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

Bring on the sequins and velvet and kitschy knits

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Let the countdown to the holiday festivities begin! Soon, our calendars will be packed with cookie exchangesFriendsgiving dinners, Christmas movies, cocktail parties and 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 for you this year, I’ve put together a list of five rules for holiday dressing (don’t worry, they’re really more like guidelines) so outfit planning is far less stressful. This way you can focus on what really matters instead: finding the perfect gift for your incredibly picky sister.

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1. Pair Your Holiday Staples with Chic Basics

Everyone loves a good ugly Christmas sweater (or kitschy Santa earrings, candy cane-striped handbags or other overtly holiday-theme items), but there is a way to make them feel polished and festive, rather than just, well, ugly. The key is to pair your holiday-theme pieces with upscale basics, like a little black dress or wide-leg trousers. The two opposing aesthetics blend together surprisingly well to create a look that’s both fun and chic.

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2. Hold Off on the Super Sexy Outfits

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—think midi skirts and blazers, matching knit sets, slip dresses with cozy cardigans—for the family get-togethers.

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3. Don’t Hold Back on the Glam, For Day or Night

Velvet and sequins and feathers, oh my! If ever there was a time to go all in on sparkle and shine, it’s now. There’s also no need to reserve them only for evening events. To make these luxe pieces feel more appropriate for day, try balancing them with very casual basics. I’m talking plain white tees worn over sequin trousers, a denim jacket worn over a feathered frock or jeans worn with an embellished blouse. 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.

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4. Prioritize Comfort

A lot of the holiday season centers around eating—Thanksgiving dinner, cookie exchanges, New Year’s drinks, etc.—so I 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, like a sweater dress, a pair of wide-leg trousers, a cozy matching set or a swingy tent dress. That way you can focus on catching up with your loved ones and not get distracted by your outfit.

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5. When In Doubt, Go for (Mostly) All 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.

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Frequently Asked Questions

What Does Festive Attire Mean on an Invitation?

“Festive” can mean many different things depending on the context, but in terms of a holiday party it most generally means guests are encouraged to lean into the season and embrace all the best holiday pieces in their wardrobes. For a New Year’s get-together that likely means sequins and shine. For a friend-filled Thanksgiving party you should probably lean into autumnal hues like red, orange, yellow and brown.

If you feel really lost, you can always ask the host, but come prepared with specific questions (i.e. don’t just ask “what should I wear?”). They have enough on their plate getting everything together ahead of the big event to worry about your wardrobe. Send a photo of a potential outfit and ask for their thoughts. Or ask something like, “is this sequin minidress and heels-type festive or statement earrings with jeans and a T-shirt-type festive?”

What Is a Christmas Dress Code?

If the theme of the event is “Christmas,” then determining what to wear is simple: anything red or green or both. A host who explicitly lists Christmas as the dress code is likely hoping guests will arrive in holiday sweaters, red-and-green tartans and anything else that feels specifically Christmas-y, so feel free to really lean to the holiday vibes. That said, use your discretion when deciding whether to go fancy, casual, sexy or jokey—is this an event for your kiddo and their friends and friends’ families? Or is it a girls’ night with your college besties?

What Should I Wear to My Office Holiday Party?

Unless you work in a super-artsy field (i.e. fashion design, theater, art galleries), your office holiday party is not the time to go super bold or experimental with your party attire. Avoid anything too low cut, too tight or too short and instead opt for something more like a fancy version your everyday officewear. If you sport sweaters and jeans most days, try a polished cardigan over tailored trousers. If your uniform is a blazer and midi dress, opt for a blazer in a more festive fabric like silk, velvet or leather. When in doubt, black separates or a black dress make for a chic, no-fuss base for party-ready accessories like a colorful silk scarf, rhinestone earrings or red pumps.


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