In the spectrum of parties, the office holiday party is its own beast and is arguably the toughest to navigate. Since we are smack dab in the middle of office holiday party season (there is even a movie about it, and no less than the New York Times has weighed in on the subject) it is important to be prepared. You need to be ready for someone low on the corporate ladder getting too wasted and saying inappropriate things (and someone higher up on that ladder doing the exact same thing but getting in much less trouble for it). You also should be prepped, both mentally and physically, for some really embarassing dance moves, perhaps even bad karaoke. And there will definitely be that guy who refuses to throw in the towel at the end of the night, trying to lure co-workers to the after-after-party back at his place, so remember to just say no.

The office party even presents a unique set of style challenges. We’ve all seen that person who gets way too dressed up when that is definitely not what is called for. But going the opposite direction is a bad move as well. So if you’re trying to figure out what to wear, it might be the perfect time to give the ugly Christmas sweater a try. What started as an eyesore in old family photos developed an air of ironic cool, and has now morphed into a fully mainstream staple.

But finding the right sweater isn’t easy. You want something that is “cool ugly” not just “ugly ugly.” In situations such as this, I find it helpful to rely on the helpful acronym, WWGKD, which stands for “What would Ghostface Killah do?” (Duh.) This year, a lot hip-hop artists (and Mike Tyson, who is most definitely hip-hop) have released their own versions of the ugly Christmas sweater that are vastly superior to the generic ones you find everywhere else. So if you are looking to win your office holiday party by stunting in the best ugly Christmas sweater, here are the ones you need to cop.

Wu-Tang! No one does lavish like the national treasure that is Ghostface Killah. So when the rapper known as Tony Starks/Pretty Toney makes an ugly Christmas sweater, you know it’s going to be outstanding. There are so many levels to this thing, from the Wu logo to the killer bees to the eagle immortalized on Ghostface’s gold bracelet. Every time you look at it, you find something new that makes you smile.



The Illmatic rapper has his own clothing label HSTRY and took a decidedly more woke approach to his ugly sweater (technically, it’s a sweatshirt). Referencing the protest of Colin Kapernick and others who kneel during the national anthem, the sweatshirt, which comes in three colors, shows Santa taking a knee alongside images of raised fists.

It isn’t a sweater and it isn’t all that ugly, but I live in fear of pissing off the Bey-hive (did you see what they did to poor Rachel Ray?). The hoodie’s message “I sleigh all day” is both festive and empowering.
2 Chainz Shop

2 Chainz Shop

2 Chainz is a veteran of the ugly Christmas sweater game. His Dabbin’ Santa character was a huge success last year and the Atlanta rapper came back this year with even more options. Some of the limited editions like a weed-inspired one and a Dabbin’ Hannukah Harry have already sold out, but plenty of other iterations showing St. Nicholas sticking his head into his elbow crease are still available.


It isn’t usually easy for celebrities to poke fun at themselves, but Mike Tyson does it exceptionally well. Being secure in the knowledge that he could still kick just about anyone’s ass must help. This ugly sweater celebrates some of the many things that make Iron Mike so great, from his lisp (“Merry Crithmith”) to his pet white tiger to his epic face tattoo.
Daylight Curfew

Daylight Curfew

A lot more people came to know Run The Jewels’ Killer Mike this year because of the election and his support of Bernie Sanders. But Killer Mike and his RTJ partner El-P are first and foremost talented lyricists with a very sharp wit, as evidenced by their pun-y “Run The Yules” holiday sweatshirt.

Justin Tejada is a writer and editor based in New York City. Follow him on Twitter at @just_tejada and Instagram at @justin_tejada.