Apply here to win a Microsoft Ugly Sweater. It's uglier than ever
- Reference: 1764680415
- News link: https://www.theregister.co.uk/2025/12/02/microsoft_ugly_sweater_competition/
- Source link:
Compared to previous incarnations, 2025's jerseys are a slightly more sober affair.
There are three. The Artifact Sweater features a selection of Microsoft's Ghosts of Christmas Past, from the Internet Explorer and MSN logos through the strangely retro-cool Clippy assistant, and what looks a lot like a Minecraft Creeper. There's one celebrating the Zune, and another for Xbox.
Microsoft confirms it found a way to make Crocs even uglier – with Windows XP and Clippy [1]READ MORE
We got our talons on the Artifact Sweater with its multitude of icons. It's almost like someone asked Copilot to spray a sweater with iconography, though if that were true, the result would probably also lack a head hole and sport three arms.
[2]
To give you an idea (pic: Microsoft)
While the packaging has lost the retro-cheese of the XP-themed sweater of yesteryear, this XL-sized garment is sealed and ready to put the family off their Christmas meal.
Want one, and have a UK address for us to send it to? All Reg readers need to do is speak their brains. Microsoft turned 50 this year. When do you reckon we hit peak Microsoft, and why?
[3]
Was it with BASIC in the 1970s? The Microsoft Mouse of the 1980s? The [4]infamous Blue Screen of Death moment , live on stage in the 1990s? Or then-CEO Steve Ballmer's " [5]Developers, developers, developers, developers " performance in 2000?
[6]
[7]
Or something else?
It's all rather Dickensian. One could imagine CEO Satya Nadella being visited by three ghosts: Microsoft Past, Microsoft Present, and the tattered remains of a popped balloon with the letters A and I still visible standing in for the Ghost of Christmas Yet To Come.
[8]Lack shame? Fancy some festive Windows knitwear? We've got your back
[9]Share your 2024 tech forecasts (wrong answers only) to win a terrible sweater
[10]Nostalgia for XP sells out Microsoft's 2023 'Windows Ugly Sweater'
[11]The winner of last year's Windows Ugly Sweater is ...
In Charles Dickens' A Christmas Carol, the Ghost of Christmas Past seemed to be having a lot more fun than the present and future, and it's easy to draw a parallel with Microsoft. For all the sweaty exertions of Ballmer and the company's controversial [12]stack ranking policy , the Microsoft of yesteryear seemed a jollier place. Today it's desperately trying stick Copilot into everything, calling to mind Bob Cratchit hard at work while Ebenezer Scrooge looks on, obsessed with shareholder value filling his moneybox.
So, as the company celebrates its 50th year, take a look back at its past and ponder... over all those decades, when and what was peak Microsoft?
[13]
The Artifact Sweater sold out "in record time," according to Microsoft. But there's a still a way you can inflict some Microsoft festive fun on your nearest and dearest. Add your comment by the end of December 5, and we'll pick a winner and pop an XL Artifact Sweater in the post in time for Christmas dinner. ®
Get our [14]Tech Resources
[1] https://www.theregister.com/2025/10/02/microsoft_crocs_confirmed/
[2] https://regmedia.co.uk/2025/12/02/ms_ugly_sweater.jpg
[3] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offbeat/front&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=2&c=2aS8bLXuukYlQ4dvL8GymhQAAAIA&t=ct%3Dns%26unitnum%3D2%26raptor%3Dcondor%26pos%3Dtop%26test%3D0
[4] https://www.theregister.com/2018/04/20/windows_98_comdex_bsod_video/
[5] https://www.theregister.com/2013/08/24/top_10_steve_ballmer_quotes_from_microsoft_history/
[6] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offbeat/front&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44aS8bLXuukYlQ4dvL8GymhQAAAIA&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[7] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offbeat/front&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=3&c=33aS8bLXuukYlQ4dvL8GymhQAAAIA&t=ct%3Dns%26unitnum%3D3%26raptor%3Deagle%26pos%3Dmid%26test%3D0
[8] https://www.theregister.com/2021/12/10/win_a_sweater/
[9] https://www.theregister.com/2023/11/28/ms_paint_sweater_competition/
[10] https://www.theregister.com/2023/11/30/windows_ugly_sweater_2023/
[11] https://www.theregister.com/2024/12/25/windows_ugly_sweaters/
[12] https://www.theregister.com/2025/10/20/hiring_firing_microsoft_plummer/
[13] https://pubads.g.doubleclick.net/gampad/jump?co=1&iu=/6978/reg_offbeat/front&sz=300x50%7C300x100%7C300x250%7C300x251%7C300x252%7C300x600%7C300x601&tile=4&c=44aS8bLXuukYlQ4dvL8GymhQAAAIA&t=ct%3Dns%26unitnum%3D4%26raptor%3Dfalcon%26pos%3Dmid%26test%3D0
[14] https://whitepapers.theregister.com/
Me too. I'd actually pay someone NOT to send me this sweater!
pay someone
> I'd actually pay someone NOT to send me this sweater!
