Men’s 2000s fashion is a mash-up, a sum of all that came the decade before. Also, the start of the end of monoculture, this era helped change style forever.
On one hand, you had reality TV and paparazzi culture. On the other hand, pop stars were playing instruments again.
You also have the first generation of youth who’ll live most of their life with home internet. This meant exposure to different lifestyles and cultures, no matter how small the town they lived in.
This also meant that 2000s men’s fashion was mixed.
We were on the other side of late ‘90s futurism, so what comes after the future? Pop had triumphed over grunge, so what does this mean for rock? In the nascent Wild West of social media, celebrities and tastemakers bypassed their PR teams, connecting directly to their fans.
I turned 13 in September 2001. It’s interesting to see how the world I grew up in has had such a lasting impact on menswear.
Y2K Men’s Fashion: An Overview
Late ‘90s futurism was a product of ‘60s and ‘70s revivalism remixed with the anticipation of the coming millennium. And it was still a big thing in the year 2000. Frosted tips and silver and gold accents were common at the height of the boy band craze.
Then, post-futurism took hold. What happens after the future has arrived? The end of the world, of course. But since pop overtook grunge by the end of the ‘90s, the resulting aesthetic was more of a fun dystopian chic. This took several forms.
Military jackets, ripped jeans, distressed leather, repurposed accessories, and poppified rock elements were staples on MTV’s Total Request Live. And TRL, a music video countdown show, was the epicenter of youth culture.
In the same year Britney Spears danced with a snake on the VMAs, she wore a tube sock as a glove for the Super Bowl half-time show. Then, she and Justin Timberlake wore matching denim outfits at the AMAs.
Denim was everywhere. Y2K men’s fashion included ripped denim with tank tops and ties, with blazers, with tuxedo jackets, with anything, really. There were no rules at the end of the world.
David Beckham and Lenny Kravitz were rocking Mad Max metals and Blade Runner leathers. But, they were doing it in a clean fashion, almost gender-bendy at the time. That’s because grooming, moisturizing, and overall caring about how you look was back.
The birth of the metrosexual and the influence of Queer Eye culture was rampant.
Emo boys, the remanifestation of rock with a touch of skater and goth, even wore makeup. This scene’s biggest contribution? The infamous skinny jeans.
And as always, this would proliferate into youth culture. A more family-friendly version of the look came to be associated with the later boy bands of the era, such as the Jonas Brothers.
The Mish Mash of 2000s Fashion Trends Men’s
On the other side of the fit spectrum, the early to mid-aughts saw the full commercialization of hip hop culture. Eminem and 50 Cent, along with the Backstreet Boys, were climbing the TRL charts.
This meant men wore preppier styles in baggy fits, while hip-hop styles were infused with brand labels.
And on the other side of the metrosexual spectrum were the working-class aesthetics of rap rock and rap metal. Limp Bizkit and Korn also had a place in fun dystopia. Still, trucker hats would become a pervasive 2000s men’s fashion trend.
The end of the decade started with neo-prep via Gossip Girl, as ‘70s revivalism started to make way for ‘80s revivalism. There was also the continued interest in electronics as fashion. Colorful iPods were all the rage throughout, and the first iPhone came out in 2007.
As we approached the actual end of the decade, two things happened.
First, EDM left its illicit warehouse beginnings and entered the top 40 airwaves.
Second, there was a recession. You’d think this would result in a Gen-X-like cynicism. But, this generation grew up on the return of bubblegum pop.
They instead approached this with an “all we have is today, party through the tragedy” attitude.
After all, “Mr. Brightside” was arguably the theme of the decade.
Escapist fashion, which resembled the no-rules, almost drag-like ‘80s club kid style mixed with electronic aesthetics, would bring us into the 2010s. Sleaze and glam.
I argue you can draw a straight line from dark emo to The Killers to Lady Gaga and Ke$ha. For men, think a pre-spray-tan, pre-abs Calvin Harris in his fly eyes, and Johnny Depp on every red carpet in late 2009.
Early 2000s Fashion Men
The decade opened with a bit of an identity crisis, though that’s what made it kind of fun.
Preppies wanted to be edgy, so they wore baggy jeans and pastel polo shirts. Hip-hoppers wanted to be classy, so they incorporated sweater vests and high-end brand names into their outfits. Rappers like Cam’ron and Kanye West weren’t afraid of the color pink.
Fits were all over the place. A man might wear a tight-fitting t-shirt with loose-fit jeans. Of course, by 2010, it was all about skinny jeans.
The everyday guy probably wore a polo with a popped collar, baggy jeans, possibly a rip here or there, and skater shoes.
The ill-fitting suits from the ‘90s carried over for a bit, though they’d start to get cleaner-lined towards the middle of the decade.
