In case you hadn’t noticed, the holiday run-up has officially begun, and it’s the time of year when every company begins its relentless assault on your newsfeed and email inboxes with as much whimsy and good cheer as it can muster. While for many this is something of an unwelcome barrage of forced bon-homie, there is the occasional bit of holiday marketing that elicits a genuine smile. 

As far as that goes, we’ve always been partial to the holiday tradition of the Windows ugly sweater, and the good news is the 2023 version has just dropped and by ugly sweater standards it’s virtually tasteful. 

Look at it. The majesty. The nostalgia. The wave of good will and sentiment that washes over you as you remember a simpler time, when taskbars were blue, Windows had a sensible naming scheme, and default desktop wallpapers were the thing that gave you an overwhelming sense of calm. Windows XP was here. Everything was going to be ok.

Just me then? Anyway, as far as the “ugly” factor goes on the seasonal Windows Ugly Sweater, this thing is more of a work of art. Bliss has become iconic over the years, and this sweater is less likely to elicit the correct reaction of horror and instead create a feeling of genuine rose-tinted nostalgia towards desktops past. 

This being the case, let us remind ourselves of some of the more egregious examples of Windows ugly sweaters of yore, so that we may revel in their glory once again.

2018 – The beginning of an art form

Things started off simply enough in 2018, with an almost tasteful (who am I kidding) Windows 95 logo and fetching diamond shapes. An establishment of the form as you will, and the basis for all Windows ugly sweaters to come. 

2019 – A true ugliness begins to emerge

Now that’s more like it. Stare in awe and wonder at the eye-searing vision of Windows XP in knitwear form, marvel at the colour combinations that swirl in front of your eyes like technicolour vomit on an ’80s arcade carpet. A truly beautiful example of the ugly holiday sweater, and regarded as a stone-cold classic. Probably.

2020 – An all-time ugly classic

It’s MS Paint’s turn in the holiday season of 2020, and given the state of the world in the year previous there’s something genuinely heart-warming about seeing an ugly sweater that simply goes for plain old terrible as an aesthetic. Look at the snowflake around the logo. The little tool icons running down the sleeves. It’s iconic, this one, and may be the finest we’ll ever see. Seminal.   

2021 – The horror, the horror

Now we’re just getting surreal. I like to imagine the meeting where this design was first unveiled. There sit the Microsoft execs in low-lit gloom around a big table, smoking cigars (they definitely didn’t). An intern approaches the front of the room and prepares a projector slide.  “And on a lighter note, here’s this year’s ugly holiday sweater design for your approval”.

The slide clicks. Outside the door, you can hear only howls.

2022 – An ugliness of a different kind

It may just be me, but this might be the only piece of clothing that is capable of throwing me into a genuine blinding rage upon its viewing, such is the reaction I receive when gazing upon the inane grinning visage of that most torturous of assistants, Clippy. Only BonsiBuddy elicits more vitriol, and now that I’ve said it, I hope I didn’t give anyone any ideas.

Ugly, most certainly. But if anyone wears it to the office holiday party, I may have to leave the room.

And then of course, that brings us to the modern day. By comparison, this most recent addition to the ugly sweater line-up barely registers on the Richter scale of offensiveness, and instead resides on the “virtually tasteful” end of the metric. You could almost wear it in public without comment, although perhaps that’s pushing it too far. Nevertheless, if you want one they’re currently available on the Xbox gear shop for a somewhat teeth-clenching £70/$70, but in all honesty, what price fashion.

You’re sure to stand out this holiday season nonetheless. Surprise your family with a whole matching set. What a wonderfully blissful festive morning that would be.