Just provide your bank account details, and I promise to only take what I regard as fair recompense for not sending you this sweater. Merry Xmas (without the xmas sweater).
Do you have to set a jumper on the motherboard to win?
You need to drain the battery, smash the screen, remove the RAM and put all remains in the shredder to prevent any wins from being recorded on the (wrong) address.
and you may need to drop a stitch, or two,... three
Pop
Start it up
[1]M$'s peak moment was a bunch of nerds dancing on stage. The last time any of it was actually endearing.
[1] https://www.youtube.com/watch?v=lAkuJXGldrM
Dave Cutler's last scion
Windows NT 3.51 was the last serious OS that Microsoft produced before the GDI was moved into the kernel. Everything since has had an element of comedy about it, whether intentional or not.
Re: Dave Cutler's last scion
Gotta love NT 4 and their plug and pray!
Size XL. I presume that's American XL. XXXXXL for anyone else.
Peak MS...
October 27th 1955...
(https://en.wikipedia.org/wiki/Bill_Gates)
I'll be warm under my coat
A coat of three arms?
Peak Microsoft is the short-lived Windows phone. They already had a decent product in Windows mobile, but then an arrogant lack of innovation caused it to fall behind when, first Blackberry, then Apple and Google raced right past them, so they bought Nokia and produced the actually fantastic Windows Phone, brilliant devices - then even had a funeral for iphone. Got next to Zero traction because they were so late to the game and ultimately wrote off the whole division....
I miss Windows mobile too, if for no other reason than to keep Android and Apple honest. There needs to be an actual third vendor in the cellphone space.
Hell, I'd even welcome Blackberry back, if they were willing to step up and make an actual go of it - and I hated them waybackwhen.
I liked Windows Mobile, and for a while it was the best option for business use, then Microsoft lost interest or dropped the ball and even their own apps weren't getting updated.
Work wise we were heavily Blackberry with a few Nokia dumb phones around, mainly due to the benefits of BES reducing data volumes, once that all changed and iPhones became common I was pressured into changing and couldn't really argue!
I'm going to say Windows 2000 Server. I had a local installation running dev versions of my websites far longer than I should have done.
Things have gone downhill ever since...
Send it to OutsideXbox/OutsideXtra
Jane would rock that sweater.
Cardigans always remind me of whales..
Cardigan always reminds me of Wales.
1996 - Exchange 4 and the associated version of Outlook - IMHO the only reason that Windows is still around as the dominant business desktop. By managing eventually to all but wipe out Notes and Groupwise, that locked most of the business world into MS Office and thereby into Windows. (Exchange 4.0 was a sod for exploding without warning, and often a complete bitch to restore properly, but that's the fun of being in IT...)
Interestingly MS don't seem to understand that by slowly shifting the code behind Outlook from native Windows to web-based, that could eventually break the need for most enterprises to standardise on Windows
The real "year of Linux on the desktop" might not now be too far away... (much like Nuclear Fusion ツ)
A pint for the FREE WEAR byline
The mention of Zune gave me flashbacks to pundits predicting it WAS the new iPod KILLER.
Thankfully this comment isn't funny so I won't be receiving the woolly awfulness.
I was thinking - swimming with sharks, but - like for most things in life - [1]Malcolm has it fully covered.
[1] https://www.youtube.com/watch?v=IMaTQ3Ov-RE
Flushing $7.6bn down the drain buying Nokia and then telling them how to do phones using a crappy photocopy of Apples homework. Writing the whole thing off within 2 years.
Mind you the competition is pretty hot. The $26bn they spaffed on the uber-spam/bullshit engine that is LinkedIn has to be the biggest lump of money ever spent on making yourself even less popular than you already were.
This is a pattern they seem to be repeating with Blizzard so we may not have seen peak MS yet, especially if the AI bubble bursts, maybe OpenAI will turn out to be peak MS.
I'd prefer a coat
I'd prefer a coat to a sweater, that way, I have something to protect me from the clouds.
Now, If only we could find something to protect against the AI.
Looking at the sweater, it shows how many things, that they thought were important are now completely irrelevant to us.
Xbox 360
[1] Xbox 360
[1] https://www.theguardian.com/games/2025/nov/26/how-the-xbox-360-almost-won-the-console-war
"It's almost like someone asked Copilot to spray a sweater with iconography, though if that were true, the result would probably also lack a head hole and sport three arms."
So give it to someone in the Army...
Who cares?
I'm just here for the swag ;)
(on a more serious note - I'm around windows 8 - when they made their first big forays into SaaS (Dynamics and so on)
“ When do you reckon we hit peak Microsoft, and why?”
‘Do’ seems to imply future not past.
Which suggests when will MS surpass themselves: I suspect it will be with the update to Windows 12, which will be Copilot (aka AI0 assisted. Were we can expect “Clippy” wanting to be helpful, will in “preparing your system for upgrade” delete the hard disk in readiness before downloading the new install file…
Fields of green, skies of blue
The Windows XP backrop will always symbolise 'peak Microsoft' for me. Even if it wasn't.
At the other end of the rack we have Windows 8 Metro start screen. Shudders and nightmares guaranteed.
