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When Did Ugly Christmas Sweaters Stop Being Ugly?

When Did Ugly Christmas Sweaters Stop Being Ugly?

Ugly Christmas sweaters used to involve some unholy combination of hot glue, tinsel, and stick-on bows. Then they became commercialized.

I was waiting for the train on the Upper East Side of New York City a couple of weeks ago when I noticed a handsome man leaning against the stair rail. Everything he was wearing was tasteful and vaguely expensive: white Common Projects sneakers, dark jeans, a Tag Heuer watch, and an understated navy wool coat.

From the side, I couldn’t tell who the coat was made by, but it had to be designer. The look was anonymous, but the tailoring was impeccable and the buttons appeared to be genuine horn. Armani, perhaps? I couldn’t see what was underneath the coat, but I figured it had to be something equally stylish: a Loro Piana cashmere sweater or fitted AMI sweatshirt?

Taylor Swift walking down her apartment steps in New York dressed in a navy blue Christmas sweater - not ugly
Taylor Swift sporting a stylish blue Christmas sweater. Image via Shutterstock.

Just then, the train arrived and he turned toward me. What I saw shocked me. He was wearing a navy blue Christmas sweater with Fair Isle patterning and reindeer across the chest. I was so thrown by this seasonal sartorial plot twist that I almost forgot to get on the train. 

Actor Matthew Morrison sporting a Christmas sweater with a cat on a sled

Model Rylan Clark-Neal wearing a Christmas sweater with three gingerbread people

Actor Natalie Cassidy wearing a Christmas sweater with Santa's head and fluffy beard

Actor Lamorne Morris wearing a Christmas sweater with Santa waving to us
Celebrities love to flaunt their ugly Christmas sweaters. Images via Matthew Taplinger/Starpix/Shutterstock, Shutterstock, Jabpromotions/Shutterstock, and Carlos Piaggio/Shutterstock.

Thirty years ago, a sweater like that would have been laughable. The kind of thing you would wear, at most, once a year, and even then only under extreme familial duress.

But these days, more and more, holiday sweaters seem to be making their way out of middle-American family Christmas cards and onto the streets of the country’s most cosmopolitan cities. 

Musician Tom Fletcher wearing a green Christmas sweater with dinosaur singing

Welsh singer Aled Jones wearing a green Christmas sweater with a red reindeer in the middle

Professional boxer Nicola Adams wearing a navy blue Christmas sweater with a dinosaur wearing a Santa hat

Italian singer Andrea Faustini wearing a green Christmas sweater with a gingerbread man in the middle and he seems pretty happy about it
They all seem pretty happy with their choices. Images via Steve Meddle/Shutterstock, Ken McKay/ITV/Shutterstock, Steve Meddle/Shutterstock, and Beretta/Sims/Shutterstock.

I blame hipsters. They love taking an uncool piece of clothing and wearing it ironically . . . until it enters the mainstream, at which point they discard it in favor of some new off-beat trend.

Back When Ugly Was Ugly

Two women running and having fun in the Ugly Christmas Sweater Run in Amsterdam
Two women running in the Ugly Christmas Sweater Run in Amsterdam, of course. Image via BAS CZERWINSKI/EPA-EFE/Shutterstock.

In the early 2000s, you couldn’t throw a fruitcake in Williamsburg during the holiday season without hitting an ugly Christmas sweater-themed party. They were everywhere. And, people really went all out.

They scoured thrift stores for hideous gems from the ‘80s and ‘90s, the tackier and more cringe-worthy the better. Fair Isle-inspired sweaters, like the one I saw the guy on the train platform wearing, were just the tip of the ugly Christmas sweater iceberg.

English TV personality Bobby Cole Norris wearing a black Christmas sweater decorated with Santa, a snowman, snowflakes, candy canes, holly, and a penguin

English singer Stacey Solomon wearing a red extremely gaudy Christmas sweater with a reindeer and lights and what appears to be Christmas ornaments dangling from various locations

Blogger Perez Hilton wearing a light blue Christmas sweater with a giant smiling reindeer on it

Prince Harry sporting a green Christmas sweater with a penguin in the middle while Prince Philip is wearing a maroon Christmas sweater with reindeers - both are wax figures - both look real
Is it just me, or do those wax figures of the Princes look totally real? Images via Beretta/Sims/Shutterstock, Ken McKay/ITV/Shutterstock, Broadimage/Shutterstock, and Ken McKay/ITV/Shutterstock.

