4 Unconventional Beauty Looks To Try This Holiday Season

It doesn’t take a whole lot to conjure up a typical holiday beauty look — there’s usually a cherry-red lip, sometimes a cat-eye, and almost always, glitter in the form of a light-catching metallic eyeshadow or trophy-gold highlighter. It’s a look we turn to year after year, holiday party after holiday party, because 1) it can always be counted on for being on-theme — it’s timeless in that sense, 2) it complements any and all festive attire, and 3) it’s deeply comforting as all things are when they’re ritualistic in nature. 

But as much as we love a classic, reliable look, there's something absolutely thrilling about taking the experimental, unexpected route. That’s why, in partnership with Ulta Beauty, we tasked four R29 editors to demand more from their holiday beauty this season, to push themselves out of their comfort zone, and to present a high-risk, high-reward look that defy conventions and expectations, and in doing so, challenge the very definition of holiday beauty. Take a look at their fire, grid-worthy looks and read all about their process, below.

My typical holiday beauty look is… “Champagne glitter eyeshadow, fluttery lashes, and a gorgeous warm rosy lip.”

This year, I wanted to try… “A bright eyeliner moment. I think it’s such a fun, cool way to wear colorful makeup if bold colorful eyeshadow feels like a lot. As much as I love a classic winged liner, I really wanted to push my creativity with a look that incorporated my favorite color: emerald green.” 

What I love about this look: “No matter what eye shape you have, you can tailor this look to work for you. My eyes are pretty round, so I actually had to take the shape higher on the brow bone than I initially thought to properly frame my eye. If you have more almond-shaped eyes or hooded lids, then you can probably create a more elongated shape. This is a look that would definitely turn heads at a holiday party — and no one would show up with the same makeup.”

The process: “I first applied a shimmery ColourPop eyeshadow all over the lid, outlined eyeliner shape with Stila liquid eyeliner before tracing it over with a deep green Urban Decay eyeliner pencil (you can apply the pencil directly or with a small angled liner brush to blend and feather out the shape). Next, eyeshadows: Lancôme shadow stick along the lower lashline, and the colors 'Not a Bot' and 'Static' from Urban Decay's Naked Cyber eyeshadow palette in the inner corners of my eyes. 

“For the rest of my look: Anastasia Beverly Hills gel for brows, Tarte concealer where needed, Benefit Cosmetics blush on cheekbones, ColourPop highlighter on high points of face, a few swipes of Tarte mascara, and finish with a bold lip: a scarlet red Nars lip pencil and a deep red MAC liquid lipstick.

What I learned: “You cannot rush a look like this one. Getting the shape right with the liquid liner was by far the trickiest step, since you're laying the foundation of the look. From there, you're just adding color and blending. I went slow and steady, making adjustments and cleaning up the shape with a cotton swab and micellar water where needed. Liner looks (especially graphic shapes) are definitely easy to mess up since the goal is to look as symmetrical as possible. Just go little by little and adjust each side until everything looks perfect.”

The response so far: “I live with my boyfriend, so he was the first person I saw after completing this look. He was super into it and loved how artsy it looked compared to my everyday, minimal makeup. After snapping some selfies, I sent a sneak peek to a few friends and they were all very supportive and excited.”

My final thoughts: “I loved it! It felt cool and modern, but still festive with the hint of frosty silver glitter in the inner corners. I think it’s unique — definitely not your typical holiday makeup look — and depending on the color, you can tailor it for any going-out occasion.”

My typical holiday beauty look is…“Simple but always with a pop of color. I’m usually always dressed up for the holidays, but this year I want to take it one step further.” 

This year, I wanted to try… “To step out of my comfort zone. This look pushes me because it’s unconventional. I’ve never committed to one color for my entire face before, but I was game to try a monochromatic look — glittery pink eyes with pink eyeliner — and carrying the shade to my cheeks and lips.”

What I love about this look: “It incorporates my favorite color: pink.”

The process: “After doing my skin and brows, I used the color 'Chic Yeah' from a Morphe eyeshadow palette and blended it with the color 'Power Oh' on my lids and finished the eye look with a bright, bubblegum pink ColourPop’s liquid liner and Benefit mascara. Next, I contoured with a blush from Tarte and Benefit, blending them together to create a pretty pink shade. I finished my look with a super-glossy lip using a Too Faced lip plumper and a Tarte lip gloss.”

What I learned: “I don’t have a particular technique worth noting, but I did learn how hard it is to apply eyeliner — it took a lot of time and patience, but I did it.”

The response so far: “Interesting because I don’t normally wear a lot of makeup. Reactions were like, ‘Wow, she’s wearing eyeliner.” Friends and family were shocked but supportive.”

