The Unexpectedly Meaningful Stories Behind These 5 Holiday Makeup Looks

I am, by nature, a bit of a beauty queen. I don't exactly spend my days in a full face of makeup or prance around my kitchen in heels. But anyone who knows me would not be at all shocked by my fully stocked skin-care fridge, my 100-plus nail polish collection, and my plethora of perfumes. This is not to say that I’ll ever reject a hoodie-and-sweatpants combo and a fresh face, but my love for adornments, pampering, and all things pretty is deeply rooted in my fondest memories of watching my paternal grandmother and aunt dress up for the holidays. 

As a young girl, pies, sides, and wine glasses would whizz by my head as tipsy adults played cards, belly laughed, and crinkled my grandparents’ plastic-wrapped sofas. But I only kept my eyes trained on those two women. Leading up to the family affair, my aunt would spend hours at the salon to achieve the perfect hairstyle (a blowout and press). My grandmother, on the other hand, would rifle through her extensive makeup collection (after she cooked, of course) to put on her face with which she’ll dazzle the gaggle of guests who'd roll through the entire day. I’ll always associate the season with the unforgettable scent of White Diamonds by Elizabeth Taylor mixed with collard greens in the air. In those moments, beauty was their pride. Every detail, from rouge lips to red tips, enhanced their femininity, magnetism, and confidence. And from then on, I was hooked.

Since the elders got older and the youngins got grown, huge holiday shindigs are no longer the norm for either side of my family. But I maintain that feeling of pride every time I get fly for the holidays — if only to strut to my living room and watch football. In some ways, those holiday beauty habits are a tradition for me to carry on the love they had in themselves and our family. Beauty connects us all during the holidays. That’s why, in partnership with Ulta Beauty, R29 Unbothered editors have shared how beauty played a role in their last meaningful holiday memory and how they plan to keep that spirit alive this season. Read their stories below. 

“November 2019 was my last Friendsgiving before the pandemic. My friends own a shop in Bed-Stuy that has also become a community hub, so they hosted an intimate Friendsgiving potluck. We set up tables and everyone brought a dish. It was such a warm evening spent among chosen family and loved ones. And it also sparked the beginning of new friendships for people meeting one another for the first time. It's such a valued space in our community, and my friends have been the glue that held us together, especially in the last two years. My makeup that evening was bold, festive, and fun: I paired a multicolored headwrap with a matte red lip (I don't wear a lot of makeup, but a bold red lip has always been my holiday go-to). My look represented exactly how it felt to share such a fantastic evening with a group of my favorite people: vibrant and alive.

“That memory means so much to me because it was my last holiday gathering, and it solidified the validity in having a chosen family. Just because we may not always be able to spend the holidays with our biological families, quality time spent with our friends can mean just as much. Love exists in both spaces.

“My family and I aren't traveling this year, so I'll most likely spend the holidays with friends — possibly another Friendsgiving(!), or a meal at a friend's home, making up for all the time we haven't spent together over the last two years. And I'm hoping to make more memories and establish new traditions with a look that blends old with the new: loc jewels and decorations (I started my second loc journey in early 2020; a scalp serum like this one has helped) that I have yet to wear in public, some eyeshadow from Mented Cosmetics, and my go-to holiday red lip using Juvia's Place's long-lasting matte lipstick."

“My family is Jamaican, and one Christmas a few years ago, I spent two long weeks with my mom's side at my cousin's house. Huge is an understatement for how big my family is, and to have so much love under one roof was simply euphoric. Jamaica has always been a home away from home for me, but going back as an adult created an even stronger bond with my culture and family. I was raised as an only child by a single mother, and I always felt fulfilled with it being just the two of us (I literally had the best childhood ever). I never understood family group chats — how do you have so many family members you're that close to? But after reconnecting with my family after a decade, I had a sudden longing for familial affection I never knew I needed. There was something about my bossy aunt telling everyone what to do or my youngest cousins screaming and fighting that I couldn't help but enjoy. Now, my appreciation for family has made a complete 180, and yes, I'm part of my family's group chat now.

“Beauty played a big role at that reunion because I wasn't coming back as a baby, but as a grown woman. Sharing our Western beauty trends — from my no-makeup makeup looks to my ready-to-go curls — with my Caribbean family was a highlight. I loved the ‘oohs’ and ‘ahhs’ I got from my aunties before they demanded that I give them the same look. But it was my youngest cousin's sweet smile and dainty accent that made me feel like I was her Fairy Beauty Guru Godmother.

“This Christmas will be spent at my place in L.A., and we'll have the same traditions as last year: A huge breakfast on Christmas morning with everyday American dishes (scrambled eggs, bacon, and pancakes), along with plates from our culture (ackee and salt fish, fried dumplings, fried plantains, and salt fish fritter and cornmeal porridge — the latter reminds me the most of my Jamaican culture). And dinner will consist of mostly every meat you can think of (oxtails, curry goat, jerk chicken).

