Was 2016 the last good year?
A look back at the sneakers, clothes, and the cultural moments that shaped the future we know today
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Was 2016 the last good year? A lot of people on the internet seem to think so right now. Resharing fit pics, clothes, sneakers, and cultural moments that went down in 2016 seems to be the latest craze on social media.
Nostalgia is a topic that will never not be popular, and when a trend like resharing your fits from 2016 happens online, I usually tend to brush it off and go on about my life. But as I continued scrolling I started noticing references from 2016 that I was really obsessed with, so naturally, I did my own deep dive to remember what went down 10 years ago.
Besides dressing poorly in 2016, I’ve realized that maybe this was a time that’s actually worth getting nostalgic over—we were at a different point in fashion and culture that led us where we are today. In a way, dressing poorly in general was a step we needed to take in order to evolve as a society. It was a different time of trying that didn’t feel as performative as it does now, and that’s something I miss about clothing and culture in general.
It’s not just the clothing though. The cultural moments, new music, films, runways, and stuff in between that occured in 2016 all have earned their right to be called iconic.
I wanted to set the mood right, so I’m currently writing this while listening to Kanye West’s, The Life of Pablo, which released in 2016. We also can’t forget about projects like Blonde by Frank Ocean, Views by Drake, Jeffery by Young Thug, and ShremmLife2 by Rae Sremmurd that also released that same year—we were eating musically!
But we also had to say our goodbyes to legends like Prince, Leonard Cohen, and David Bowie that had passed away in 2016.
A lot of stuff went down that year, and while I won’t be able to highlight everything I want, today’s letter is a revisit to some of the most important culture moments, clothing and sneakers releases that helped define 2016, and how these moments influenced the future we live in today.
THE FOOTWEAR THAT SHAPED US
If you didn’t go through the era of trying to find the perfect tech pants to match with your Adidas NMDs, you simply weren’t outside. I don’t make the rules.
The NMD was instrumental in creating the sneaker hype culture. Online WDYWT threads online were flooded with fit pics that included the NMD. People were even talking about how this might have been the greatest Adidas shoe of all time.
The shoe space that year was actually crazy. Was it the peak of sneaker hype? I’m not at liberty to say, but I think we can’t deny that sneakers were at a different level back then. What do you think?
The Pharrell Human Race NMD was another huge moment that absolutely took the sneakerheads by storm. It was also a massive partnership for Adidas as they continued to build on their hype.
Then we had the Adidas Ultraboost 3.0 that released in December. Now I know that these had some initial steam a year prior, but the 3.0 was definitely a big deal. Originally debuting in 11 colorways—what’s up with shoe drops not being like that anymore? Now it’s always; here’s a collab with the new model first, and if that’s successful then you’ll get a thousand random releases to the point of exhaustion.
Anyway, the Ultraboost 3.0 was simply a must have shoe that every hypebeast had at some point in their lives, and if you didn’t, I’m afraid you were also not outside.
Speaking of footwear, although the idea of StockX started in March of 2025, it officially launched to the public in 2016. The platform would go on to completely reshape the reselling community forever. Crazy.
HE WAS HIM
None of the adidas footwear would have popped off the way they did if it wasn’t for Kanye though. This was his era, whatever he stepped out in that’s what the people would want to wear. It was simple as that.
Was 2016 the peak for him? That’s what some people say but I’m not going to get into that. I think we can all agree his influence during this period was massive for music and fashion.
But for fun, let’s take a look at some of Kanye’s big moments in 2016:
Debuted Yeezy Season 3 and Waves, what would actually go on to become The Life of Pablo album at Madison Square Garden. A massive cultural moment in music and fashion in general. It also brought us classic moments like, “Hold up, Thug wanna play some new sh*t” - 48:51 timestamp.
He debuted the Yeezy 350 v2 at that same Yeezy show at MSG that would go on to change the sneaker game forever. I mean come on. Do I even need to say anything else here?
The Life of Pablo tour ignited the Pablo merch that would go on to become an iconic collectors item for hypebeasts everywhere. Of course we can’t forget that this was the same tour he unfortunately got hospitalized in due to unpredictable outbursts mixed with Kim Kardashian’s robbery in Paris. It was a lot.
He also gave us this iconic photo of him that is still used as a meme template today.
Kim Kardashian leaked a part of the conversation between Kanye and Taylor Swift which would go on to become an instant-classic video where Kanye tells Taylor that he’s going to mention her in his upcoming track, Famous.
Was responsible in making the bomber jacket popular in the US in 2016.
and of course, we can’t forget the range of street style photos he had produced that continue to be the blueprint for style today.
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THE CLOTHES
Brands like Supreme were at the top of the hypebeast pyramid. Box logo anything was flying from the shelves. Lineups for every drop with popular items selling out online in seconds. Some say FW16 was Supreme’s best season, but honestly they say that about every collection.
Just like anything trendy, there were specific items that would stand above the rest that would get you put into respective sub genres of fashion—in this case it was being called a hypebeast.
Remember A$AP Rocky’s Guess collection that dropped those stripe shirts that everyone suddenly wanted? Or what about the insanely popular yellow Off-White industrial belt? What about those VLONE hoodies that you either hated or loved? Yeah, all of that went dropped in 2016.
At the same time the high fashion business was booming in its own way. Brands like Vetements won the International Urban Luxury Brand at the 2016 Fashion Awards, Gucci’s Alessandro Michele won International Accessories Designer of the year, Craig Green won British Menswear Designer of the Year, while Simone Rocha won the Womenswear Designer award. Demna won International Ready-to-Wear Designer for Balenciaga, and the Outstanding Achievement in Fashion was awarded to our GOAT, Ralph Lauren. Things were good!
Brands like VFILES were not only becoming a hub that would kickstart careers for designers like Virgil Abloh and Shayne Oliver, but also redefine what fashion and streetwear culture could become. RIP VFILES!
The VFiles Season 7 show that happened in September 2016 will forever go down as one of the most iconic moments in New York Fashion Week history—Young Thug, who was a mentor for the collection, famously got on the runway to fix a models collar in the middle of the show and then continued taking photos of the event on his iPad. Season 7 also featured the dress that Thugger used for the cover of the Jeffery mixtape.
While many would say that 2016 was rooted in cringe—I’m looking at those who have participated in the Mannequin Challenge, or sang along to Carpool Karaoke—these were the necessary steps we needed to take as a society to further develop our taste. Although I’m not sure if those moments helped or not, but we can definitely agree that taste has a completely different meaning today, and I’m not entirely sure whether were better off now than we were in 2016.
Personally, I don’t think we’re far enough away from 2016 to be THIS nostalgic over it. Most stuff still looks pretty ugly from this distance. That being said, in itself, it’s an interesting phenomena that the nostalgia cycles are getting shorter. This seems like something we should be looking back on in 2031, not 2026, but it’s been wild to see it seemingly organically take off all over social media.