How Red Lipstick Taught Me to Be Brave


The Red Lipstick Challenge has ended after over a month of wearing red lipstick almost every day. What started off as a fun challenge turned into an enlightening experience of bravery, boldness and self confidence. I didn’t expect that from a simple tube of red lipstick. In fact, I was skeptical if this challenge would change me at all.

In the beginning of the challenge, I was afraid to go out in public with my red lips. There was something unnerving about people staring at me, whether they did it out of judgement or inherent curiosity. But this isn’t a story about strangers, it’s a story about me. I went from being doubting myself every time I wore red lipstick to embracing it entirely. It became apart of who I was, almost like a character trait. I wore it when I was so happy, when I was terribly sad, when I was sick and once accidentally when I was going to the gym. I wore it on Thanksgiving and on Christmas and most days in between.

The most shocking part was the amount of conversations it sparked, both online and off. One night, I ran into a girl who told me she could never wear red lipstick. I told her about my project and by the end of the conversation, I was making recommendations about shades I thought she’d like. Several friends of mine went out and bought their first tubes of red lipstick. We started talking about what role makeup played in our lives and how it impacted our relationships. (By the way, David has come around somewhat to red lipstick.) The conversations I was able to have with women, some strangers and some my best friends, made this whole experience worth it.

Something odd happened the other day. It had been about a week or so since I donned my red lips. I sat at my vanity, eyes running over all my lipstick options. I picked up my favorite, NYX’s Pure Red, and got a rush of excitement. All over, I was scared. What would people think? Could I wear this to work? I was scared, but when I put it on, I got that burst of confidence I had remembered so well.

Will I continue to wear red lipstick? Without a doubt, though I have to admit, I am happy to take a break, at least for a little bit. I know changing my lip color may seem trivial, like it shouldn’t matter. Who cares what color my lips are? At the end of the day, though, I care and that’s all that matters.

Practical Tips for Wearing Red Lipstick

Here are just a few of my tips for wearing red lipstick.

  • Blot. Yes, this is number one because you absolutely need to do it. Without this, you risk getting lipstick on your teeth, on your face and clumping. Blot with a tissue and try to avoid using toilet paper. Do not use paper as this takes off most of the color.
  • Get a lip brush. For my first application, I always use a lip brush to define the shape of my lips. With a brush, you have increased control over your application.
  • Carry your lipstick, lip brush and mirror. Red lips are a commitment. You will need these things to maintain your color throughout the day.
  • Red lipstick gets everywhere. So carry your concealer and stain remover pen, too. If you accidentally touch your lips and then your nose, you can easily cover it with concealer. If you get it on your clothes, don’t fret. It will come out.
  • Use balm when you give up. Let’s face it, some days you will want to give up. When you lipstick starts to fade, use a balm to even the color out. It happens.
  • Nui

    I love lipstick. I would love to wear it everyday but I can’t. Anyway, I wearing red lipstick whenever I feel sad. I don’t know why.

    • Courtney

      I do that, too, sometimes! It brightens up a sad day.

  • Mango

    This is exactly the challenge I will be doing for next month, I thought this goal was original (apparently not) lol. Hearing you experience gives me some hope that maybe people won’t shun me at first sight. I took this challenge on because I was/am so tired of putting red lippies on, only to wipe them off before I’m out the door. Mmm never thought about messy red lips – looks like I’ll need to do more research :/. It’s so funny because seeing all your red lipped photos I can’t imagine why you would fear it – it looks great on you! I guess that’s just how this red lip phobia attacks. Anyway, thank you for showing me it can be done !! πŸ˜€ !!

  • Jennifer Stables

    I usually do pretty dramatic eye makeup but after have twins I never have the time to apply it. I just didn’t wear makeup for the first year. I missed it so decided to give lipstick a try. I bought a bunch of shades and tried them all over a course of a few days. I fell in love with a lip liner lipstick combo in one tube called Vermillion. I couldn’t bring myself to wear it out. I posted a picture on Facebook saying wish I was brave enough to wear this out the door. Most of my female friends told me to go for it and I did. Wore out that day to a family dinner. Felt good about it but definitely had on my mind the whole time. My only problem is I don’t go anywhere special mainly grocery shopping and the usual Sunday family dinner. Is grocery shopping the place to wear red lipstick? I also just wear it with a cute top and jeans.

