What to Wear in Order to Upstage Everyone at Your Family Holiday Party

As the snow begins to fall and the chestnuts roast, one thing becomes increasingly clear: the holiday season is officially here! You know what that means, it’s time to dress in a way that will have your family asking, where did you get that weird piece of clothing? Between shopping, gift-giving, and gathering around a roaring fire, one must make sure to continue flexing on your loved ones. The eternal quest to be the best-dressed family member never takes a vacation! Keep reading for some genius ideas to confuse your grandparents and assert that you’re the coolest relative. 

1. A cloak. Nothing says “mysterious cousin” like a cloak, cape, or enormous shawl. With a sweeping wingspan that comes dangerously close to any lit candles, you’ll be the star of any family dinner. With any luck, one of your older and more senile relatives will think you’re in a cult or coven. 

2. Thigh-high Converse. While a bit of a throwback, these classic emo sneakers will have your uncle saying “why are you wearing those?” And isn’t that the goal of any party, to incite a thoughtful conversation? Step into your mom’s house with these bad boys and reignite the flame of your hometown’s most recently closed Hot Topic. 

3. Violently clashing patterns. Nothing says “best dressed” like an outfit that looks like you got dressed in the dark, or drunk, or both. Disorient your cousin’s toddler by creating a confusing visual image. As a bonus, it will mask any spills obtained during dinner and drinks. If you can, mix a plaid or tartan with spots or stripes. Even better, make sure you’re wearing a vintage sweater with cats on it to really seal the deal as “freshest” or “most disturbing” fashion sense.  

4. A beret. Nothing says “loud and most opinionated niece” like a stupid hat. Hint at your worldliness with a jauntily angled head adornment carefully paired with, oh I don’t know, a stupid turtleneck. You’ll have all your aunts asking, “Does she think she’s from France?” If by France you mean a small liberal arts college in New England, then yes! 

5. An ugly holiday sweater. Worn ironically or completely sincerely? Absolutely nobody will be able to tell. Experience the magic of the holiday season through the ugliest garment of all time, surrounded by your loved ones. Here’s a tip: pair it with some chunky jewelry you got at a yard sale or at a specialty Etsy shop to really make a splash! 

Following these guidelines is a surefire way to really impress this year. Whether you’re ringing in the New Year or baking cookies with grandma, you just know that you’re gonna be impossible to ignore. Season’s greetings! 

Callie Webb
Author: Callie Webb
Callie is a comedian, human being, and woman. She has a fondness for George Michael and videos of unlikely animal friendships.