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Ugly Christmas sweaters for every possible occasion

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The best and silliest holiday sweaters aren’t just horrendously ugly. They also pay tribute to the year’s most memorable pop-culture moments—because what could possibly bring more yuletide cheer than a tacky interpretation of José Bautista’s bat flip or Drake’s dorky dance moves? Here, 20 excellent conversation starters.

Ugly Christmas sweaters for every possible occasion

Joey to the world, indeed. $50. Freshbrewedtees.com.

Ugly Christmas sweaters for every possible occasion

This jolly tribute to Josh Donaldson (a.k.a. @BringerOfRain20) is also spot-on. $50. Freshbrewedtees.com.

Ugly Christmas sweaters for every possible occasion

Just so your intentions (leaving the party a.s.a.p.) are as clear as possible. $28. Etsy.ca.

Ugly Christmas sweaters for every possible occasion

Of all the Drizzy-inspired sweaters, we like this pastel number by Toronto brand Shelfies the best. $60. Shelfies.com.

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Ugly Christmas sweaters for every possible occasion

Scratch that. The Grinch’s “Hotline Bling” moves definitely take the cake. $33. Etsy.ca.

Ugly Christmas sweaters for every possible occasion

Here’s Santa’s take on the controversial Kim Kardashian cover. $70. Retrofestive.ca.

Ugly Christmas sweaters for every possible occasion

Praise be to the pizza lords. $60. Shelfies.com.

Ugly Christmas sweaters for every possible occasion

A seasonally appropriate choice for the Force Awakens line. $67. Merchoid.com.

Ugly Christmas sweaters for every possible occasion

Don’t wear this unless you’re up for a spontaneous dance party. $33. Etsy.ca.

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Ugly Christmas sweaters for every possible occasion

Okay, so it’s not technically a Christmas sweater. But for anyone who worships at the altar of Trudeau, this is as spiritual as it gets. $60. Shelfies.com.

Ugly Christmas sweaters for every possible occasion

Because Mean Girls will never stop being culturally relevant. $25. Etsy.ca.

Ugly Christmas sweaters for every possible occasion

Battery-powered swag for a whole new generation of Beliebers. $109. Etsy.com.

Ugly Christmas sweaters for every possible occasion

Mrs. Claus jumps on the dabbing train. $54. 2chainzshop.com.

Ugly Christmas sweaters for every possible occasion

Jon Snow who? Finally, the most underrated Game of Thrones character gets the respect he deserves. $41. Etsy.com.

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Ugly Christmas sweaters for every possible occasion

Only to be worn in jest (obviously). $35. Etsy.ca.

Ugly Christmas sweaters for every possible occasion

Blame Miley for this club-ified take on the North Pole. $28. Etsy.com.

Ugly Christmas sweaters for every possible occasion

Here’s the snuggliest way to cheer for the Raps this winter. $60. Clarktoys.com.

Ugly Christmas sweaters for every possible occasion

Buddy the Elf: as classic a Christmas character as Santa himself. $82. Urbanoutfitters.com.

Ugly Christmas sweaters for every possible occasion

As seen on Katy Perry. $25. hm.com/ca.

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Ugly Christmas sweaters for every possible occasion

And finally, here’s one for loyal Leaf fans. (Warning: it may trigger looks of pure pity). $70. Retrofestive.com.

Jean Grant has been a freelance writer since 2015, covering a range of lifestyle topics like shopping, interiors, wellness and culture for publications like Maclean’s and Toronto Life. She also enjoys working with brands to develop custom content, and shares personal essays through her Substack newsletter, Nobody is Thinking About You.
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