23, 2011
        ReaderRita

        Yep, I started to write that the “finger pull” really works on another comment, and then heard the laughter of thousands of teenage boys in my head…so I changed it to “finger trick” instead, which could still be construed badly! LOL ;)

  • August 22, 2011
    aaminahs mom

    yes thanks so much….i being a woman of color see that eyeliner has been used for lip liner (black eyeliner)..IDK when that look came into season but i wish it never DID!

  • August 22, 2011

    I really like this ‘how not to’ post!
    Last weekend a saw a middleaged woman on the train with dark brown eyeshadow in a half cirkle above her eye, could have been done with a marker. I wondered if I should confront her nicely and explain how blending works. I chickened out ofcourse. So maybe you can do more of these posts and help all the people who need a little help looking the best they can.
    Inge (PolishSis)´s last post…SpaRitual – It’s Raining Men ( if the men are as gorgeous as this polish…then let it pour!!!! )My Profile

  • August 22, 2011

    I’m totally getting fired due to you. I just burst into laughter that first unblended liner is classically wrong.
    Kasey´s last post…Style Filed: 8/15-8/19My Profile

    • August 22, 2011

      Hi Kasey,

      LOL!! :D

  • August 22, 2011

    Ewwww! Hahaha great post, I dread the lip liner…my mom USE to do that but not anymore, however some of her mexican sisters still do! It’s so ugly I haven’t had the courage to tell them.
    Amanda´s last post…Comodynes Convenient Cosmetics: Self-Tanning Towelettes ReviewMy Profile

  • August 22, 2011

    Great tips – thanks! I was drinking my after-lunch coffee and as I scrolled down, the image of the clown lip lady came into my view and I literally said “HOLY CRAP!” out loud! *shudders*

    I am awake now! :P
    Megan´s last post…Time never waitsMy Profile

  • August 22, 2011

    A) Your eye make-up is STUNNING. I love the way you did your eyeliner. What I wouldn’t give for a steady hand….

    B) I LOVE the lipstick on teeth pictures. Hilarious!
    Senora H-B´s last post…21 Day Challenge–Day 7 (Mix Fancy and Casual)My Profile

  • August 22, 2011

    Ahahahahahhah this post is ironic, I think the worst thing about makeup addicts is to keep themselves too seriously, this is the reason I didn’t read them for a lot of time, this is the reason because my favorite blogs are no-serious at all. People, laugh more!!!!! This is just a hobby this is just a game to play, relax and go out with some lack sometimes, perfection doesn’t exist, it’s pretty boring and it’s a pain in the ass seeing people too maskered!
    Sorry for my language and for lecture, but I need to tell it sometimes, but claps for your post, great! ;D
    gnoma´s last post…Kiko – 335 blu inchiostroMy Profile

  • August 22, 2011
    Jelena

    This red looks gorgeous on you!!! Looove your blog, actually it is the only one I read on regular basis. Thank you!

  • August 22, 2011
    Beka

    I wish more make up artists knew this. I’ve had overdrawn lips done by professionals so many times. The worst has to be the photoshoot where I had to get the artist to redo my lips repeatedly as she made them smaller each time but they were still overdrawn until attempt number 4.

    Loving your look as well. Russian Red’s my absolute fave lipstick

  • August 22, 2011
    Josiane

    My boss wear her pale pink frosty lipstick with a raspberry liner, I can’t stand it!

  • August 22, 2011

    I think the worst offender for the “dark liner/lighter lipstick” crime is Kim Mathers, Eminem’s ex-wife.
    Chris´s last post…Tutorial: Glam Neutral Makeup for Tanned SkinMy Profile

    • August 22, 2011

      Hi Chris,

      Oh god you are sooooo right. Horrific.

  • August 22, 2011

    Yay! I loved this post so much! The lipstick on the teeth made me burst out laughing. This post is funny AND helpful. Thank you!
    Jessi´s last post…Chanel Peridot SwatchesMy Profile

  • August 22, 2011
    Jody Shank

    Seriously loved this post! Very good info, even tho u would hope most people know it already it never hurts hahaha. But no really,I loved this post. Hope to see more along the same lines :D

  • August 22, 2011

    Have you ever seen the ones who like to line their lips with black liner and then wear a light lipstick – particularly light pink and frosty – yep that’s right, wayyyyy heinous!

    and man… the pic of that lady… reminds me of that weird thing at the end of “House of 1000 Corpses” that chases his victim through Dr. Satan’s basement with a flamethrower :p

    • August 23, 2011
      Lesley

      OMG, that movie messed me up for like two days straight, particuarly the end in Dr. Satan’s basement!!!

  • August 22, 2011

    I have a thin upper lip and have been told by several ‘makeup’ artists to draw outside the line of my lips to make them look bigger. ??? This looks utterly ridiculous on me. Does that tip work for anyone? It ranks right up there with the Victoria Secret’s sales person telling me to go up a size on my bra since they don’t have double D’s. No. That doesn’t work.

