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5 Fashion Rules to Get You Through the Holiday Season in Style

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Right about now is when the countdown starts ticking for the holiday madness to begin. Soon our calendars will be packed with cookie exchanges, Friendsgiving dinners, holiday cocktail parties and more festive get-togethers, and the challenge of trying to find something to wear to all these events will undoubtedly take up far too much brain space. To make things a bit easier this year, we’ve put together a list of five rules for holiday dressing (don’t worry, they’re really more like guidelines) to make outfit planning far less stressful. That way you can instead focus on what really matters: finally finding the perfect gift for your incredibly picky sister.

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1. Lean Into the Spirit of the Season

Even if you tend to lean toward a neutral color palette the rest of the year, consider adding some pops of silver or red to jazz things up for the holidays. It doesn’t even need to be big—a pine green clutch or orange leaf-inspired pair of flats will go a long way. On the flip side, this is the one time of year you get to pull out those ugly Christmas sweaters, so if you want to go big with all the kitschiest clothing you own, we say do it.

Shop similar styles: Boden Fair Isle Christmas Sweater ($140); Naadam Scenic Fair Isle Cashmere Sweater ($195); Tacky Elves Ugly Christmas Sweater ($50); Kiel James Patrick Santa's New Sleigh Sweater ($128); Urban Renewal Vintage Fair Isle Sweater ($49)

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2. This Probably Isn’t the Time to Go Super Sexy

There are absolutely exceptions to this “rule,” but your office holiday party or dinner with Grandma and all your nieces and nephews isn’t the place for super-low necklines and micro miniskirts. Save the va-va-voom pieces for New Year’s with your friends or date night with your partner and instead embrace comfier styles with a bit more coverage for the family get-togethers.

Shop similar styles: White House Black Market Velvet Editor Blazer ($220); J.Crew Regent Blazer ($198); Banana Republic Rivoli Corduroy Blazer ($250; $200); Hutch Pleated Tulle Skirt ($168); Boden Tulle Midi Skirt ($110); Anthropologie Ruffled Tulle Skirt ($148)

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3. It Is, However, the Time to Go Glam

Velvet and sequins and feathers, oh my! If ever there was a time to go all in on sparkle and shine, it’s now. To make these luxe, evening-ready pieces feel more appropriate for day, try balancing them with very casual basics. We’re talking plain white tees, cotton button-ups, minimalist sneakers and/or all the denim (jackets, shirts, jeans, etc.). Then, for a nighttime event, just swap in some heels or more tulle, tartan plaid or other embellished pieces and you’ll be looking fabulous and feeling festive.

Shop similar styles: H&M Sequin Wrap Dress ($75); Michael Costello Dionne Midi Dress ($318); Show Me Your Mumu Maddison Dress ($198); Sabina Musayev Calantha Dress ($320; $224); ASOS Frill Sequin Mini Dress ($220)

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4. Comfort Is King

A lot of the holiday season centers around eating—Thanksgiving dinner, cookie exchanges, New Year’s drinks, etc.—so we can pretty much guarantee you will be infinitely happier if you choose clothing that is comfortable both before and after a big meal. If the waistband is pinching before you’ve even left the house, consider changing into something else. That way you can focus on catching up with your loved ones and not get distracted by your outfit.

Shop similar styles: L’Agence Kenzie Double-Breasted Blazer ($795) and Lane Flared Trousers ($695); J.Crew Slim-Fit Drapey Shirt ($90) and Gwen Mini Slip Skirt ($80); Sleeper Black Tie Pajama with Double Feathers Set ($390); Eloquii Flare-Sleeve Sweater ($75) and Sweater Column Skirt ($65); Caballero Deep V-Neck Maxi Dress ($248)

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5. When In Doubt, Do Classic Head-to-Toe Black

It doesn’t matter whether you prefer a little black dress, a coordinating suit or a cozy sweater and some Audrey Hepburn-inspired cropped trousers, wearing head-to-toe black is a surefire way to look chic and elegant. And, as an added bonus, it serves as the perfect base to play around with kooky accessories like shoulder-grazing statement earrings, rainbow beaded handbags or feather-adorned heels. Of course, you also can’t go wrong with some pearl studs and a simple wristwatch either—it’s totally up to you.

Shop similar styles: Eliza J Sweater Dress ($138); Reformation Fraiser Dress ($248); Chico’s Eyelet Balloon-Sleeve Dress ($139); Veronica Beard Ruched Dress ($450)

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