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

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.

“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.”

“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.”

“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.”

“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.”

“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.”

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