The Complete Ugly Christmas Sweater Guide

A brief history and where, how and when (if ever) to wear one

This post is sponsored by Amazon Fashion.

What is there to say about the ugly Christmas sweater? Really? It’s an item that pretty much speaks for itself. Actually, speaks probably isn’t quite the right word – yells loudly and obnoxiously is a bit more like it. However, over the years and especially recently, the ugly Christmas sweater has become a bona fide thing. Hell, there’s even a guide book for throwing your own ugly Christmas sweater party.

So where did this trend come from? Is it ever okay to wear an ugly Christmas sweater? And, if you’re going to wade into those waters, what’s the best way to do it? Just a few questions we intend to answer here. But, first, let’s start with some history.

A Brief “History” of the Ugly Christmas Sweater

While the ugly Christmas sweater has no documented genesis moment or story, it is widely accepted that the interest in and acceptance of said sweater can be attributed to one Bill Cosby as Cliff Huxtable on Cosby’s eponymous 1980s sitcom. While Cosby’s sweaters were certainly ugly, they weren’t necessarily very Christmasy.

However, that leads us to another one of the ugly Christmas sweater’s defacto progenitors, Chevy Chase as Clark W. Griswold in the modern holiday classic National Lampoon’s Christmas Vacation. One of Griswold’s sweaters, in particular, fits the modern ugly Christmas sweater mold, but almost doesn’t hold a candle to his Christmas tie game!

Despite the ugly Christmas sweater’s appearance in the pop culture consciousness in the late-1980s and early 1990s, that alone can’t account for its burgeoning contemporary popularity. To that we owe another ingredient altogether: nostalgia.

I was born in the late 1970s and I can recall family Christmas gatherings that included all manner of “interesting” though sartorially-questionable garments, including, but not limited to, sweaters. My father, for one, was and still is quite fond of the ugly Christmas socks. I can still vividly recall his red socks with little green Christmas trees on them. As a matter of fact, I think he still has them…

Anyway, the point is that I’m probably not the only one of my generation who can make these types of associations. And thought they’re not the most “stylish” clothing choices, they make you feel something. And nostalgia such as that is one of the central pillars that Christmas is built upon.

Should You Ever Wear An Ugly Christmas Sweater?

The question of whether wearing an ugly Christmas sweater is ever appropriate would seem to be – for this publication, at any rate – an open and shut case. And a quick one at that. But I’m going to go out on a limb and throw you guys a bit of a curveball here. While I’ve got no qualms giving hard and fast advice about certain matters of style, my favorite answer for whenever anyone asks me if something is “okay” is, well, it depends.

In the case of the ugly Christmas sweater, it depends on a couple of factors. First and foremost, what event will you be wearing it to? Here’s where it’s pretty cut and dry. If you’re going to wear one, make 100-percent certain that you’re attending an ugly Christmas sweater-friendly event.

Now what type of event would qualify for that? Here are a few: a designated ugly Christmas sweater party (either at someone’s home or apartment or out at a bar), a close family gathering (not a first holiday with potential in-laws situation) in which you are typically admired and/or known for your quirky or sarcastic sense of humor.

Now how about the events that are off limits? Well, in this category, we’d put just about every other kind of event not included above. Under no circumstances should you wear an ugly Christmas sweater to: an office holiday party, dinner at a restaurant, a last-minute shopping trip to the mall, and so on. You get the idea.

Tips For Pulling Off An Ugly Christmas Sweater

Now if you are going to tempt the devil and don an ugly Christmas sweater, here is some very simple advice for pulling it off. By its very nature, an ugly Christmas sweater is a statement – albeit a tacky and gaudy one – and should be treated like any other statement piece in your wardrobe. What that means is simply to let it stand on its own. Keep the rest of your outfit – well, let’s be honest, we’re just talking about your trousers here – plain. The addition of an OCBD can help “class” the sweater up a bit.

Chime in: Where do you stand on the ugly Christmas sweater?

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo