I Wore 12 Days of Bold Lipstick Shades Because I'm Afraid of Lipstick

For the first day of the challenge, I definitely eased myself in by applying a matte red lip that didn't seem too intimidating in the tube. Because it was a flat formula, it was a bit drying. It rubbed off pretty easily, which I noticed when I took my first sip of morning coffee and saw a pale red lip print on my cup (I fear I also ate tons of it during lunch).

However, I felt comfortable in this all day and even got a few compliments on it (though I'm not sure if they were "OMG cute color!" comments or "OMG you're wearing lipstick whaaat?!" comments), which was encouraging and geared me up for day two.

Product: Dior State of Gold Holiday Collection Lipstick in Fascinate ($38)

I woke up feeling excited yet apprehensive. This Kat Von D lipstick is brighter than anything I'd ever worn, so I was a little worried about how it was going to go over. It's another matte fomula — though, again, it rubbed off pretty easily (I was asked to prove it by lightly touching my finger to my lip way after applying, and my finger came back full of color).

Since I wasn't prepared to not be able to touch my face freely, I found lipstick all over my hand and on my chin when I went to check on my pout in the mirror. Still, the color was beautiful. It made me feel fierce walking down the cold(ish) New York City streets, and the compliments I was receiving — no, I did not get my teeth whitened, but thank you for asking! — as a result of this bright red hue made it easier to deal with.

Product: Kat Von D Studded Kiss Lipstick in Bachelorette ($21)

I FELT LIKE A BOSS IN THIS LIPSTICK. The texture was awesome — hydrating yet long-lasting — and I couldn't stop taking selfies all day. It didn't rub off as easily as the others I'd tried so far, and I completely forgot to care about it while I was eating. This cherry shade is going to be one that I rewear often. (Also, holy packaging, Batman!)

Product: Burberry Kisses Lipstick in Military Red ($33)

The NYX lipstick went on like a dream — it was so smooth to apply — but for the first time since starting the challenge, I felt a little insecure. While the metallic copper color definitely looked better on my lips than I thought it would, I decided that a metallic shade wasn't giving me the same ego boost that the solid reds had given me thus far. Throughout the day I felt self-conscious and not myself, constantly checking the mirror to see what I looked like. That being said, it stayed on all day, and unlike the others, it didn't come off while I was eating. That fact alone makes me want to try a more "me" lip product from this line.

Product: NYX Wicked Lippie in Wrath ($6)

While the gold tube was gorgeous and the slight marshmallow scent enticing, as soon as I put the matte nude color on my lips, I missed my former vibrant shades. I felt a bit too washed out in the nude tone, and to be honest, I didn't leave this one on long enough to really evaluate it much further. However, it seems like its staying power would have been fantastic, and I loved the formula, so I may have to give this one another whirl once I'm sunkissed next Summer.

Product: Charlotte Tillbury K.I.S.S.I.N.G. Lipstick in Nude ($32)

A week before this little project, I would have said "hell to the no" at this color, but man, I loved it. This lipstick is actually sold in a duo, called Ice Queen Story — one product is Ice Queen, a straight-up white color, and the other is Wine Sinner, the dark maroon.

When I first applied it in the morning, I used the creamy white shade underneath the dark crimson. Throughout the day I chose to only reapply Wine Sinner and was definitely more into that result. The formula was buttery, and I found that it stayed on my lips all day with very minor smudging when I touched my lip area (which was now all day, every day).

Product: Lipstick Queen Ice Queen Lipstick Duo (Wine Sinner) ($45)

Today I was told by one of our beauty editors, "THIS is your color, we found it," and I basically couldn't fit my head through the door for the rest of the day due to the implied compliment. That being said, though it was an amazing brick-red color and went on super smoothly, it came off just as easily (note the cute little smudge on my front tooth). I must have also kept touching it, because I ended up with dark red smudges all over my (white) keyboard, (white) shirt, and (white) phone. We'll call it a lipstick newbie fail.

Product: Maybelline Color Sensational Creamy Matte Lipstick in Divine Wine ($7)

From the second I was handed this lipstick, I was apprehensive. I didn't want to look like Kylie Jenner sporting a solid brown lip, but I have to say, I was pleasantly surprised. I don't think I'll ever wear this exact shade again because chocolate (excuse me, "Choco-Licious") isn't my shade, but it was creamy, wore well, and didn't get all over my clothes. Win.

Product: Revlon Lustrous Lipstick in Choco-Licious ($5)

This felt, looked, and smelled like I was rubbing strawberry jam on my lips rather than lipstick. It seemed to melt the second the product touched my pucker, which made for a slippery challenge (I accepted and owned it). My main complaint in the moment was how sheer it was, as I was getting used to all of the bold hues, but that didn't stop me from loving the way it looked. It was this day that I realized I was becoming more of a beauty girl than I ever thought possible, as the words "bold" and "lip" would have never been a combo I used while discussing my makeup routine in the past.

Product: Yves Saint Laurent Beauty Rouge Volupte Shine Lipstick in Rose in Sound ($36)

This is totally the type of pale cherry red that I would have worn — with caution — before I started this challenge. It's just the right type of shade that it doesn't call too much attention to my lips — as it's not far off from my natural color — and it's got a sheer quality that makes applying it more like putting on chapstick than a bold lipstick. It kept my lips feeling soft and moisturized all day, which was a plus. I'd totally rock it on a regular basis.

Product: Lauren + Vanessa Lipstick in French Red ($24)

After 10 days of nonstop lipstick-wearing, my pout was starting to feel a bit dry (as I mentioned earlier, this is not uncommon), so this beautiful matte red-orange lipstick was perhaps not the best choice for this day. My next issue came after I decided to take down a huge slice of pizza (as I've been known to do on more than one occasion). After that endeavor, it looked like I had an ombré lip (not in a cute way), as all of the color had faded from the middle of my lips. That being said, I felt amazing in this hue because it was vibrant like the reds I was getting used to (who would have thought?!) but had a bit of bright orange for added flair. I'll wear it again for sure.

Product: MAC Lipstick in Ruby Woo ($17)

This deep purple lipstick intimidated me something fierce before I applied it. But then it went on like velvet, smelled fruity and delicious, and made my teeth look whiter than they are, so I learned the hard way not to judge a lippy by its cover. However, I found throughout this experiment that I am definitely more of a red lip kinda girl, so rather than going for this purple again, I would likely explore Lancome's counter for something a bit more "me."

Product: Lancome Color Design Lipstick in Into the Rapture ($23)

My first takeaway after these 12 days out of my comfort zone is that I definitely can pull off lipstick (even though I spent years convincing myself otherwise). Second, from here on out, a bold lip will be a really fun way for me to change up my beauty routine every once in a while, but it's not going to be an everyday thing for me, and that's OK.