It looks like you are trying to win a contest...
Would you like some help with that?
Noooooooooooo!
I want this for "ugly Christmas sweater" contests (icon)
Peak MS to me was when we had to start caring about Microsoft at all -- mid-to-late 1980s DOS days: To go with our PC clone, Dad got a real IBM PC DOS set from work (manuals in custom-sized binders with 5-1/4 inch "'diskette" pockets, all in a cardboard case, all beige/pale pink) -- I believe it was 2.1. But my older brother quickly found out he couldn't play the latest sneakernet games without an upgrade, and it had to be "genuine" MS-DOS (we mostly used 3.3, maybe also tried 4.something).
That was peak: Microsoft or bust. Computers at school that weren't Apple had DOS, mostly to use WordPerfect, even into high school (mid-90s). I could even fit my own DOS files on a 3-1/2 inch disk and reboot into my own ANSI.sys boot screen / menu and play some games [1].
Windows (3.1) was just a (slow) add-on until it started taking over everything, especially with Win95 [2]. It's all been downhill since.
Bootnotes:
1) Mostly runtimes from QBasic like Nibbles and Gorilla, back when the chips were slow enough.
2) And when Win95 hit, the whole school switched at once and forced us into MS Office from there on (save for Pagemaker for the student newspaper plus the proprietary yearbook layout program).
Micro$oft peaked when they released Clippy.
And I would quite like the jumper, and I promise to wear it the day my wife goes in to labour for our second child which is due 23rd December. I can provide photographic proof. Given how it's been during the scans, there is every chance it'll just turn up at the most in opportune time - when I'm sat down for Christmas Dinner lunch wearing that jumper.
Make my kid's christmas great! For the first time anyway.
I want it as I have no life or style and had Bill Gates poster on my bedroom wall and this will go with my Novell Netware bed T-Shirt that has as many holes it did.
Windows 95 Surely?
For me it has to be a launch event where you had Gates, Balmer et al. on stage trying to be cool dancing to the Rolling Stones prior to sheeples lining up to buy the new OS shiny at midnight.
Peak Microsoft twas when Gandalfs hair was still brown and his beard was mere stuble :)
Subjective
Of course, the "peak" for Microsoft will always be subjective. Some people may say it's Windows 7, some Windows XP SP3 and others Windows 98 SE SP2.
Then there's Office. For me, I feel that Word 6 and Excel 4 offered everything that I have ever needed in a word processor and spreadsheet application, and there is no need for all the added-on bloat in subsequent versions.
So, how about this? A stripped down version of each with the basic functions only for normal users, sold at a reduced price. Let's call them Word and Excel. Then, additional "extra large" versions with all the added bells and whistles that they currently have for the premium users, with an "extra large" price tag, too.
Let's call them Word XL and Excel XL.
Re: Subjective
They had a stripped down all-in-one package, Microsoft Works (and if that isn't an oxymoron I don't know what is! :) ). I first encountered it in probably the early 90s when it came free with a new PC and it wasn't too bad for the basics. Having looked I'm slightly surprised it lasted until 2009.
Stolen
Steve Ballmer telling the world that "The most common format of music on an iPod is 'stolen'" (https://www.theregister.com/2004/10/04/ballmer_ipod_thieves/).
Pure Microsoft: insult your (potential) customers ("You guys are thieves!"), and demonstrate a willful ignorance of the underlying technology ('stolen' is a format?!).
The nadir of Ballmerism in a highly competitive field.
It has to be Microsoft's 25th anniversary event in September 2000 with Steve Balmer doing his Monkey Boy Dance, running on stage yelling "I LOVE THIS COMPANY!!!" (not to be confused with his sweaty "DEVELOPERS DEVELOPERS DEVELOPERS"! dance a few months before in July, which was almost peak but not quite)
Best years were in the past
April 1,1975. Microsoft was founded by BG & PA April 4, 1975.
Or June 24, 1981. Microsoft was incorparated June 25, 1981
Gimme that Microshaft sweater. I need something to wear to my LUG.
Ah, the good old Christmas jumper. I'd be more than interested in one of these hideously unfashionable garments if only to be worn to our Christmas Party. Like the good old Windows ME I expect to be crashing within the first couple of hours, so to have something to wear that will advertise this would be superb!
Peak Microsoft was undoubtedly MS-DOS in 1981. Which makes it as old as I am, and I just can't fault it.
Perfect to win office wrong sweater contest
This one would definitely make me win the office wrong Xmas sweater competition during the Xmas drinks session.
So 2 wins in 1 time bad sweater and too drunk to even remember having worn it ;)
Need this for my Canonical corporate Ugly Sweater contest
My girlfriend is always stealing my sweaters...
But if I take one of her dresses, suddenly "we need to talk"
Win10
I have worked with MS OSes since DOS 6.2.
My faves were 95, 98, NT4, 2000, XP, 7, & 10.
Out of these 10 is the greatest. Stable & sleek enough to run nicely on most modern hardware.
11 is a travesty, Lord save us from what comes next...
Merry Christmas! Blessings, Walruzoar
I'm actually afraid to comment in case I win