    • Courtney

      I think once you get used to it, it kind of fades into the background. The second I started wearing red lipstick, I definitely felt the stares of strangers, but after awhile, I noticed less and it mattered less. I personally think you should wear what you feel best in, and who cares what everyone else thinks? After all, it’s just lipstick!

      I indeed wear my red lipstick to the grocery store. And to work. And everywhere else except the gym. Once you take the leap, it gets a lot less scary!

      What brand is Vemillion?

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  • Rofique Hussain

    I wear red lipstick almost all the time πŸ˜€ i guess it gives me
    some confidence but mostly it’s just some kind of habit i
    <3 the post xD

  • Elle

    Hmm…I’ll check it out and see what I can find.

  • Elle

    I recently started wearing red lips a lot. I actually started with a gloss, but I absolutely fell in love with it, and I really like matte lips, so I bit the bullet and bought my first red lipstick that wasn’t for the stage! (I used to dance and do theatre, so wearing crazy makeup isn’t foreign to me, but doing so in everyday settings is still pretty new). I wore my red lipstick for the first time today, and I LOVE IT! I’ve gotten multiple compliments on it and honestly, I feel GREAT! It’s like an instant confidence booster, although, at the same time, it is like putting yourself out there — and REALLY out there!! But you know what? That’s okay. It’s like taking a risk that in the end is totally worth it!!

    • Courtney

      What lipstick did you end up buying?

      You’re so right–red lips definitely make you stand up. I’m always so surprised MORE people don’t wear it, both at night and during the day. Maybe it’s just Boston, because I”m sure people in NYC wear red lips more frequently, though that’s just a guess.

      • Elle

        I bought Nars Velvet Matte lip pencil in Cruella and Dragon Girl. I love them both! I’ll be adding to my collection soon though…I want all sorts of reds, pinks and purples (I just bought a purple one last night, can’t remember the name off the top of my head though). Lips are so much fun!! I’ve in the past just gone with high gloss, but got into matte a few months ago…so I put the two together — bold but matte=red, LOL.

        Yeah, I too am surprised more people don’t wear it. Oh well…makes us stand out even more and show our uniqueness!!

        • Courtney

          My little sister got me the Nars Cruella pencil for Christmas! I just wore it on Tuesday. It’s a bit too blue-undertoned for me, but I do like it. I prefer red-orange lipsticks, BUT I have so many that I have to branch out.

          I prefer matte lipsticks, too. Nyx Cosmetics has AMAZING matte lipsticks for about $5 if you want to save some money. I have about five and I LOVE them. I have a review planned soon.

          • Elle

            You should try Dragon Girl. It’s definitely more orangey than Cruella.

            I don’t know why I prefer matte lipsticks…it’s not like I prefer matte lips overall…I’ll wear high shine gloss like nobody’s business…but if I do a lipstick, it’s matte 99% of the time.

            Where can you buy Nyx? I always read about it, but have never seen it.

            • Courtney

              I’ll check out Dragon Girl for sure!

              Nyx you can find at Ulta or online. Random places carry their eyeshadows (Urban Outfitters, Nordstrom Rack), but the best place I know to go in person is Ulta.

              • Elle

                Hmm…I’ll have to look online. There’s not an Ulta anywhere near me.

                • Courtney

                  Here’s their store locator:

                  You might want to call again, though, because a lot of times they don’t carry the lipsticks.

                  • Elle

                    I’ve looked at the store locator for Ulta…the nearest one to me is about 15 miles away, and I don’t have a car…so online is pretty much my only option when it comes to Ulta. But apparently PacSun sells Nyx…and there’s one in the mall really near me…

                    • Courtney

                      Not entirely sure they carry the matte lipsticks is the only thing, from what I can gather online. If you order on, you should be able to return it if it doesn’t work out. You can also shop or ( same company, not sure which one carries Nyx. One or the other.)

      • Yarii

        I love red lipstick! But i live in NY and in certain areas people tend to stare at you because you stand out:/.. I remember the first time I wore a dark red lipstick I felt horrible because I would be constantly looked at especially by girls my age or older :/. But after wearing it for a while, I’ve gotten used to it and I love both bright and dark red lipsticks (I use Nars red lizard and MAC media) ^-^. You’re right tho, in the city everyone tends to step out of their comfort Zone which is great:)!

