Red Lipstick Challenge: Conquering Fears and Perfecting the Art of Red Lips

Red Lipstick

Red lipstick: Depending on who you ask, it can be everything from iconic to trashy. For every person who adores red lipstick, there’s ten who abhor it. I first started thinking about this when I polled my friends, and asked them if they thought I should wear red lipstick to my friend Molly’s wedding. Responses ranged from, “You’ll look like a teenager trying to act older,” to “It’s too whorish,” to “You’re going to get too much attention for it.” None of these comments really had anything to do with me so much so as the strong feelings people have for both for and against red lips.

The truth is, I’ve always loved red lips, even more so now that I’m in my twenties. It just feels quintessentially classy in a perfect Marilyn Monroe way with a bite of Dita Von Teese. Speaking of Dita, she is just my absolute style icon, and after reading her interview over at Into the Gloss, I came to the realization that makeup takes time and practice.  (Did you know she has a whole vanity drawer just for red lipstick?) That’s true for everything from a simple smokey eye to the perfect red lip. No one figures it out overnight or on the first time. While in college, I bought a single Wet ‘n’ Wild black shadow and attempted a smokey eye. It did not end well. However, years later, I know it takes more than one color, more than once brush. Plus a lot of patience and willingness to get it wrong.

After reading that interview, I was brought back to my love of red lipstick. It takes a fair amount of bravery to put it on and even more patience to apply it right. I’ve always wanted to be one of those women who looks like they’ve effortlessly thrown on red lipstick before heading out the door. However, you can’t have that if you don’t practice. Without practice, it will always be hard and haphazard. Which brings me to the point of this post: For the next month, I’ll be wearing red lipstick for five out of seven days of the week. Sound familiar? That’s because I did the same thing with high heels back in August and September. And it all starts tomorrow.

I often hide in the safety of a nude gloss or pink lipstick. Part of me is sick of hiding and the other part just really wants to perfect red lipstick. And the other part of is terrified, which is why I’m posting this here, because if it’s on the blog, then it has to happen, right? Right!

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  • Arash Mazinani

    I love these little challenges you keep setting yourself. I’m a massive fan of the heel challenge and your observations at the end of it all.

    I love that you’re trying new things and pushing yourself. I personally think lipstick looks great on women as long as it’s been applied neatly. My mum has always worked with make up and some people are just gifted and have a natural instinct to apply it and it look amazing. Others like you said it takes time to get better at it.

    Good luck with your new challenge, I look forward to see your progress.

    • Courtney

      Thanks Arash! I think I’ve always been someone who sets up little challenges, and I think having a blog only makes it more exciting!

      Your mom is a lucky lady! For most women I think it takes some time to figure out how to apply makeup so it looks good. A lot of times, it’s just understanding your own facial structure. So much goes into it you wouldn’t usually think of!

      Thanks for all the support!

  • Cassie

    I think it’s really interesting how strong a reaction colouring your lips can get. I find this kind of social signalling fascinating. I wonder what it is about red – on your lips, on your nails, on your cheeks – in particular that seem to scream “WHORE” to such a large chunk of people?

    • Courtney

      It’s very interesting the reaction people have to it! The comment was made more in context of the idea of red lipstick–multiple people I know called it whorish or “too much,” but didn’t necessarily say it to me while I was wearing it. It was interesting to hear the strong opinions, though!

      • Cassie

        It always tickles me when people describe sterotypical “whorish” things, because in five years as a receptionist in the sex industry I met maybe two working girls who ever wore bright red lipstick at work. It’s far too fiddly to be practical.
        But as you say, it is fascinating how strongly people react to red on a woman. I wrote a big long piece about it over on my blog when reviewing OPI’s I’m Not Really A Waitress, if you’re interested in taking a look some time.