    That lip woman is a reason why I don’t like clowns.

    Great post!!!
    Kimberly´s last post…Sunday’s A to Z about Me; Never UnpolishedMy Profile

  • August 22, 2011
    JenMei

    Love this post. A good advice is always appreciated. How about your gorgeous eye make up?

  • August 22, 2011

    This was a lot of fun to read/watch. Please do continue with such posts :)
    follytobewise´s last post…027 – FOTD: Ashy Plum LookMy Profile

  • August 22, 2011

    Bwahahaha!!! I absolutely love this post!!!

    Errors and corrections. Next up, how about the variations of drawn in eyebrows? From the sharpies to the permanent surprised or angry looks.

  • August 22, 2011
    Kristina

    This is hilarious! What a great idea for a post. The lipstick on teeth actually made me laugh out loud! BTW, i love the look you created on your eyes in these photos!!

  • August 22, 2011

    This is cute, I’d love to see more in this series. Also, that shade of red is super-flattering on you. =)
    Maggie´s last post…Estée Lauder Fuchsia Fever Lipstick.My Profile

  • August 22, 2011

    This is a great idea! It’s easier to learn what to do by seeing how it looks when it’s wrong. I still see the dark liner with the light lipstick and it’s awful! For lip liners I use Urban Decay Ozone which is clear and works well with keeping gloss on the lips. Target has Boots Line and Define Lip Pencils with a sharper at the end. I have the nude, red, and pink one. Great tip on how to avoid the ring around the mouth.
    Stephanye´s last post…LifeMy Profile

  • August 22, 2011

    what an awesome post, lol! your “overdrawn” lips look really hot upclose, is that wrong?

    i shudder and want to cry everytime i see someone with that ugly 90s look….sadly i get plenty at my job who come in with REALLY dated looks
    Vonnie (socialitedreams)´s last post…Celebrity Makeup Looks Recreated by Vonnie and ReadersMy Profile

  • August 22, 2011
    Never Enough Nails

    I like this post! Great idea! You could do how not to wear eyeliner, blush, etc. Very helpful!
    Never Enough Nails´s last post…Sally Hansen Summer NOTDMy Profile

  • August 22, 2011

    EPIC!

    so, I heard a scary rumour that that the darker lipliner trend was coming back. I hope not!
    MightyLambchop´s last post…Glam RockerMy Profile

  • August 22, 2011
    Ree

    Omg. The lipstick on teeth made me shudder. Eeech..

  • August 22, 2011
    Jen

    I LOVE, love, love this idea!
    When I have more time, I look forward to reading other posts.
    As a 20 something in the 80’s, I love to see what used to be a good idea for cosmetic looks then vs. what goes today. It’s amazing to me that you can still spot people rockin’ the looks of their youth! ;)

  • August 22, 2011
    Lucy

    I still see women with the ’80’s look of brown lip liner with the nude lip. Not even the lighter look of the Pamela Anderson look. Have even seen black liner with light lipstick. How horrific! When the Pam look was in I kept trying it at home and just couldn’t wear it. I finally got up the nerve and tried it a couple of times. I just felt too uncomfortable to wear again. My girlfriend siad I looked ridiculous and I knew it. I see a sales associate on TLC’s Say Yes To the Dress wear that dark liner w/nude lip. Her eyebrows are very exagerrated and heavy makeup. I wish she would lighten up the makeup and change her hair. She’d look so much younger. I have a thinner upper lip so I draw my top lip up a bit higher. Those red lips on that woman are pretty darn scary! Liked this post.

  • August 22, 2011
    Laura

    Here’s a tip when wearing dark lip colors. After applying color, place your index finger in your mouth, make a kissing shape and withdraw your finger. Any excess that could have stained your teeth, should now be on your finger and easily wiped away.

  • August 22, 2011

    Oh my GOSH I was so guilty of the darker liner/lighter lip back in the early nineties! I got over that quickly, thank goodness. Kelly this post is awesome – very helpful and really funny! Your lipstick on the teeth photo was hysterical and perfect. :) PS I have to agree with everyone, your eyeshadow looks fantastic. I wish I could pull off reds the way you do!
    Niki´s last post…Supplies: Revlon Quick Dry Top CoatMy Profile

  • August 23, 2011
    Sophie

    Well, I think the overdrawn example lady you’ve shown is neither overdrawn nor photoshoped. She’s got (massive!) surgery and a screaming red lipstick. Still gruesome though. Your overdrawn lips on the other hand don’t even seem wrong to me. I think they still look good. I’ve seen women wearing nude shades in the wrong colour practically all over their faces, which comes pretty good combined with a darker unblended lipliner. Yes, I’ve seen it all ;-)

  • August 23, 2011
    Mairyn

    Haha! Love the lipstick on the teeth photo. When I saw the heading I thought “Hmm, surely she wouldn’t deliberately do that” but then you did. I actually snorted.
    Definitely do more of these “how to’s in reverse” :)

