I Tried Wearing Red Lipstick for a Week — and Only Lasted 4 Days

Amelia Tries to be one of those people who wears Red Lipstick.

You know how dogs in dog sweaters always look a little bit awkward? Like something is wrong?

That is how I feel the moment I apply lipstick: proper opaque lip lacquer, not the tinted sheer stuff that requires layers and layers to darken (although, shout-out to Chanel’s “Bonheur” Rouge Coco Shine, my ride or die, and Fresh Sugar Poppy Tinted Lip Treatment, which has SPF 15 in it). I mean bold opaque lipstick, like the kind Amal Clooney wears.

With lipstick on, I become immediately self-conscious, aware of my entire face from every angle and what my mouth looks like while I’m talking, looking, thinking, existing. It’s exhausting, so I avoid wearing it.

However, whenever I see other women in lipstick, they always look so pulled-together. Lipstick makes everyone who wears it appear fresh, full of life, fun and elegant — all the things I’d write in my online dating bio if I were still out there on the market. And for as much as I have a complex about lipstick and what I look like in it, I have an even harder time accepting defeat in this area. I know the benefits! I may be scared of lipstick personally, but I’m no optical stranger to lipstick’s magical ability to both finish, transform and jump-start outfits. When I’m mid-model-styling and can’t put my finger on what’s missing, lipstick is often the answer.

So why can’t it be for me?

I attempted to answer that very question and tried to be a casual lipstick wearer for a week.

Day 1: Impostor Syndrome

Day 1 was spent full of fear. I shouted at everyone who remotely turned their heads toward me: “I AM WEARING LIPSTICK FOR A STORY.” Most people replied, “Okay.” Some people said it looked nice and I should do it more often. Those people in the latter category are my new friends whether they want to be or not!

One of the main things for me with lipstick is that I’m already self-conscious as it is with my hair in a low bun situation. High pony? Fine. Braid? All the time. But a low slung, middle-parted bun makes me feel like an egg.

No offense to eggs.

Add the cherry lip in and it feels like like all the redness in my face is accentuated, like I should get back into Crest Whitestrips, like every acne scar is being highlighted. I am all for a celebration of so-called “imperfections,” (roll your eyes at that word; I just did) but it’s much scarier to celebrate them on yourself — especially with a neon sign pointing to the open vacancies of my not-yet-all-the-way-healed teen insecurities.

The rub here is that when considering red lips as part of an outfit, I much prefer how the whole thing looks with hair pulled back and no mascara. Adding foundation would have made me feel like I was wearing a full face of makeup, so I avoided, and thus spent the day wondering when I could head home to scrub my lips and let my hair go free.

I will say this: I loved the lipstick itself. The color was exactly what I’d imagine casual lipstick wearers “swipe on and go,” and it didn’t dry my lips out. (But still, I kept applying lip balm because I’m not used to the lipstick senstation.)

Day 2: Part of a Costume

Day 2 also happened to be Saturday night. I had a fashion-and-art-industry-folk dinner to attend (for Gucci) uptown, in Harlem, which meant that I wanted to have on something of a “Look” — and what you see above is far more look-y for me than usual — but I still wanted to feel like myself, keep the casual theme running and not resemble a parody of someone’s Wild Aunt Linda.

I actually wore a version of this outfit the night before (different audience, if you care), but without the lipstick (and different shoes and hair). In reviewing these pictures, the outfit you see here definitely looks more complete and far more interesting. The lipstick really did add something. Plus, the color’s great.

Self-conscious-wise, I ended up forgetting I was wearing lipstick until after the meal (it was pretty moisturizing). I also think was able to let go of some of my weirdness around a red lip because it felt like it was part of my Cool Costume that evening. Also, I added a TOUCH of mascara. That helped.

Day 3: Uneasy Like Monday Morning

My smile is a lie here. My face was still red from last night’s facial and the lipstick went to great lengths to accentuate it. I couldn’t decided if the color (a rushed mish-mosh of Chanel’s Rouge Allure Ink in 170 Euphorie and Yves Saint Laurent Vinyl Cream Lip Stain #411) went with this dress or what. Matching lip color to outfits, I have decided, is as hard for me as figuring out “what’s wrong” in an interior design puzzle. I get very close, but can’t ever quite put my finger on it, which drives me insane. I am in the business of aesthetics, for Christ’s sake!

But whatever. My hair was clean, so I wore it down for most of the day. That helped me feel more comfortable, especially during a meeting that I led where I spent the entire time acutely aware of my lip movements. I know my earlier visual was that of a dog in a sweater, but this felt far more like a Chihuahua wearing those balloon booties for the first time.

Day 4: “Add a Bold Lip”

When I started collecting answers for another story about how different women style their version of jeans and a tee-shirt, two said they’d add a red lip to elevate the outfit. See how easy it is for some people?? But in theory it made sense to me, so I tried the classic combination, but with a berry rather than a red. Red still feels too aggressive.

It was, for sure, the easiest of all the above, emotionally speaking. (All of the unprofessional makeup looks you see here took me about two seconds each, if we’re talking technical ease.) Plus, I had on the laziest version of my daily uniform: white tee, hair down, high-waist jeans. Without the mouth, I’d look like regular old me. With the lips, in this case, I felt more dressed up for some sort of an occasion. I loved the color and liked the overall effect. It even made me feel, dare I say…a little sexy.

In order to end on a high note, I decided to throw in the lipstick-covered towel after just four days. I figured I’d given it the old college try; I actually really liked how all the selfies came out; and besides, I’d accrued some helpful learnings along the way.

1) Lipstick really does make you appear more dressed up.
2) For me, constant lip balm application was key.
3) Excusing yourself to check your lipstick makes for an excellent conversation exit strategy.
4) It doesn’t appear on your teeth as easily as you’d think.
5) As with most things, no one is worrying about any of it as much as you are. To turn an internet meme into a beauty-positive affirmation, “Your lipstick looks great, sweetie.”

Lipstick mantra going forward, should I choose to apply: The dog in a sweater is all in your head.

Amelia Diamond

Amelia Diamond

Amelia Diamond is a writer, creative consultant, and Man Repeller alumnus living in New York City.

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