Top row: Tarte Exposed, Rimmel by Kate Moss #08
Bottom row: Urban Decay Catfight, Lipstick Queen Medieval, Dolce & Gabbana Dahlia

This month, Cup of Jo editor Caroline accepted the challenge to wear a different lipstick every day—from red to blue to black. This week, per your suggestions, we took the photos in the same spot each day. The light varied slightly, depending on the hour of day, but hopefully you can compare the colors more easily! Here’s her recap…

1. Tarte LipSurgence Matte Lip Tint in Exposed
This line promises to make your lips “6000% more moisturized in 28 days.” That sounded like crazy talk to me, but it did make my lips appear fuller. I wore this to dinner at our favorite local spot, where I hoped I looked gamine in the flickering tea lights. “That color doesn’t really look like anything,” said the boyfriend, who quickly added, “and that’s not a bad thing.” I loved the super matte finish, which made my face feel polished.

2. Rimmel Lasting Finish by Kate Moss #08
I wore this lipstick on a day with nothing special planned, yet it elevated my everyday look and made buying groceries and walking the dog feel sort of glamorous. The dusty rose color is perfect for times when you want to look effortlessly sexy (like you didn’t try too hard—or even better, like you didn’t try at all). I felt like I was channeling the lipstick’s namesake supermodel, who seemingly rolls out of bed looking great. Incredibly, this lipstick is UNDER FIVE DOLLARS. But pretending to be Kate Moss is priceless.

3. Urban Decay Revolution Lipstick in Catfight
Confession: Despite its not-so-pretty name, this bright pink lipstick made me feel…pretty! (I almost broke into the song from West Side Story, but controlled myself because, you know, social expectations.) This was my lipstick of choice for grabbing drinks with old college friends (when I wanted to look like I’d improved with age). More important, I felt great wearing it since all Revolution lipsticks are not just gorgeously pigmented, but vegan and cruelty-free. After all, kindness trumps prettiness any day.

4. Lipstick Queen in Medieval
During the day, I was stopped by not one, not two, but three strangers (three strangers!) who asked what lipstick I was wearing. Fascinating fact: This sheer red was inspired by women in medieval times, who would stain their lips with lemons, since wearing lipstick was considered a sin. The color wears off fairly easily, so you’ll need to reapply. But if you want dewy, rosy lips (and, really, who doesn’t?), I’d highly recommend it.

5. Dolce & Gabbana Classic Cream Lipstick in Dahlia
“That’s intense!” said Joanna, the moment she saw me. But intensity is good, right? These new lipsticks contain fifty percent emollients, which is a fancy way of saying they won’t dry out your lips. But what I REALLY love about Dolce & Gabbana lipsticks are their bold, dramatic colors. This dark orchid shade made me walk a little taller and put a little more swagger in my step. I’ll definitely wear this whenever I want to feel like a femme fatale (which may or may not be embarrassingly often).

…And that concludes the lipstick challenge! If you missed them, here are weeks one, two, and three. In the end, my favorites were the versatile NARS Manhunt and my everyday staple, Laura Mercier Healthy Lips. Thanks again for all of your amazing comments and suggestions these past few weeks! Please stay tuned for more fun challenges, coming up soon…

P.S. Hair tutorials and how to get rid of a pimple.