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  • Marisa Anderson

    Your pics are wonderful. I too wear red lipstick for those days when I want to feel extra confident. There is just something about red lipstick that makes a person just feel so sassy, confident and bold!

    • Courtney

      Thanks Marisa! And I couldn’t agree more! Some days when I just need that extra “something,” I often go for red lipstick.

  • mimo

    This is a fab blog post! Red really suits you! Would you typically wear yours to work?

    After years of wanting to emulate Gwen Stefani, I bought my first red lippy this week.

    It’s a No. 7 (UK brand) lip paint that comes with a tube of clear gloss. It’s. Very. Very. Red. I put it on, expecting to look like a clown and was surprised to see that it looked pretty cool. I also discovered I have small, pouty lips. I’ve always neglected them or just used a bit of vaseline or my subtle nude lippy that rubs of very quickly. I decided to wear it to work yesterday. I felt excited as I put it on and I had a spring in my step on the way to the tube station. I got a lot of looks on underground, but I didn’t feel like this was because I looked awful. At work, a few colleagues said that it really suited me. BUT… I noticed a number of other co-workers looking at me strangely, or looking at me, then suddenly looking embarrassed and looking away. I started to panic that I looked either a bit trashy for work or like a teenager who’d just raided mum’s make up box :(

    I’m too afraid to wear it to work again!

    • Courtney

      I do wear mine to work! I work in IT, so the dress code is a bit lax, shall we say, so I can get away with wearing pretty much whatever I’d like.

      I had that SAME reaction when I first wore it to work. I tweeted the same thought and someone asked if maybe it was just ME who was scared. The truth is, red lipstick will make some people stare, but you just have to get past that. Mostly I think it’s because very few women wear bold lipstick during the day, if at all. It makes you stand out for sure, but you just have to get comfortable doing it.

      My advice for you, based on my experience, is give it another go!

  • Jasmine

    I’m still working up to confidently wear bold colors. I have such thin lips I think I look funny!

    • Courtney

      You probably have to get used to it! When I first started wearing red, I was convinced I looked like a clown. Now I love it.

  • Arianna @ Arianna’s Random Thoughts

    Love this post! Way to go :) Congrats on completing the challenge. I have recently got the courage to wear red lipstick but I wear it once and while – like to mix up the colours. I think I may follow your challenge though – it sounds like a great idea. Thanks for inspiring me!

    • Courtney

      I’m so glad you were inspired! Please come back (or tweet me–@msfemminista) if you end up doing a challenge of your own!

  • Vanessa, Take only Memories

    What a great challange! I am one of those people who can’t wear red lipstick. But unlike the girl you met there is very little that could change my mind. I really do look awful with it :(

    • Courtney

      Have you tried different undertones? I look bad in red lipstick with blue undertones, but I ADORE red lipstick with orange yellow tones. Might be worth giving a go!

      • Vanessa, Take only Memories

        Hmm…interesting. I hadn’t thought of that. But I don’t really ever wear any color lipstick. I always end up looking odd..

        • Courtney

          Maybe try applying with a lip brush instead of directly onto your lips from the tube. That way you can control how much you apply. I find direct application to be a bit harsh sometimes.

          • Vanessa, Take only Memories

            Yeah, I’ve tried that…but thanks so much :)

  • Kara @ Bostonista

    Congratulations on completing the challenge! I love red lipstick but a friend made a comment one time when I wore it years ago and I’ve been afraid to wear it ever since except at blogger or fashion events. Isn’t that terrible? Proud of you for wearing it loud and proud!


    • Courtney

      Thanks Kara! I think you should give it another go! Lots of my friends (even my husband at times) don’t like it, but I just say, “Whatever!” Haha. Let me know if you give it a go :)

  • Jamillah

    that’s pretty awesome, courtney. i haven’t found my red lipstick yet! b/c i was tackling all the shades of pink i wanted (finito, post coming soon) but when i first started wearing lipstick i totally felt the same way a little self conscious! i’m glad i was not the only one! now i totally feel a dash sexier when i put it on and it makes me really happy. love your tips! blotting for realsies super important and yes it is a commitment!

    • Courtney

      Blotting is uber important!

      I think it’s all about finding a color that works for you. May not be red, but might be pink :)

  • Ylenia

    lovely challenge! and you look amazing in that red lipstick.
    I love wearing it either but I do not like to be at the center of attention and when I wear red, it looks to me like every men is looking at me!!!

