I know some would stop me at the title and tell me: "Hey, no, Windows 7 is not and never will be retro or vintage! It's too modern!" Especially if you stick to a strict 20-year rule for retro/vintage stuff. (Though I'd check the clock, as Vista is fast approaching that magical milestone, and Windows 7 to me just feels like a service pack on steroids.)
At least in my opinion, I think--extreme examples notwithstanding--that you really shouldn't put retro/vintage to a timeline. Especially if you look at other categories like cell phones, where it feels like every device ages in cat years and devices released ten years ago might as well be 20 if you measured them in computing years. (Case in point, 2025 is the 10 year anniversary of the iPhone 6s, the last iPhone that would ship with a headphone jack.)
Anywhooooo we're kinda losing the scope of this piece. We've got a stage to set.
Much of this piece could be applied to both Windows 7 and Mac OS X Snow Leopard. 2009, at least looking back, was an absolutely--as the kids say--goated year for OS releases. It also laid down a very defined demarcation that we wouldn't pick up on for another couple of years: This was the last bastion before The Decline.
The Decline being when both OSes began their downward trajectory into what they are today. Today, macOS feels more known for being a bug-ridden mess than anything, and Windows is known for trying to cram unwanted garbage down your gullet and doing crap to your PC that you didn't approve of it doing.
This began first with OS X: Lion would release in 2011, and this marked the start of something I really wish Apple would stop: A yearly release cadence for Mac OS, much like iOS. While this seemed to be okay at the time, it would later catch up to Apple and result in bugs piling up and this vicious cycle of only being able to really enjoy a bug-free (or rather, a "merely stable but still kinda buggy") OS release for a couple months before Apple was beating down your door begging you to install the new version.
(This is even worse on iOS, where Apple enforces firmware signing so if you take a bad update you usually can't roll back. Further, iOS developers are a lot more expedient about dropping older versions so there's more pressure to upgrade.)
Lion also brought with it the start of the iOS-ification of Mac OS, as it began adopting UI elements from iOS. (It honestly didn't get too bad until many years later, if you think about it. One of the worst changes to macOS, IMO, was the system settings UI change in Ventura. I still struggle with it to this day.)
Windows, on the other hand, would take a wildly different move. Microsoft saw the iPad taking off and seemingly was looking for the next big thing in computing after Netbooks crashed and burned so hard, so they went all in on tablet computing. 2012 saw the launch of Windows 8, and along with it, the revamped Surface line of products.
Microsoft went all in so much that they even forced the tablet UI (lovingly called Metro) regardless of what kind of device you were using. Desktop? Laptop? You got the tablet UI. People, quelle surprise, absolutely hated this. Despite Windows 8's core being much improved over 7, the improvements were overshadowed by the UI being absolutely awful for everyone not on a tablet PC.
Microsoft to their credit did try to run this back, allowing desktop users to revert to a more desktop-friendly UI with Windows 8.1, but at that point the damage had been done and Windows 7 just further entrenched itself as "the good OS". It was Windows XP all over again.
A more complete 180 came with Windows 10, though this began the second chapter of The Decline, for Windows at least: Microsoft moved Windows to become more in line with a Software as a Service model. Updates were forced, there was now Microsoft-supplied bloatware (so you didn't even have to just worry about prebuilt manufacturers loading your OS with that crap anymore!) and the general sentiment of the way 10 operated was "you don't own your computer anymore. We do."
This sentiment was only intensified by people on Windows 7/8/8.1 thinking they were being good eggs and having their automatic updates on, only to be greeted with a stealth upgrade to Windows 10 that happened without their approval, plus the constant nags to upgrade.
(Linux nerds: I can hear your keyboards chattering in the background as you prepare your expected response to that sentiment. Please sit down. It didn't work then, it's not going to work now.)
Much to the chagrin of IT guys everywhere, a lot of us continued riding out Windows 7 for a few more years, some of us even going so far as to upgrade to Windows 8.1 and just installing a Start Menu replacement (like Classic Shell or Start8). Launch Windows 10 was rough. It did what it wanted and it did not care about what the end user wanted. In the middle of a huge project and haven't saved? Microsoft does not give a single fuck, we're updating RIGHT NOW.
It was only a few years in that 10 was tamed and some agency was finally returned to the end user. It still didn't feel right though, as Windows would just mysteriously do things on its own and with no input from the user. Did you want a weather readout on your taskbar? We don't care, you're getting one there now, with links to Bing News! Random apps just showing up in Start, too. Things would just happen, without any action from the user. It--again--felt like we no longer owned our computers. Microsoft did.
But now, here in 2024, we've gotten used to 10's hubris, and arguably 10's going to look pretty damn good by the end of this because Microsoft further walked this path with Windows 11, an OS that does more of what 10 did before it was tamed properly, and arbitrarily dropped a whole host of hardware that could very much run it. For bonus points, Microsoft had the balls to announce all this right in the middle of a silicon shortage. So people who wanted to upgrade their PCs and even had the money to do so...couldn't. There was nothing to buy!
As if that wasn't enough, we also now have both companies doing AI garbage, though much like Windows 8's tablet UI, Microsoft is going all in on it and forcing it down everyone's gullet and even into innocent apps that haven't seen attention in decades, like Notepad. Yes, the AI bros are even coming for fuckin' NOTEPAD. What a world we live in.
This is why (and I'm sorry it took an eternity to arrive here) I think there's a lot of nostalgia and celebration around Windows 7 and Snow Leopard, and also why I think they deserve a seat at the table with the other retrocomputing thingamabobs: They're products from a bygone era. They were the last mainstream OSes from an age where it felt like technology was being made for the betterment of humankind, not just to exploit us for endless wads of cash.
They were from a time when we felt like we owned technology, not the other way around.
The dividing line between Windows 7/Snow Leopard and future releases feels--in hindsight--as significant as when Apple brought Steve Jobs back and there was a very clear line between the beige days of the mid 90s and the colorful translucence of the late 90s and early 00s. There was a massive vibe shift and I think as time goes on more and more of us are longing for the days before The Decline began.
I know I certainly am.