My final thoughts: “I was definitely afraid I was going to mess up. I was so proud of myself when I finished the look; I loved the outcome. I want to play around with more colors. Next, I would love to do an all sky blue eyeshadow with a pop of blush.” 

My typical holiday beauty look is… “Dare I say, basic. I like all things shiny — shimmer on the eyes, highlight on the cheeks, gloss on the lips, and blush — because I think it looks great on camera with flash. The summer is all about natural lighting, but the holidays are always so dark on the East Coast that I like to do looks that look great with flash.” 

This year, I wanted to try… “A look that used glitter and pigments, and was in one word: glam. One particular makeup artist and the l monochromatic winged eyeshadow look all over TikTok inspired this look.”

What I love about this look: “I’m perpetually late, so I usually stick to one easy look for efficiency. But I love the way this turned out and the impact it has in photos. I might start getting ready an hour earlier when I go out so I can show off this new look. While it did take me a long time, I thought it was also an easy way to serve a bold eye (just use tape!). The wide outlined wing and the gems definitely make it stand out. It's so fun.” 

The process: “I did my face first (using a Lancome foundation, Tarte concealer, and Anastasia Beverly Hills bronzer), but next time, I’ll do it like the pros and start with eyeshadow. For my eyes, I started with Urban Decay primer and then placed two pieces of tape to ensure a sharp wing at the end (I recommend you do this before foundation, because I had to go back and fix this). I applied the pink-orange shimmer shade 'Love + Warhol' from ColourPop's eyeshadow palette, layered on an iridescent shade 'Cyberspace' from Urban Decay's Naked Cyber palette, and used ColourPop's copper shade 'Cahuenga' as the outline. 

“I lined my lips with a NYX lip pencil, filled it in with a nude Stila liquid lipstick, and finally layered NYX's lip gloss on top. Then I popped on some blush from Anastasia Beverly Hills to add some color to my cheeks, and for the finishing touch: false lashes from Kiss and crystal gems from Ardell that I applied with a clear lash adhesive.”

What I learned: “Definitely use tape if you're not a professional. It's a surefire way to make your lines sharp and defined around the eyes. I learned that for bold looks, definitely do eyeshadow before foundation and use concealer for cleanup.”

The response so far: “My one friend called me a ‘vision,’ which made me giggle and others applauded me for making my eyeshadow even on both sides. My friends are practically beauty gurus so this made me feel like I did a good job.”

My final thoughts: “I was stressed during the entire process because the look was such a big commitment for me. I kept thinking about what I would do if I ended up looking like a complete clown. But, as I stuck with it I had more fun seeing the results and watching the look come to life. When I finished, I first questioned if it looked good (after looking at yourself in the mirror for an hour it can be hard to tell). But as I started taking pictures, I felt like I really pulled it off and looked, quite frankly, hot. I would wear it to a friend's holiday party, out to the club, or a regular party. I think it would also be extra fun to ring in the new year with sparkly gems under my eyes.”

My typical holiday beauty look is… “Nothing special. For most occasions, besides a change in lip gloss, I do a natural makeup look that takes less than 10 minutes.” 

This year, I wanted to try… “A bold lip because that's not typical for me. This is a look that definitely pushed me out of my comfort zone in every way: I don't wear foundation, I only occasionally play around with eyeshadow, I never use eyeliner (let alone white eyeliner), and I stay away from loud lip colors. I also saw someone on a show do their eyeshadow like this, and I had to try. I thought the white eyeliner would be the extra-needed element to make the look more unconventional.”

What I love about this look: “I look so cool. I love how I can look like a different person and still look like myself at the same time. It's a cool feeling.” 

The process: "After foundation and concealer, I applied eyeshadow from the blue-centric Morphe palette, starting with the color 'Swagger' as my base, layering on 'Preview,' and then blending 'So Dazzlin'' into the corner crease. I used white Stila liquid eyeliner and drew arrows on the corner of each eye, lined my lids with black liner, applied the glittery blue 'Sapphired Up' eyeshadow on the inner corner of each eye, and finished with the volume mascara from Essence. For my lips, I outlined with a scarlet red Nars matte lip pencil and then filled them in with a red matte liquid lipstick from MAC. And last but not least: a pink Tarte blush."

What I learned: “I definitely had to practice beforehand. I didn't use any special techniques; the secret is just steady hands.”

The response so far: “Everyone was really into it. I was scared because they don't usually see me with a full face of makeup like this, but I've gotten some pretty animated responses. The encouragement really makes me want to play with different makeup looks more often.” 

My final thoughts: “I was so very scared of messing up. I was worried it would look terrible because it was the first time I was putting all the pieces of the look together, and I wasn’t sure if I’d pull it off. But I was pleasantly surprised, and I might try out different eyeshadow and eyeliner colors in the future!”