How To: Wear Any Lipstick Color (and Learn to Be a Little Braver)

For me, wearing red lipstick was a step toward overcoming my intense fears of failure. I felt like I had so many balls in the air at all times, and I had to be in control of all of them or I’d be found out. That whole “imposter syndrome” thing was alive and kicking in my world: I felt like I was never quite good enough, always chasing success but falling short, but that somehow, no one had noticed yet and I needed to fight tooth and nail to keep it that way. My need to be in control of my world had somehow extended to my makeup–all safe neutrals, nude lipsticks I didn’t even like, a routine that had become more rote than joyful. I couldn’t quite name my fear, but it was there, directing my every move. So I took one step to overcome it: I wore red lipstick. I know it seems small, but sometimes you have to find a manageable place to start. And you know what? Most people didn’t notice, and those who did offered compliments. But even more important, I loved it. I felt brave, strong, confident. I wanted to try more new things, to challenge myself further. This is where my makeup journey began, and what led me here today. It still strikes me as almost funny that the catalyst for change in my life was something as seemingly small as a red lipstick. It doesn’t sound brave. But it wasn’t so much about the lipstick. It was about choosing to do something  that I wanted to do but had been afraid to try, because it was out of my comfort zone. It was about opening myself up to the possibility of failure. It was about overcoming a fear I had barely even allowed myself to acknowledge. But that small act of bravery sparked more, bigger, more challenging acts. It was the beginning of a happier and more fulfilling life, driven by joy and not fear. If this sounds like you in any way, read on for my tips on trying new things (in this case, lipsticks, but you could extend its meaning as far as you like).

