How To Dress For Every Kind Of Holiday Party

It’s the same story every year: Halloween hits and suddenly the same autumn season that seemed slow-going a few weeks ago shifts into a fast-paced blur of holiday spirit and festive activities. There are decorations to put up, gifts to shop for, and cookies to bake. Meanwhile, your calendar suddenly starts filling up with more holiday events than you can ever possibly attend (not that you won’t try to!). And as each celebration looms closer and closer you realize you have zero idea how to dress for it.

Lucky for you, the LoveShackFancy team does. As you may have caught on, getting dolled up for, well… any circumstance is kind of our thing—so we definitely have more than a few thoughts on what to wear to a holiday party. A foolproof first step? Start with a statement dress or skirt you feel 1000 percent fabulous in, and are confident in styling multiple ways if needed. The Flince Embellished Mini Bubble Skirt is a brilliant example of this as it both works with the matching Gloriana Embellished Corset  and heels. Or, should you want to skew in a cozy and casual direction, it also plays well with a slouchy cashmere sweater pullover and boots.

Indeed, having one perfect piece on hand will serve as your wardrobe insurance policy all season, especially if you become too busy to buy anything else. Should you have the time and budget, though, it’s worth stocking up on some alternative wardrobe options. The holiday season comes but once a year, so why not do it up right? December’s bustling social calendar is, after all, the ultimate excuse to shop for something new to see and be seen in, particularly if you don’t want to be photographed in the same thing more than a few times.

Whichever route you’re looking to take though, we’re here to help. Below, our we’re compiled 6 must-try looks for every sort of dress code in the upcoming months, complete with styling tips that don’t require buying an entirely new closet of clothes. Take notes and look forward to never overthinking what to wear to a holiday party again.

The Raucous Office Bash

Whether your place of work comes with a strict dress code or it’s an anything goes situation, the annual office holiday party has its own set of rules: namely, looking way chicer than any of your co-workers knew was possible. An easy way to achieve this? A leggy pair of pinstripe trousers (ahem, check out the Garelle Pants) and a slinky little camisole. Adding a designer jacket  is optional, but if you’re going to wear one, go for something cropped and sharp-shouldered (our Icarus or Pendine styles would do the trick). Now all that’s missing is a towering pair of heels that you’d never dare commute in—but feel free to use the excuse of a company event to expense your Uber ride home.

The Cookies & Cocoa Meet-up

Any affair centered around carbohydrates is definitely the kind of low-key get-together in which you could go for jeans and an “ugly” Christmas sweater and call it a day. But why invest in an unflattering pullover emblazoned with Frosty that you’ll only wear once? Especially when there are plenty of far more enticing alternatives out there? The Parson Alpaca-Blend Ribbon Pullover, for one, would make a statement of equal measure without screaming “themed party” (and still be comfortable after round three at the peanut butter blossom plate… whoops!). It’s also worth considering jazzier denim than usual—like, say, the bow-bedecked Dessa Pants—paired with a simple top. And if all else fails, you can never go wrong with a classic fair isle cardigan, especially when it’s in a less expected color scheme, like pastel tones. Pair your look with a little holiday cheer by adding a pop of red lipstick or a fun scarf to truly embrace the spirit of the season.

Dessa Bow Jeans	Parson Ribbon Pullover

The Extended Family Gathering

A big get-together at home always ignites the same question: How do you dress practically for a whole lot of sitting on the couch and still look cute in all your mom’s photos? (Because you already know she’s going to post pictures of you on Facebook without permission.) A sweater dress is a fairly foolproof way to go, as it looks totally polished, but is soft and stretchy enough for a full night of eating, drinking, and lounging. You might also consider a skirt with a forgiving waistband and, as is the case with the Shayda Lace Skirt, a matching top. In short, you want to look for pieces that look like you’ve really put a lot of time and effort into putting them together for your loved ones, but actually require hardly any more effort than slipping on your favorite T-shirt and soft pants.

Shayda Lace Mini Skirt	Ruffle Mini Tartan Skirt

The Big Black Tie Fête

Ah, the agony and ecstasy of being invited to a truly over-the-top fancy holiday party. On one hand—hooray!—you have a golden opportunity to go completely all out with your look! On the other hand… wow, it can be a lot of pressure to get all dressed up. So why not make it way easier on yourself with a one-and-done cocktail dress? A long gown, especially in a bold print or color, always leaves a lasting impression, and the tartan Rialto Dress  certainly lives up to that promise. Or, if you’re all about showing some leg, try channeling your inner Princess Diana with an ’80-inspired LBD, like  the Woodlow Dress, and sheer black hosiery. From there, it’s super easy to wrap up the right of the look: simply add high heels, your most sparkly statement jewelry, and a clutch that’s only just big enough for lipstick and a phone.

Woodlow Bow Mini Dress	Rialto Silk Tartan Dress

The Cocktail Hour With An Ambiguous Dress Code

Few things are more frustrating than being asked to stop by a post-work drinks situation with absolutely zero direction on what the rest of the crowd will be wearing. “Come as you are,” they say, but what if “as you are”  equals wearing jeans and sneakers only to find that everyone else is dressed up? And don’t even get us started on how annoying it is to be the sole mini dress wearer in a sea of denim and knits. In such situations, your best answer is an outfit that can be easily adjusted. Enter: the Bordeaux Vegan Leather Pants. Pair them with a lacy little camisole and cardigan and a pair of heels. If the mood feels more formal you can always lose the sweater and swipe on some red lipstick (bonus points if you have some spangly earrings in the purse to throw on, too.)

Laticia Top	Bordeaux Pants

The Candlelit Dinner Party

The lights are low, the wine is flowing, and the mood is jovial—this is the kind of get together in which you want to look like you put some effort into your holiday look, but not at the expense of your good time (read: anything with a pinchy waistband or corset boning). In this case, a long skip skirt, like the Merado Lace Maxi Skirt  or  Bertha Silk Floral Maxi Skirt, would be ideal, as the silhouette looks polished, but not in a try-hard way. From there, you can either throw on a relaxed sweater (for more casual situations) or a fluid silk camisole (for elegant affairs). Cheers to that!

Merado Skirt	Bertha Silk Skirt