    Love, Ylenia from Longuette

  • Sheila

    I love that you committed to doing this for a full month! What a great challenge to yourself! I wear red lipstick here and there, and I’m always amazed at the reactions people have to it.

    You look beautiful in red!

    • Courtney

      Thanks’ Shelia! The whole project was quite eye opening.

  • Bella Q, The Citizen Rosebud

    I will always love red lipstick!

    • Courtney

      Same here, girlie!

  • Chiara

    I’d like to be brave enought to wear red lipstick at work. Besides, it’d fade after 1 hour!
    Liked this post so much I included it in my Sunday list.

    • Courtney

      You can always start off with a gloss! Also, you’re right–it does fade but if you do a first good application, it should last a few hours without needing a touch up. However, you do need to touch up!

      Thanks for including me:)

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  • Dawn

    What an amazing challenge! I used to wear red lipstick all the time during the summer but I haven’t worn any for a few months now. I’m going to challenge myself to wear red lipstick during the weekend now.

    • Courtney

      I love that, Dawn! I think it’s great to try. Especially in winter when everything feel so desolate, at least here in Boston.

  • Veshoevius

    What an experiment this has been and fascinating round up here – I was interested to read how you feel it has impacted your self confidence in a positive way and even inspired some of your friend to experiment with red lipstick too!
    Happy New Year!

    • Courtney

      Everyone should own at least ONE red lipstick, I think!

      Hope you’re doing well girly :)

  • Cassie

    As I saidon Twitter, I think this is a fantastic challenge. I love to see people really pushing themselves, you know? I’ve done a lot of things in the name of pushing myself, but I think I would be just too self conscious to pull this challenge off. Super impressed!

    • Courtney

      Maybe start off trying something like this once a week instead of every day. For me, I’ve always been an “all or nothing” person, so I either have to do something extreme or not do it at all.

  • Tashia

    I have always cowered away from red lipstick, trying a pixie cut or wearing false eyelashes on nonhalloween occasions for fear of the extra attention. It takes a lot of confidence to be that bold and I admire you for it:)

    • Courtney

      I always go all out on Halloween too, but I recently started wearing falsies just because. Because? Why not! At the end of the day, we should all do whatever it takes to just feel like ourselves, and if that means falsies or red lipstick–I say go for it.

  • Heather

    What a great post. Via our conversation on twitter I must say your collage is perfect and just what you needed for the post header. As for red lipstick, I wear it a lot, day and night. I also wear hot pink and fuchsia and coral. It never seems like too much. Am I weird? I might have to take your challenge and see what it’s like wearing red EVERY day.

    • Courtney

      You should go for it! Please share if you do!

      The collage came together nicely, I think. I was a bit worried, but I think since it’s mostly small images of me and my red lips, it’s OK. And also, I think there’s something to be said about doing a habit even when you are sick, sad, etc. I look at those photos and remember what I was going through on that day or what I was thinking. And they are all tied together by the lipstick.

      • Heather Fonseca

        I’m started a red lipstick challenge of my own! I’ll be putting on some red lipstick every morning and I’ll tweet a photo too. I’ll probably post about it too eventually. Thanks for the inspiration!

        • Courtney

          I’ll be sure to check it out on Twitter!

  • Lydia

    My dad likes to tell me that I look like a “lady of the night” when I wear red lipstick, but I’ve learned not to listen to him as much anymore πŸ˜‰ I think the best part of red lipstick is how you just have to own it, and I agree, it really does help you engage your self-confidence. I used to wear LOreal’s great red that had Evangeline Lilly’s signature on the side, but I’m nervous about what’s in it and stick to my NARS Red Square, but don’t like red oranges in the winter, so basically what I’m saying is I’m on the hunt for a bluer- pure red for winter :)

    • Courtney

      I definitely got that a lot too! What I forgot to include was when I was in Columbia, I walked into the grocery store and I’m 99% sure someone looked at me and said, “Oh lord have mercy!” LOL

      This whole challenge really needs to be its own blog because I also just thought of how at first I didn’t think undertone mattered AT ALL. That is until I got absolutely addicted to red/orange red lipsticks. I don’t much like red/blue ones. I’m pretty pale always so red/orange works.

    • Heather Fonseca

      Lydia, if you’re looking for a nice blue-red lipstick that doesn’t cost a fortune check out Maybelline’s “Red Revival”. It’s a beautiful color!