The 20 Best Holiday Sweaters, Ranked From Tastefully Cheery to Alarmingly Festive

The best way to spread holiday cheer is to wear it loudly for all to...see

December 11, 2023 9:00 pm
There exists a cannon of festive sweaters that range from tastefully austere to egregiously spirited.
There exists a cannon of festive sweaters that range from tastefully austere to egregiously spirited.

So you want to look festive for the holidays. To wear something that says you’re fun and very into the holidays. Something that doubles as a conversation piece, maybe. Obviously, something that keeps you warm. We’re talking, of course, about the cohort of holiday sweaters that crop up around this time of year.

There are many styles that fall under the “festive” banner, ranging from classy Fair Isle finds — a term we use a lot, even though not all of these sweaters abide by that knitting technique or its Scottish heritage, so think of these as simply colorful knits that fit within a larger winter theme — to charmingly (alarmingly?) red-and-green holiday party scene stealers.

Because we’re all in on merriment, we’ve taken the liberty of rounding up some of the best holiday sweaters for men currently out there. For the sake of wearability, we’ve excluded straight novelty joints from this list, meaning that you can technically wear each and every one of these knits year-round. ‘Tis the damn season.

Fest-o-meter: Christmas is just another day in December

Alex Mill’s Fair Isle Vest isn’t particularly holiday-ish, but it is a tasteful little knit number and by extension an excellent benchmark for this list. With a classic pattern and a cut reminiscent of Paul McCartney’s time in Scotland, it’s a perfectly respectable addition to any friend-of-a-friend shindig you might find yourself at.

Fest-o-meter: “aren’t we a little too old for stockings?”

Another sweater light on merriment and heavy on tasteful vibes, Brooks Bro’s Merino Crewneck’s deep navy and dotted jacquard patterning provides just enough cheer for even the most austere of seasonal gatherings.

Fest-o-meter: a well-prepared Chestnut Praline Latte from Starbucks

There’s not an explicit Christmas holiday tie-in with this chunky Beams+ knit, but, much like the rest of the Japanese label’s wares, the (not so) subtle detailing in the intarsia patterning goes a long way. The weight on this guy is truly insane — the 3 gauge Shetland Wool might as well be a roaring log fire.

Fest-o-meter: all aboard the PJ for a Cancun Christmas

We’re not saying that you’re an automatic Grinch if you can actually afford this luxurious Brunello Cucinelli joint…but you probably are. That being said, you’ll be the best-looking Grinch around.

Fest-o-meter: ice skating (poorly)

The last of the non-festive festive sweaters on this list, Buck Mason’s Italian-sourced Donegal sweater ticks all the white cable knit boxes to winter wonderland perfection. It’s soft to the touch, and just the right amount of slouchy to mask whatever gingerbread-induced paunch you’ve accumulated in the past month.

Fest-o-meter: a December 12th office party

Yetis are culturally agnostic, making them an HR-friendly choice for any office holiday parties you may or may not be forced to attend. Now you just have to worry about getting too drunk and waking up to the “we would have been co-workers in every life” slack.

Fest-o-meter: Tuesday matinee of “The Nutcracker”

There’s just something about this J.Crew Fair Isle that screams holiday. Could it be the Nordic longships, come to bring pagan rituals of pine trees and cider to the very Middle-eastern Abrahamic religions…or maybe it’s the snowflakes?

Fest-o-meter: closing down the hometown bar with buddies you haven’t seen in 12 months

Flint and Tinder’s Fair Isle Cardigan has Hallmark movie love interest written all over it.

Fest-o-meter: snowball fights in Central Park

This 100% Canadian wool Reigning Champ Varsity Sweater is quite literally handknitted by some BC-based grannies, which would explain why it looks like something straight out of A Charlie Brown Christmas.

Fest-o-meter: spiced eggnog by a roaring fire

Now we’re getting somewhere. A proper Fair Isle imported straight from Scotland, this snowy sweater is spun from pure Shetland wool and guaranteed to make holidays merry and bright.

Fest-o-meter: obligatory “It’s a Wonderful life” viewing

This checked mohair sweater from king of Americana Todd Snyder brings a sort of Jimmy Stewart vibe that anti-Christmas chuckleheads really don’t like.

Fest-o-meter: tinsel and popcorn, strung up nice

This gem of a sweater from bespoke darlings Bode doubles nicely for a regular, year-round sweater, but make no mistake: this is a festive knit, through and through.

Fest-o-meter: Caroling in Carol Gardens

Kithmas time is here.

Fest-o-meter: it’s going to be a White Christmas

Ho, ho, ho-baby. Your personal winter wonderland awaits with L.L.Bean’s snowflake-flecked Ragg Wool Sweater. It’s just like the hardy ‘Bean knits that your used to, give or take a few reindeer.

Fest-o-meter: liquored up uncle doling out twenties on Christmas eve

Yes, we’re aware that we said we wouldn’t include novelty sweaters in the intro. We lied. But it was for the sake of Christmas spirit. And vodka-themed apparel.

Fest-o-meter: holiday shopping in Soho

On the first day of Christmas, my true love gave to me…a Polo Bear fleece sweater. (Hint hint.)

Fest-o-meter: *insert Christmas Tree emoji*

Siri, play “Christmas Tree Farm” by Taylor Swift.

Fest-o-meter: basically Kris Kringle cosplay

This Filson Wool vest might as well be straight out of a classic Coke ad, ensuring that you will not only exude aggressively festively energy but will also win brownie points with children and old people alike.

Fest-o-meter: oodles of presents under the tree

Fair isle patterning, red and green trim, argyle striping. French label Drole De Monsieur knows how to do a festive sweater right.

Fest-o-meter: I am 34 and still believe in Santa

Lifestyle influencer and Kennedy wannabe Kiel James Patrick’s sickeningly picture-esque New England Christmases are truly something to behold (we can do it no justice, you’ll have to check it out for yourself) and, through some miracle, the living Polo ad of a model has managed to transpose every bit of holiday magic and semi-offputting WASP-iness into the epitome of a festive sweater.

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