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Just Because November 27th, 2023

7 Best (Er, Worst) Ugly Christmas Sweaters For Men

Just Because November 27th, 2023

This Hurts, But Let’s Have Some Fun!

We know what you’re thinking and before you say anything, we’d like to direct you to a previous post that tells you more than you ever thought you’d need to know about the ugly Christmas sweater, its history, when to wear, how to wear, and should you wear.

Here at HSS, we’ve recently been getting into the holiday spirit and, like it or not, the ugly Christmas sweater is something you just can’t avoid this time of year — it’s like the sartorial (and we use that term very loosely) equivalent of “All I Want For Christmas Is You” or “The Little Drummer Boy.” So, in the spirit of fun and good cheer, we put a call out to our editors to share the favorite/best/worst ugly Christmas sweater picks.


Brian Sacawa

I need to start off by saying that although I do not completely condemn the wearing of the ugly Christmas sweater, there is a time and place — a very, very, very specific time and place — to wear one. Which is not to say that I condone it either! Anyway, now that I’ve offered my little disclaimer, let me introduce you to my favorite ugly Christmas sweater for that very, very, very specific time and place.

As much as my wife rolls her eyes when I suggest watching “National Lampoon’s Christmas Vacation” when ‘tis the season, she loves it every time, particularly the characters Todd (Nicholas Guest) and Margo (Julia Louis-Dreyfus) whom she always suggest we dress up as on Halloween. (We’ve never actually done it.) So if I’m going to wear an ugly Christmas sweater, it would be this one because, for me, at least, it’s an equal-parts cocktail of nostalgia, irony, and good cheer.


Cyrus Schiller

I don’t think anything is as notorious for being wearable camp as the “ugly Christmas sweater.” Indeed, because of its niche, mostly ironic appeal, this bold style choice is usually an impulse purchase that people wear a few times around the holidays, and rarely or never after that. Even though I personally wouldn’t wear one, I understand this appeal and how it fits into classic style.

There’s a lesson this garment can teach us: we all want to make a statement with our clothing, even if it’s a statement we can’t make every day. And why would we want to? The entire point of holidays is that they aren’t every day, and sometimes it’s fun to go wild with your clothing choices.

In that spirit, I think Blizzard Bay makes memorable sweaters that celebrate Christmas kitsch in an interesting and unusual way. Seriously, how can I argue with a line of sweaters that feature the buyer’s choice of sloths, sharks, llamas, or dinosaurs? Reindeer? Please. As a bonus, if you’re like me and want to ease the consumer guilt of buying for the throw-away economy, these sweaters are made out of cotton, unlike their mostly acrylic peers.


Drew Chambers

I’m a die hard Knicks fan (which I wouldn’t wish on my worst enemy), and as such I thought that this basketball ugly sweater was fun. The point of these ugly sweater parties is generally to have something that is a fun talking point and in this way it leads to conversation, and with Christmas day being a big NBA day, maybe some friendly wagering. Pro tip: don’t stand too close to the yule log.


Mark Remillard

A classic Christmas sweater goes perfectly with a classic Christmas movie — and perhaps no Christmas movie is as a classic as ”National Lampoon’s Christmas Vacation” (at least in my household). This particular sweater has it all: festive colors, the snowflake details, and a touch of knit patterning. But the best part is its relative obscurity. There’s no better way to show off your love of all things Christmas and ”Christmas Vacation” than by referencing the line before the famous “I don’t know, Margo” quip. If you wear this to a Christmas party and someone recognizes the line “Why is the carpet all wet Todd?” …well, you should have an instant connection.


Ponzio Oliviero

If one of the reasons for wearing an ugly sweater is to spread a little holiday cheer, then my choice for ugly sweater for the season is this example with the Grinch. It may be an ugly sweater, but c’mon, it’s the Grinch! How can you not love Dr. Seuss’ Grinch?

Multiple generations of children have grown up watching the original animated cartoon, and there have been at least two live-action movies, and countless stage productions of this inimitable character. I even have a Grinch tie which I can’t wait to wear every year to at least one holiday party. I would feel the same with this sweater in the festive wear rotation. This sweater is guaranteed to get comments at any event you attend, and even strangers will give you a nod or a thumbs up if you wear it while doing some of your holiday shopping. You will be the most photographed person at the office party, and everyone will want a selfie with you.

So, if you want to be the wallflower at the next Christmas party, don’t wear this sweater. But if you’d like to put a smile on someone’s face and bring a bit of whimsical nostalgia to the party, then this is the sweater to have.


Tony Gorga

Honestly, outside of the odd pair of socks, I don’t have a whole lot of ‘festive-y’ Christmas garb. But, I’m a secret Star Wars nerd. I appreciate the direction Disney has taken the franchise by engaging the next generation and building a new fanbase. I was particularly impressed by the practical effects of Grogu-“Baby Yoda.” in “The Mandalorian.” Plus, he’s a huge hit with my four-year-old. And, honestly, I kind of want a hat with Yoda ears for my newborn.


Dylan Lucas

The Coofandy Christmas Sweater addresses my biggest issues with ugly sweaters—their unflattering silhouette and lack of versatility. The buttoned mock-neck naturally draws the eye toward the face and away from any excessive holiday weight. Its Nordic pattern broadens the shoulders. The winter themes and wide-color selection can fit anyone’s holiday needs without being relegated to being worn once a season. Whether you pair it with some soft flannel trousers and suede slippers for a winter’s evening at home, or a heartier twill chino and some moc-toe boots for a trek through the snow, this sweater is a great addition to a winter wardrobe.

Throwing An Ugly Christmas Sweater Party?

Stylishly Yours,

He Spoke Style

Over the past 10 years, He Spoke Style has established itself as the leading online destination for premium original men’s style content. Blending information and inspiration, He Spoke Style provides practical style advice, outfit ideas, product reviews, and trend analysis for regular guys interested in menswear. Known for their relatable and distinctly unpretentious voice and approach, Founder Brian Sacawa and his team of writers have become influential in the contemporary menswear conversation, having been quoted and featured in publications such as The New York Times, Wall Street Journal, Business Insider, Esquire, GQ, The Robb Report,, Playboy, The Rake, and The Huffington Post.

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Edited by Rachel Butler


Well, Thanksgiving is over and hopefully you’ve awoken from your tryptophan-enduced slumber ready to hit the ground running full speed ahead into Holiday season proper. However, before you do that you might want to take a moment to check out what’s on offer from some of your favorite menswear brands this Black Friday and Cyber Week. To help save you a little bit of time, we’ve put together this list of the 20 best Black Friday menswear deals out there along with our curated picks from each sale. Enjoy!

That’s right, we’re running a promotion here in Ye Olde HSS Shop and it’s a pretty good one! Take 20-percent off any one item with promo code HOLIDAY20. This code can be used once per customer and cannot be applied to past orders. Offer ends December 31!