5 Looks That Will Guarantee You a Spot on the Holiday Best-Dressed List

Sponsor Content Created With Gap


It goes without saying that the burning question, "But what should I wear?" lingers a bit longer this time of year. As soon as November hits, my calendar is immediately flooded with invites until January—but I'm not complaining. I'm a social butterfly, so getting dressed up and chatting with new and old friends, especially during the holidays, excites me.

A major part of this excitement is that all of the upcoming events warrant a shopping spree for pieces that will guarantee me a spot on the holiday best-dressed list. This season, I'm making my shopping a little bit easier by heading to Gap for every occasion. And yes, I mean every occasion: dinner parties, New Year's Eve, gift exchanges, and more. While known for its classic staples, Gap also specializes in standout party pieces, which our editors are eyeing right now. I love putting outfits together, but not without a little bit of inspo from my fellow editors. I asked five of them to style a head-to-toe holiday look using pieces from Gap, and they did not disappoint. Keep scrolling for a look at the on-trend 'fits they put together.


(Image credit: @nataliecantell)

"Apparently, being in your 30s means that the holidays turn into a month of nonstop dinners? Temperatures in New York just fell off the edge of a cliff, so I'm shooting for cozy but elevated outfits."


"These wide-leg Tencel™ trousers are all of that in a nutshell. A moment for the teddy trend, which is such a buzz: I love how the exaggerated lapel of this moto-style silhouette keeps it feeling more polished and evening-ready than some other takes I've seen this season. Obviously, Gap sweaters are always so good, and scooping up a modern knit is an easy seasonal refresh—this under-$70 sweetheart sweater definitely can't be beat."


(Image credit: @indyabrown)

"There are few occasions in which head-to-toe sequin is the standard dress code, so when it comes to New Year's Eve, I absolutely don't shy away from maximum shine." 


"This sequin miniskirt packs a punch in a smaller piece. I love the subtle hint of sparkle on the buttons of this oversize shirt. It's a quieter alternative to full-on glitter or sequins yet every bit as glamorous. Together, these two pieces are an A+ combo."


(Image credit: @katcollings)

"For a gift exchange, my outfit goal is to look laid-back but still polished. I'll rely on the layering duo beloved by fashion girls everywhere: a turtleneck under a collared shirt."


"Adding a silver chain on top will take the styling trick to the next level. I always think of Gap for quality basics and was delighted to find it's also a home for accessories that make my outfit feel party-ready. Sumptuous corduroy pants (truly the fabric of the season) and a pair of smart ankle boots complete my holiday look."


(Image credit: @fitzpatrickerin)

"I really appreciate the fact that I can get such high-quality, stylish, and reasonably priced pieces for the holidays at Gap."


"A work party isn't my favorite place to show a lot of skin, so I'll be wearing a long-sleeved dress and tights. I absolutely love wearing jewel tones for the holidays, so these emerald-green earrings are the perfect festive accessory. I'll finish off the look with a classic black coat and sleek black boots."


(Image credit: @anna_laplaca)

"Let's be honest: Holiday shopping can feel like a sport. So when it comes to checking everyone off my gifting list, I'm prioritizing comfort—period."


"I'm leaning on luxe but easy-to-wear staples such as these corduroy flare jeans and this sherpa-lined moto jacket as my hero pieces. I love how the rich brown color of these corduroys lends a holiday-ready vibe without feeling cliché at all. Plus, the flared-ankle shape pairs flawlessly with these Western ankle boots. It's the perfect combo for a long day of shopping."

Aniyah Morinia
Associate Branded Content Editor
Aniyah Morinia is an NYC-based associate beauty and fashion editor at Who What Wear. She has worked in fashion media since 2018 and joined WWW's branded content team, where she not only writes for some of her favorite brands but also creates content for them. Aniyah will find any excuse to get a photo of her outfit and absolutely loves taking photos. She graduated from the University of Florida in 2020 with a bachlor's degree in public relations and started post-grad life freelancing for EveryStylishGirl, Riot Swim, and Baby Tress. Since starting at Who What Wear, Aniyah has developed a passion for hosting livestreams, working red carpets, and creating TikToks in addition to writing fashion and beauty stories. When Aniyah's not writing or creating content, you can find her exploring Brooklyn and eating her way through the city. She'll never pass up the opportunity to uncover an NYC hidden gem or mix and mingle with her friends (all while swapping holy-grail products, of course).