"Cooking and beauty are both about prep work; the meat needs to be seasoned — and so do I! My prep process will include deep conditioning my hair (my pick: this curl-defining shampoo/leave-in conditioner combo from Pattern) and wrapping it up in a towel while I work in the kitchen, so by dinner, my curls will be bouncy and vibrant — just like how they were in the Caribbean. My makeup, too, will be similar: a skin care-forward approach with dewy, glassy skin, highlighter from Juvia's Place, and clear lip gloss.

"And after dinner, we'll probably hop on Zoom with the family, so everyone can talk over each other while mom and her sisters argue over whose Christmas cake tastes better (my mom's, duh).”

“The week between Christmas and New Year’s Eve in 2019 ranks as the number-one most meaningful holiday memory — my sister got married in January 2020, and my mom made her wedding dress, so I spent that time in the basement watching my sister stand for fittings while my mom made adjustments. Normally, during the holidays, I see all of my old friends, get caught up in nostalgia, and have a grand time drinking at all the places we couldn’t get into in high school. But that year, the family was so focused on the upcoming wedding, it didn’t leave a lot of time for social visits. But honestly, I wouldn’t have had it any other way. I was able to relax, pamper myself with face masks and pedicures, and spend quality time with my family. 

“When my sister got engaged the year before, I told her that I wanted to gift her her wedding scent. She has always been all about fragrances — so much so that most of my memories surrounding our childhood have a fragrance attached to them (whenever I catch a whiff of  Mugler’s Alien I’m instantly transported back to high school, and the time we spent driving in the car we shared). I gave her a perfume discovery set, so she could figure out what scent she wanted for the occasion, and now, whenever I smell the fragrance — one with strong floral notes that remind us of the gardenias planted in the garden of our childhood home — that she wore throughout her wedding weekend, it reminds me of the time we spent together celebrating with family.

"All of my beauty, especially during the holiday season, comes from my mother's beauty collection. She loves BareMinerals, so before I would leave the house I'd always dust Warmth all over my face and neck for a glow that's reminiscent of summer. She also instilled in me the need for mascara (my favorite: Urban Decay's Perversion), lip gloss, and a good brow. Even though we'll be communicating over FaceTime (at least for the first half of the holiday season), I know my makeup look will be the first thing she will comment on — and I plan to look my best to make sure she worries a little less about me."

“My most recent and meaningful holiday memory was Christmas 2018. I hadn't been home in over a year since moving to New York, which was the longest time I had been away from my mom. The return was so warm and inviting, because not only did I get to see her, but I also saw family members I hadn't seen in years. It felt like a small family reunion. Looking back, it was one of the last times that a majority of my family was together and carefree. At the time, I was on a natural hair journey, and since it was at the end of the year, it felt like a new beginning. I remember focusing on the health of my hair (with products like this curl-hydrating butter cream from tgin or these hair-healthy essentials from Briogeo) and finding new beauty looks to go with my new cut (I settled on a red lip).

“This year, my holiday plans are still up in the air, but I have every intention to create opportunities to meet and engage with more people. Over the last couple of years I’ve learned the importance of having quality people around me, and I want to use every chance I get to create memories, start new traditions, whether that's throwing a holiday party or attending an ugly sweater party.

"I would love to step into these new traditions feeling beautiful and confident, and for me, that's with a red lip (the color of love, like this vibrant lipstick shade from Buxom, and I'm all about self-love) and curls (because curls are my crown) — the very same beauty elements from three years ago."

“In March 2020, I went home to visit my parents in Virginia right before lockdown happened — I had no idea I'd wind up quarantining with them for more than a year. That Christmas, there was still so much uncertainty (despite news of vaccines), so we poured our hearts into decorating like we would in a regular year. My mom, dad, and I dressed in matching red Christmas sweaters that read, ‘Merry Christmas 2020,’ complete with red Santa hats, and sang carols together for their church's virtual Christmas celebration.

“Beauty played a huge role in helping me feel like it was a normal Christmas. I had little reason to dress up and wear makeup during quarantine, but knowing my mom and I were going to sing a duet for the church's Christmas program meant I was going to go all out with a full face, my favorite dramatic eyelashes from Eyelure, and a soft red lip. Sitting down at my vanity and doing my full beauty routine (starting with my skin care, which includes this charcoal mask from Origins) reminded me that the holiday was more than just a regular day — it was a special time with my family that I was so fortunate to have and still be able to celebrate when so many of us were separated.

“Though I've been back in L.A. since April, I'm heading back home to hunker down with my folks again for the holidays and pouring myself into all the festivities that come with the season: singing duets, decorating the tree, baking cookies (we might have to bring back the matching Christmas sweatshirts as well — so long as I can wear my Santa hat, the most voluminous lashes, and a red lip). The pandemic has taught me how fragile life is, and there are just no other people I'd rather spend my favorite time of year with than my parents.”