There were Christmas tree sweaters with real working lights and Santa sweaters with fluffy white 3-D beards. They were the kinds of things you’d expect to find on a middle-aged kindergarten teacher in a Hallmark movie . . . and no one else.

Often, these sweaters were homemade or—at the very least—home-embellished, which made each one unique and, honestly, kind of special.

As they grew in popularity, they moved out of the thrift stores and into some of the city’s better vintage stores, their prices inching ever higher and higher until, one year, I saw an angel sweater with a hand-painted china-doll face selling at a shop in the village for over $300. 

Singer Miley Cyrus holding a red Christmas sweater with Bill Murray dressed as Santa on it for the premiere of the film A Very Murray Christmas

Director Sofia Coppola wearing a red Christmas sweater with Bill Murray dressed as Santa
If you haven’t seen A Very Murray Christmas, shame on you. Images via Gregory Pace/Shutterstock and Mediapunch/Shutterstock.

That’s when the ugly Christmas sweater trend really reached its peak, in my opinion. Everyone wanted in, and all sorts of new clothing companies started popping up online offering fresh versions of the once maligned sweaters.

Ironically, people still bought them, at first, but the more in on the joke everyone became, the less funny it was.

Singer Meghan Trainor performing in a black sweater/dress with Christmas presents and actual string lights at the top and Christmas ornaments at the bottom

Singer Myleene Klass happy with her choice of red Christmas sweater with her first name embroidered at the top and a snowman underneath

Actor Jessie Usher showing off his bluish Christmas sweater decorated in a scary-looking Santa-Yeti and snowflakes
Nothing says homemade like an ugly Christmas sweater. Images via Matt Baron/Shutterstock, Beretta/Sims/Shutterstock, and Broadimage/Shutterstock.

That’s the thing about irony: upon repeated exposure, it loses its edge, to the point where now, I feel like people genuinely like “ugly Christmas sweaters” as much as any other piece of clothing in their wardrobes. A lot of these sweaters aren’t even that ugly anymore.

Amanda Holden sporting a Game of Thrones-themed sweater with John Snow as Santa with a banner stating
Amanda Holden sporting a clever GOT-themed Christmas sweater. Image via Ken McKay/ITV/Shutterstock.

Maybe it’s just me. Maybe I’ve reached that age all of us eventually reach where clothes cease to be embarrassing or ironic and are merely clothes.

I do still occasionally see a Christmas sweater I think is truly awful, like the one Kate McKinnon wore in 2016’s Office Party, but it doesn’t really bother me more than any other piece of ugly clothing I might see.

Celebrity chef Simon Rimmer wearing a navy blue Christmas sweater decorated with a Christmas tree, presents, and snowflakes
Celebrity chef Simon Rimmer wearing a not ugly, kind of cute Christmas sweater. Image via Steve Meddle/Shutterstock.

And, I can’t help but admire the level of detail and amount of work that goes into them. They’re ugly, but they’re also kind of… charming? Not that I’d ever wear one! They’re not my style. Of course, that being said, I wouldn’t have expected that well-dressed man on the subway to wear one either, and I would happily cop every other piece of his look for myself.

Two members of the band Kingsland Road wearing Christmas sweaters - one is blue with snowflakes and Santa upside-down in a chimney - the other is green with a cute penguin and snowflakes
Image via Beretta/Sims/Shutterstock.

So, maybe it’s just a matter of time before I, too, start stepping out in faux ironic holiday gear. I’ve been known to wear my reindeer antler headband to the grocery store from time to time during the holiday season.

This time next year, I’ll probably be wearing a Santa suit to the laundromat and a light-up reindeer sweater to the opera.

No, actually, that would never happen. I hate the opera.   

Cover image via Broadimage/Shutterstock.

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