  1. Wear the lipstick for a significant amount of time. If you don’t read any more of this post, read this. This is the most important rule by far. We typically think we can’t pull off a shade because we put it on, decide “it doesn’t look like me,” and take it off immediately. Sound familiar? The problem with this is that of course it doesn’t look like you. Of course it’s unfamiliar. That’s the point of trying something new. You’re learning to see yourself differently. You have to give yourself time to do that. How you go about this will depend largely on the shade and your daily obligations. If you want to get used to a color that is not typically workplace appropriate, maybe one of the blue or metallic lipsticks that are very on trend right now, I’d recommend trying it on the weekend or a day you have off or are working from home. If the color seems appropriate for your workplace or appointments, then go right ahead and wear it all day! I’d recommend this if possible. Of the two, it really pushes you since you’re out in public, opening yourself to judgment–and often meeting none. This is key–people aren’t going to notice like you think they are. There usually aren’t packs of Mean Girls running around criticizing everyone’s clothing and makeup, and if there are, they have less of an impact on your life than they did in middle school. No matter which option you choose, though, I do recommend wearing at least some other makeup with the lipstick–maybe a full face, or maybe just some mascara, so that your lips aren’t drawing all of the attention and your face appears more balanced, closer to how it would look on a regular basis. In scientific terms, control for the variable (the lipstick). The other key is this: Look in the mirror as often as possible. The best way to get used to seeing yourself in a new light is to actually see yourself. The more you see yourself wearing that lipstick, the more “normal” it will look. At the end of the day, evaluate: Did you like wearing the lipstick? Did you feel confident? Did you feel exhilarated when you caught a glimpse of yourself in the mirror? Did you start to get used to the color? If the answer to many of these questions is no, then maybe try a new finish or tone of the same color. Don’t write off all reds, for example, because one didn’t work for you. We have a tendency to overgeneralize when we’re scared; instead, if it’s something you want to do, keep trying. Read on for more tips on choosing the right shade.
  2. Pay attention to the finish of the lipstick. I am fully convinced that when we think a color doesn’t work for us, the culprit is really the finish. Lipstick finishes range from the most matte, dry-as-a-bone-looking liquid lipsticks to the shiniest of glosses. Your primary options tend to be, from most matte to most sheer: Liquid lipsticks, which are typically the dryest, flattest, mattest formula and typically look like a gloss with a doe-foot applicator; matte lipsticks, which are tube-lipsticks that have a matte finish, though the degree of “matte-ness” varies from one brand to the next; cream lipsticks, which is the formula you typically associate with a tube of lipstick, your usual moisturizing, somewhat shiny finish; pearl or metallic lipsticks, which have some degree of shimmer or glitter in them; sheer lipsticks, which are like creams but are less opaque; and finally lip glosses, which are wetter, usually sheer but not always, and typically very shiny. As a general rule, if you’re trying to get used to new colors, I recommend sticking with the matte-to-cream end of the spectrum for darker lipsticks, and the cream-to-gloss end of the spectrum for paler shades. There are two reasons for this. First, this tends to be the most wearable on most skin tones, since a matte finish help a dark color recede from focus a bit whereas glossier shades look brighter and fresher, but are also more noticeable. A glossy dark lipstick might draw more attention to a new color. Maybe you’ll want to try this down the road, but when you’re starting out, mattes can be a bit easier. Second, matte lipsticks tend to stay in place better than glosses, so if want to be confident that your dark lipstick isn’t a mess or bleeding outside your lip line, try a matte formula. This is not to say that you can never wear a glossy red, but that you need to decide your comfort level with that formula and if a shiny red is appropriate for any given situation. A date night? Absolutely. A faculty meeting? Maybe not.
  3. Pay attention to your undertones, and try to match those to the undertones of the lipstick. This is not as difficult as it sounds. If you look better in cooler colors, you probably have pink undertones and would look better in cooler lipsticks. These are often described as having bluer undertones. If you look better in warmer colors, you typically have yellow or olive undertones, and should look for lipsticks that have more orange undertones. I still believe, though, that again, the finish of the lip product is more important than the undertones. I have a warm skin tone, but today I’m typing this post wearing the Colourpop Lippie Stix in Whip, which is a sheer blue-toned purple-pink. The emphasis here is on “sheer”–because it is not as strong as a cream or matte, I can pull off a color that doesn’t, by the book, fit my skin tone. I find this is true for pale colors as well. I look better in pale pink lip glosses than a pale pink matte lipstick, as the sheerer formula of the gloss just looks a but more natural and is a bit less opaque than the dryer matte formula. Regardless of how pale or deep your skin tone is, in general remember that if you’re wearing a shade that is lighter than your natural lip color, it will probably look better, at least as you’re in this experimental stage, in a gloss or sheer, regardless of its undertone. But if you think you can’t pull off red or pink lipsticks, do think about undertones. If you’ve already found a finish you like but the color still isn’t working for you, this might be the issue.

And in the end, always remember that failure is an important part of life. I don’t say that to be flippant or cliched. What I mean is that as adults, we often find that our middle-school insecurities hang around a lot longer than we realize, and can prevent us from trying new things for fear of failing or not fitting in, for fear of being noticed or criticized. In middle school, we thought that wearing the wrong outfit one day would brand us as unpopular for life. And that may have been the case then–kids can be mean, and they haven’t developed any sort of long-term thinking or sense of consequences. Empathy often isn’t part of the middle school repertoire. But as adults, we’ve all developed a bit more perspective. We’ve experienced joy and heartache beyond what we could have imagined in middle school, and we can be more forward-thinking than we once were. We recognize that while every day matters and we should live it to the fullest, we also recognize that a day is just one day among many, and all are full of opportunities.

If you want to read more about challenging yourself to try out new colors and techniques that you might have thought were unwearable or inaccessible to you, check out my One Brave Thing series. Here, I’ll talk specifically about certain trends, such as deep lip colors for fall, bright eyeshadows, contouring, strobing, etc., and suggest how you might adapt these trends to find what best fits you. Because if it doesn’t, what’s the point? Makeup should never be about someone else. It should serve to make you feel more like you, more comfortable in your own skin, every day. And it should serve a process of growth. If it’s not doing those things, it’s time to try something new. Do One Brave Thing.


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