The Best Holiday Sweaters in Pop Culture History

Holiday sweaters, whether viewed as adorable or hideous, have become a massive part of the world we live in, both in real life and in Hollywood. Sometimes they play a vital role on a character seen in a television show or iconic movie or they’re part of a fabulous ensemble worn by an A-list star as they make their way through town. Regardless, the holiday sweater is an eye-catching piece of clothing we enjoy wearing and seeing others rock during this time of year.

Today we’re taking a look back at the ones that grabbed our attention the most. So kick back and scroll through our list of the best holiday sweaters in pop culture history.

It’s been a stressful year, but at least you can count on Hollywood to come through with the holiday cheer. After all, what’s more relaxing than watching an overworked woman fall in love with a Christmas tree farmer? So decompress with All the Jingle Ladies, our guide to the best holiday movies.

Bridget Jones’s Diary (2001)

Sure, Colin Firth is all kinds of attractive no matter what he’s wearing. But his role of Mark Darcy took a fashion foot backwards for Bridget Jones (Renee Zellwegger) when she saw him in a green holiday sweater that had a deer splashed across the middle.

Dr. Seuss’ How The Grinch Stole Christmas (2000)

Jim Carrey getting into character as The Grinch himself was already impressive given the amount of makeup and prosthetics he was seen wearing throughout. His look only got that much more next-level during a scene where he wore an over-the-top holiday sweater with “Ho, ho, ho” written across the bottom.

Almost Christmas (2016)

This holiday movie about a dysfunctional family coming together for Christmas features an incredible cast with so many of your favorites, including Gabrielle Union, Mo’Nique, and Danny Glover. So why not dress them all up in matching sweaters for the movie poster? How festive! (Even if their faces say otherwise…)

Step Brothers (2008)

Sure, you have two powerhouse comedic efforts courtesy of funnymen Will Ferrell and John C. Reilly, but there’s also the amazing holiday fashion seen from the latter during this 2008 film. Reilly was the definition of adorable when he wore a top that was designed as a Christmas landscape, with reindeer and boughs of holly. Aww.

National Lampoon’s Christmas Vacation (1989)

Yes, this movie is a constant train wreck with everything going wrong for Clark (Chevy Chase) as the film progresses. But Chase still managed to look festive during one scene with his moronic cousin Eddie (Randy Quaid) with a striped holiday sweater, even as his world continues to crumble.

Ugly Betty (2006)

Season one, episode 10—titled “Fake Plastic Snow”—of Ugly Betty finds the Mode office in full holiday-party-planning mode. Of course, that comes with all the comedy and drama you know well from the series. The real highlight? Betty’s adorable snowman sweater.

David Beckham

First, try to look at what Beckham is wearing before being entranced by the David Beckham of it all. The legendary soccer star channeled Kit Harington’s Game of Thrones role Jon Snow during a memorable holiday-related Instagram snap.

The Santa Clause 3 (2006)

Okay, this one’s a vest, but it 100% deserves a spot on this list. Judge Reinhold wore one of the ugliest holiday contraptions in this film. It’s a piece of clothing that could be considered so wrong yet so right with its seemingly endless stripes, all of which have a different color or pattern to it.

The Santa Clause 3 (2006)

We couldn’t have a list like this and not include something Tim Allen wore in this beloved franchise. He, just like Reinhold, also sported a bizarre sweater in the third film.

Mindy Kaling (2018)

A lot of celebrities have holiday spirit, but Mindy Kaling may top the list. Remember her incredible “Wreath Witherspoon” pun on The Mindy Project? If you still need more proof, check out this Instagram from the writer, author, actor, and producer, which she captioned, “You can never be overly decorated for the holidays.”

Deck the Halls (2006)

Remember that scene in The Hills where someone said Whitney Port’s outfit was too “matchy matchy?” Matthew Broderick, Kristin Davis, and their pretend kids in this 2006 film took that term to a whole new level with their matching holiday sweaters.

Howie Mandel

The America’s Got Talent host represented the millions celebrating Hanukkah by repping a cool blue holiday sweater with “Challah” written in the middle. The top was also adorned with a big piece of challah bread and a miniature version of Howie popping out the middle of it wearing a Menorah-inspired T-shirt. So much to look at here, folks.

Seth Cohen in The O.C.

Two words: Chrismukkah sweater.

Whoopi Goldberg (2018)

Did you know in 2016 Whoopi Goldberg had her own holiday sweater line for Lord & Taylor and Hudson’s Bay called “Ugly”? Well, now you do! As you can see during this 2018 appearance on Watch What Happens Live with Andy Cohen and Tyler Perry, the talk show host’s love of festive knits runs deep.

Ozzy Osbourne

One of the biggest rock legends took his holiday season to the max when he wore a Gremlins-inspired sweater that had a massive ’80s look to it. Pair that with him making one of his signature crazy faces, and you are left with something truly spectacular to look at.

Home Alone (1990)

This Macaulay Culkin film is one of the best holiday movies ever made. The heathered red knit sweater his character is seen wearing throughout as he tries to dodge criminals Joe Pesci and Daniel Stern is no doubt an iconic fashion piece in cinematic history.

You are welcome for the holiday fashion inspo.

Originally Appeared on Glamour