Lipstick Vs. Pie: Slice Up Your Life

Challenge accepted

Another season, another lipstick challenge! Ice cream meant the odds were stacked against our lipstick shades, but we totally conquered the dessert. Then we lived to tell the tale of how our lip color—and our teeth—remained intact when faced with candy apples. But all year long, we have been waiting for this day. No, not Thanksgiving. That ship has sailed (see what we did there?!), and now we can focus on the main plate at the table: pie.

As with shades of lipstick, there are so many different flavors of pie from which to choose. We decided to keep it simple and go with a classic pumpkin, baked by our very own digital design director, Liz Riccardi. (She happens to be a pie pro.) Now that 2016 is coming to an end, we'll have to whip up more dishes to put our lips to the test in the new year.

See how our lipsticks held up as we fed ourselves gigantic slices of pie in the gallery, below.

Katherine Martinez, E-commerce Director

This vintage '90s icy blue shade by Urban Decay looks exactly like one that led to me being grounded for the first time ever. I was 11 years old and determined to make a She's All That-style entrance at my fifth grade "graduation" ceremony; I had metallic butterfly clips, a drawstring peasant neckline dress, and a pair of sick black Mary Janes all ready to go. Makeup was a big no-no in my house, so I sneakily applied an icy lipstick I had bought (with pocket change) from Claire's on the way to the auditorium. The jig was up when my dad saw my iridescent lips reflecting enough light from the stage to fry a small ant colony. I was promptly punished.

How did Frostbite hold up? Based on people's curious glances on the way home from the shoot, it seems my lips were still a very shiny blue. Also, the pie was BOMB. I don't think it's fair to pick a winner here.

Urban Decay

, Vice Lipstick Vintage Capsule Collection in 'Frostbite,' $17, available at 


Jenna Igneri, Fashion Market Assistant

I’ve never really had a good experience with natural or organic lipsticks until I came across this brand. While the texture is super creamy (and smells like fresh fruit, which makes sense, given that's what it's made from mainly), this lipstick packs some serious pigment power. While I didn’t expect it to last through eating pie because of how light the formula is, it actually managed to leave a lasting stain—essential for anyone who plans on stuffing themselves with pie (and everything else) this holiday season.

100% Pure, Cocoa Butter Semi-Matte Lipstick in ‘Tempest,’ $29, available at 100% Pure.

Irina Grechko, Digital Content Editor

When it comes to lip color, I layer lip glosses over lipsticks over lip pencils in fear of smudging the color off mid-bite, -meeting, -conversation… you get the picture. When it came to this taste test, in the name of fair beauty experimentation, I applied the lipstick—from the new Lips & Boys collection, that takes names from 50 men that Tom Ford finds most inspiring—on its own. Not only was I obsessed with the color, which was a perfect complement to the pumpkin pie, but it didn’t budge even a little bit from my pout. Definitely worth the price tag—especially come party season.

Tom Ford, Lips & Boys Lip Color in ‘Ben,’ $36, available at Tom Ford.

Erica Fieldman, Sales Assistant

This may be hard to believe, but I actually find lipstick to be intimidating. I usually try to apply it about 50 times (no exaggeration), and, as a result, I end up having to redo the entire lower half of my face because I just utterly fail. But when pie was offered along with wearing lipstick, clearly I was all for it. Surprisingly enough, when I went to apply it in the bathroom mirror with utter fear, I found that the Context Sweet Emotion lipstick went on without a glitch. I walked with confidence back to the studio and chowed down on my pie with no shame. Besides rubbing off on the fork, the Context Sweet Emotion lipstick lasted an impressive amount of time and gave me the confidence to boot.

Context Skin, Matte Lipstick in 'Sweet Emotion,' $20, available at Context Skin.

Austen Tosone, Editorial Assistant

Anyone who knows me knows that I'm a huge cheerleader of Stila's liquid lipsticks. I discovered them earlier this year and have never looked back. I'm a firm believer that really amazing lipstick should be able to withstand any meal—all the way through dessert. That's why I decided to put Stila's formula up against an end-of-Thanksgiving slice of pie. Not only was the pie delicious, but the lipstick did not budge. At an event hours after the photo shoot, someone even complimented me on it. I applied it a few minutes before I ate and made sure to put a layer of Aquaphor on first. With this lipstick it's till death—or makeup wipe—do us part. 

Stila Cosmetics

, Stay All Day Liquid 


in 'Fiery,' $24, available at 

Stila Cosmetics


Sydney Gore, Digital Editorial Assistant

I rarely wear color on my lips, so to go green was a very bold move. With this shade specifically, I felt like I was embodying a little bit of Aaliyah in the music video for "Are You That Somebody." This lipstick has become my designated item when I'm not in the mood to wear any other makeup because it immediately stands out, so people don't look anywhere else on my face. Pie is my favorite dessert, so I was extremely excited about this shoot. The lipstick would have held up if I carefully fed myself tiny bites, but that is not how I like to eat my pie. By the time we finished, there were green smears all over the plastic fork. Love the color, but won't be wearing it for a casual bite to eat unless matcha is on the table. (Literally.)

Urban Decay

, Vice Lipstick in 'Junkie,' $17, available at