In the 2000s, the suit came in almost every cut. There were wide and small lapels, double-breasted and single-breasted jackets, two or three buttons, and different waist placements.
By the end of the 2000s, slim suits became popular, a trend that would last up until the 2020s.
Casual 2000s Men’s Fashion
By the ‘90s, a T-shirt and jeans were officially classic. Once reserved for edgy guys or the working class, this was the first era in which men of all types could wear this combo.
In the 2000s, business and the internet became inextricably related. So, not only were young boys wearing this casual combination to school, but so were entrepreneurs. Even today, a T-shirt and jeans outfit is synonymous with the Silicon Valley tech professional.
Furthermore, since the aughts were all about layers and high-lows your accessories reflected your tribe.
Guys with emo style went for a darker palette and skinnier fits. They’d then accessorize with a studded belt and guy-liner.
The more pop-rock guy might wear a tie and Vans slip-ons. But wait, you might be thinking, there’s no collar on a T-shirt. Doesn’t matter. If you’re lucky, you might find a belt studded with guitar picks at your local Hot Topic.
If you were going to a high school dance, you might wear dark jeans with a T-shirt, then throw a pin-striped suit vest over it.
Remember, layers were all the rage. So, you might even throw on a tracksuit jacket over your T-shirt and jeans. You’d definitely top it off with a trucker hat. We’re not sure whether this came from the guys on The Hills or the tween celebs starting their own YouTube Channels.
The internet and reality TV birthed a new kind of celebrity, a sort of pre-influencer.
Whether you were running errands or going to a fancy nightclub, you’d be in your best pair of denim pants.
If you weren’t a jeans guy, you may have been a cargo pants guy. Workwear and military wear were popular. And since we were “dancin’ ‘till the world ends,” as Britney Spears sang, military garb came in fun, bright colors.
It was workwear meets rave culture.
Men’s Fashion in the 2000s: Key items
Again, 2000 fashion men were a mish mash. You could stick to one camp, such as emo, neo-prep, or brand-forward hip hop. Or, as most of the youth did at the time, you could mix them up.
Here’s a toolbox of all things 2000s:
- Baggy jeans at the beginning of the decade and skinny jeans towards the end
- Trucker hats, especially ones from Von Dutch
- Cargo pants
- High and low combinations. For example, a tank top with a pinstriped suit vest or cargo pants made of silk. This was the era that normalized suits with T-shirts. Cool guys often wore an open zip-up hoodie in between their suit jackets and dress shirts.
- Distressed denim. Faded jeans were popular throughout the decade. The introduction of Americana and Western wear may have been a counter to the frosty futurism of the late ‘90s and early aughts.
- Boot-cut jeans
- Bucket hats
- Statement scarves a la Johnny Depp
- Skater shoes. Osiris and Vans were popular brands.
- Unexpected brand logos. Imagine someone in an ill-fitting tank top, ripped jeans, a trucker hat, then a leather Louis Vuitton belt.
- Layers upon layers
- Sweatbands
- Graphic tees. These often had funny, curt, or edgy statements on them. To really lean into the aughts mentality, you might wear it with a suit jacket.
- Emo style
- Studded belts
- Men in pink shirts. Related to the graphic tee trend, Abercrombie & Fitch used to sell a shirt that read, “Real men wear pink.”
- Neo-prep. Inspired by ‘80s prep, this was a colorful but less neon version of Ivy League style that incorporated high fashion with traditional heritage brands.
- Pop meets punk, a mix of preppy, rocker, and goth elements. The band Green Day’s aughts era is a great example. Billie Joe Armstrong often wore a skinny tie, a short-sleeved black dress shirt, a studded belt, and skinny jeans.
- Tracksuits. Going with the high-low trend at the time, high-end brands like Dior even served up tracksuits during the 2000s
- Military wear
- Suits in all cuts, from ‘70s wide lapels to jean-like breaks to skinny all-black emo suits
Men’s Y2K Outfits
Here are some examples of outfits exemplifying 2000s mens fashion. Some are more everyday examples, and others show how celebrities influenced the youth. And since so much of the aughts is back today, some are even contemporary reinterpreations.
Conclusion: A Dark Optimism
When it comes to 2000s men’s fashion, it was basically just one big party.
Our anxiousness about a potential Y2K computer meltdown made way for anxiousness over an actual financial meltdown. All rules went out the window. The internet had monoculture holding on for dear life.
And today, it’s hard to shock people with fashion. Moreover, no one judges joyful expression through fashion, even in tough times.
We wouldn’t have gotten here if not for the end-of-the-world rave we threw during the aughts.
Questions? Comments? Let me know below!