  • August 23, 2011

    ahh no chola look? fine! haha <3
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  • August 23, 2011

    a few months ago I went in Naples (I live in Italy/tuscany) and there unblended lip liner is really common… but still terrible! A lot of italian video loggers have done a video tag “No, please, no” where they say what is really orrible to see and they all talk about this lipstick mistake XD
    A funny example
    http://www.youtube.com/watch?v=1lhLaNd2RGc
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  • August 23, 2011

    Great post! Your pics crack me up! XD
    I’d love to see more “how not-to”-s :)
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  • August 23, 2011

    Thanks for the great post! Loved it!
    Katherine´s last post…No Miss Quincy QuartzMy Profile

  • August 23, 2011
    Melody

    Good tips! Yeah I can’t believe that dark lipliner thing is still around. Do you mind me asking what your eye makeup was in these pictures? Your eyes look stunning!

    • August 23, 2011

      Hi Melody,

      That was in today’s post! Jesse’s Girl :)

  • August 23, 2011

    Hilarious!! I admit my fear of “ring around the mouth” often discourage me from wearing dark lipstick, I must learn to “re-apply” lipstick often!
    maisenzasmalto´s last post…NOTD: Chanel 507 TendresseMy Profile

  • August 23, 2011
    ReaderRita

    This post is hilarious AND informative- a match made in heaven!
    If you ever see a close up of Lucille Ball, she was the QUEEN of over-drawn lips, God love her… but it WAS the fashion then…
    You can really see it in this photo:
    http://tinyurl.com/3k5rvjq

  • August 23, 2011
    karmarat

    Just so you know, the “over drawn lip lady” is actually Amanda Lepore, a transgender model. http://en.wikipedia.org/wiki/Amanda_Lepore -And she is fabulous.

  • August 23, 2011
    Lesley

    This doesn’t really fit in 100% with this exact topic, but it’s something I’ve been dying for advice on: any suggestions on how to get good wear out of the OCC lip tars? I’ve heard such amazing things about them, but when I’ve tried wearing them (twice so far), they turned into a gigantic mess. I feel like I’m missing some vital trick or something.

    • August 24, 2011

      Hi Lesley,

      Lip Tar’s can be hard to work with and yes, they are messy even for me. You have to really use the SMALLEST amount you can imagine and they go a loooooong way. I just get a tiny amount squeezed onto a lip brush and apply that way. You cannot apply these from the tub because they will just get all over the place. A lip brush is definitely needed and I heard they made one now specifically for their Lip Tars.

  • August 23, 2011
    ReaderRita

    Oh, and BTW- how did you keep from cracking up while taking these pictures?! They are completely fabulous…and you look so …earnest…!
    SO much fun- great idea!

  • August 23, 2011

    This post was entertaining, lol. Pls go ahead with the others! :)
    Faz´s last post…Sweet ToothMy Profile

  • August 24, 2011
    Sandy

    What a great post! Good information and funny too because I have seen some women who do the very thing you should not do to your lips!

  • August 26, 2011

    I kinda love the spice lipliner look lol especially with viva glam V ;) I seriously think one day we well all wear that look again (i know what you think but think of all the once no-no’s we wear when a major brand declares it to be hot) just as long as the person wearing it feels pretty that’s all that matters, sometimes i really envy them for daring to show their favorite look without caring what others may think

  • August 27, 2011

    I’m with you about like… everything!
    Misato-san´s last post…Essence: like & not (feat Chiara XD) – parte 1/3 (viso, labbra e varie)My Profile

  • August 27, 2011

    I have some friends who still do the dark lip liner thing, maybe I’ll send them a link to this post as a hint!
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  • August 27, 2011
    Susan

    I have a friend that always had lipstick on her teeth. I always wondered how she got it in her mouth and on her teeth. I guess she didn’t blot. I like the way the lip liner is blended on the lips too. I usually do all my lips in the liner I chose then add a little gloss or lip shine. I don’t get so much mess nor do I get the clown look which I still see on department store clerks trying to sell makeup. You’d think they would know better. I liked your post.

  • September 7, 2011
    Audrey

    In my country theres a couple of luxury (kinda) duty free shop (where you can buy dior and chanel stuff for instance). One of them is called Marlène; usually this kind of ‘shop’ is to exude class, sophistication and stuff and. . .OMG it is so not the case actually LOL* Beetle Juice and and Cindy Sherman found their masters with our clampy lashes, overdrawned with black lips and stuff- girls !!!!! *HOOOORRIIIIBLLLLLLLE*

    Anway, thx for the post =)

  • September 16, 2011

    Lipstick on the teeth trick: After applying and blotting…open your mouth and stick your forefinger in it, close your mouth loosely (kind of like you’re blowing a candle out) around the finger and pull your finger out of your mouth. The key here is to make sure the only part of your lipstick covered lips that come into contact with your finger is the same part that might come into contact with your teeth – hence the “loosely.” There will be lipstick on your finger…not on your teeth!
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