  • Laura S

    I LOVED that Dita Von Teese article!
    But, seriously, I love red lipstick SO MUCH, it’s kind of my personal makeup trademark. A part of me is worried now that I don’t do it right because I pretty much swipe on some lip balm, swipe on red lipstick, and head out the door? Well it looks good, so I’m not going to worry about that, haha. Though, if I know I’m going somewhere where I’ll be eating, drinking out of a clear glass, or not able to reapply lipstick (or whever I have time, basically, which unfortunately doesn’t include the morning on my way to school), I’ll swipe on lip balm and a layer of lippy, close my lips/bite (without teeth) a kleenex, swipe on one more layer of lipstick, do the kleenex-biting again, then taking a kleenex, placing it directly on your lips, and placing some powder or blush on top of the kleenex to set it. Then, depending on how strong I want to the lipstick, I’ll either just apply one more layer of lipbalm, or also another layer of lipstick.
    After that long tip, all to say, I hope it helps?
    But aaaaaw, why would people think you look whoreish? If you’re not wearing a corset and fishnet tights and layers upon layers of black eyeliner and too much blush, then, alright, I guess you might remind people of a whore. (I still think people you should look however you want to in regards to makeup and clothing, though, so even if you did do that, kudos to you!)
    But I always think of classy and confident when I think of red lipstick, so next time you should totally wear red lippy with a black dress (which was so cute, from what I could tell on instagram!)
    It’s SO great that you’re taking on this challenge! I think it’ll be fun ;).
    – Laura

    • Laura S

      And wow, sorry about all those typos, my keyboard has been acting sticky today and I’m half-asleep with stress. (Which made no sense, but we’ll pretend it does.)

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  • Kara @ Bostonista

    I have a feeling that it will look so gorgeous and NOTHING like any of those comments! It is funny that people have so many negative connotations with red lips when its really just a classic look. Where did these ideas come from? Super old movies when the female vilans wore red lips?


    PS: Please enter my giveaway with Rent the Runway!!!! xo

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  • Casee Marie

    Yesss! I’m so glad you’re challenging yourself with red lipstick and I can’t wait to see how it goes. I’m definitely surprised that it gets such strong criticism – I wear it just about every day (pretty much unless it clashes with my outfit) so hopefully I don’t evoke those kinds of reactions from people. But to each their own, right? I love Dita, she’s a huge inspiration for me too, and I completely agree with your sentiment about make-up taking time and practice. I think it’s also vitally important for people to really study their own faces and get to know their natural contours. As a random example, my eyes are deep-set and I have natural shadowing above the crease, but I’ve always put dark shadow on or under the crease like I’ve seen so many others do. So I was essentially trying to move the contours of my eyes. But recently I decided to try to work with what’s naturally there, using a loose brush to put darker shadow above my crease, and the effect really made my eyes look bigger. All these years, I never tried that movement. Make-up is a continual learning process, that’s for sure. (:

  • Rachael @ Style Every Day

    I love the idea of making yourself try it out multiple times a week! Can’t wait to see what it looks like!

    • Courtney

      I’m going to aim to take pictures every day so hopefully I’ll have a really nice post at this time next month!

  • Veshoevius

    Whoa – those are some pretty severe reactions to a make up classic! I love red lipstick – have always worn it and always will. I tend not to wear bright shades to work though (but that goes with blusher and eyeshadow too)

    Will be interesting to see how people react to you over the five days!

    • Courtney

      I was as shocked as you are!

      I work in IT, which means I can pretty much wear anything I want as far as makeup goes. Most of the guys I work with wear jeans and a t-shirt everyday. Most of the women are somewhere in between casual and professional wear. Luckily for me, there’s lots of room to do whatever I want.

  • Heather

    I wear red lipstick all the time. If not red than burgundy, fuchsia, or coral. The trick is to go natural with the eyes. Try putting on the lipstick first, then add blush and eyeshadow. I find with red lips all I need is my BB cream, a bit of blush and mascara. When I was younger I wouldn’t bother with the blush. All this talk about red lipstick being whorish is just weird. It’s classic and sophisticated. Period.

    • Courtney

      I’m with you on that one! You’d be so shocked at how strongly many people hate red lipstick! In fairness, I did ask their opinion, so it’s not like I got unsolicited, “You’re a whore!” for wearing red lipstick.

      I learned that trick too last weekend! If you go strong with lipstick, do it first then fill in everything else.