25 Fashion Trends of the Y2K Era

For every Sean Jean and Rocawear; there was an Akoo, Nostic, and Vokal. Throughout the 2000’s, if a rapper had a little bit of money and was willing to attach his name to a brand, he’d send out a clothing line. While most of these 2000s hip-hop fashion brands ended up at your local T.J. Maxx and A.J Wright (R.I.P.), this trend would evolve into some impressive, critically appreciated collections—like Andre 3000’s Benjamin Bixby. While rapper clothing lines have evolved into things like Kanye West’s Yeezy and Playboi Carti’s YVL, it’s safe to say that attempts at rapper-related clothing are mixed at best.

Sweatbands had bizarre crossover appeal. In hip-hop, they were like batters’ gloves in the '90s, a sports accessory that dudes started rocking in completely non-athletic contexts. In punk and emo circles, they had the same effect—ultimately becoming an accessory that was as ubiquitous as your local mall's Hot Topic. Today, they're relegated back to exclusive wear during the sports that inspired the trend, but we'll lament their role as the most athletic way to show you're unathletic.

Your sister's favorite boy band had them. Your auntie had them. A friend had them. For a minute, you definitely considered adding some extra light into your hairstyle. Sure, in retrospect, the style looked obnoxious at best (and like a skunk at worst), but back in the early-aughts it was the way to look like you hair was sun-kissed...whatever that means.

So cheap you could buy several for a dollar, but functional and simple enough to go with basically anything, the tall tee was one of hip-hop's most visible trends in the 2000s. It was also hit with controversy. Tall tees were banned in clubs, condemned in the press, and used as a tool to profile individuals. But at the end of the day, isn't it just a T-shirt that's four sizes too big?

When Ashton Kutcher, Britney Spears wore their Von Dutch trucker hats, they set off a headwear revolution. As the name implies, they get their name from the big rig drivers who wore (and were most likely given) the meshed hat on their long drives. It was one of the many “ironic” fashion staples of the decade, and something that would gradually fade out as the joke of dressing like Hank Hill or Fall Out Boy's Patrick Stump wore off. Fast forward to today, the trucker has had a full blown resurgence. Plenty of our favorite streetwear brands keep them in the rotation from season to season. No longer an ironic accessory choice, the trucker has become totally normalized.

Don’t lie, you had one of these on your wrist. If it wasn’t the iconic yellow, everyone had at least one of these rubber bracelets wrapped around their wrists during the last decade. Nothing made people feel like they’re making a difference to a well-known cause like copping a bracelet and wearing it everywhere. Either way, once anyone and everyone began making these for just about anything under the sun, they quickly faded out of favor (Lance Armstrong’s cheating revelations certainly didn’t help either).

Shouts to Bape (and the pursuing copycats) for this one. Aside from the full-zip hoodies, Bape and Billionaire Boys Club helped to front the all-over prints onto everything from T-shirts to hats. Generally involving a repeating icon or graphic, coupled with an arrangement of pastel colors, these are the types of pieces that made sure everyone knew your personal style from at least two miles away. Whether you were a fan of “Dipset Anthem,” or just were really into The Neptunes, it's more likely than not that you had something that was completely covered in print.

Yes, only the bravest of men would dive deep into the deep-V-neck game, but we'd be fronting if we didn't call out this as a trend. As retailers like American Apparel became more ubiquitous, the T-shirt crossed the country, overtaking the crewneck shirt as the de facto garb of hipsters and mall shoppers alike. While a V-neck's original purpose is to operate as undershirt, the piece quickly became as commonplace as the graphic tee of the 1990s. But by the end of the decade, there were more people making fun of the V-neck tee than there were people wearing it.

Straight out of the closets of John Legend-wannabes , this is a reminder that sometimes, you really can't dress down formalwear. A sign of someone who really couldn't make up their mind, it was a combination of the casual and formal. Mostly worn by dudes who looked like Common in the mid-00s, it's like dudes who wear denim, a sportscoat, and dress shoes. You end up looking like a dad at best or end up as the subject of a Kanye West rant at worst.

Geek chic is an invention of the 2000s. As traditionally nerdy pursuits and topics hit the mainstream (thanks Internet and rapid technological development), so did the desire of looking like Steve Urkel. The common move was to wear a bowtie with a J.Crew dress shirt tucked into jeans. Bonus points if suspenders made an appearance as well. As prep made a resurgence in the latter-half of the decade, dudes really thought they could make the look work in daily life. Sadly, with the rise of Sprezzatura roughly around the same time, most dudes just looked like professors at a southern university.

Remember how we talked on about the bizarre fusion of influences that created the “geek chic” trend? While the 2000s saw a rise in suburbanites shopping in thrift stores, it became ever more popular to dress like your grandpa. From the end of emo music's effect on the mainstream, into the rise of hipster culture at the end of the 2000s, cardigans made your grandparents one of the most relevant style icons. And don't lie, you know you wanted a Comme des Garçons PLAY cardigan with the heart.

The 1980s really were in full revival during the new millennium. What better way to pay homage to the decade than with a giant Casio or G-Shock? Maybe it had to do with all of the Flavor-Flav on VH1 during the decade, but the bigger the watch face the better when it came to your timepiece. Retro-meets-modern, and usually in a loud-as-hell colorway, these were the watches to rock if you didn't make a ton of cash, but still wanted to stunt.

Stemming from Kanye West's unstoppable album, Graduation, shutter shades became the de facto pointless accessory; someone would be caught wearing a pair in literally any and every public place—from senior prom, to the New Jersey boardwalk. Part of the ‘80s revival of the late 2000s, the shutter shades are actually a piece that came out of archives of eyewear designer Alain Mikli. Fortunately, due to the cyclical nature of fashion (or the fact that you genuinely cannot see where you're going wearing a pair of these), they faded out by the time Ye went into hiding post-2009 VMAs.

Airbrushed tees were a product of the '80s, but the 2000s drew inspiration from the street’s biggest artists. Brands like Ecko Unltd., Fubu, and PNB Nation all incorporated spraypaint and street art into their clothing in same fashion or another. Ecko even had his own branded video game centered around being a graffiti artist. Even Shepard Fairey's Obey made its mark near the end of decade thanks in part to his iconic “Hope” portrait of Barack Obama.

Mitchell & Ness made a killing outfitting dudes in retro jerseys and fitteds, reviving old school logos in such a big way that by the time Allen Iverson was dominating the NBA, it was nearly impossible not to see him without something retro related. Yes, the style became way too oversaturated way too quickly, but there's no denying its place in fashion history. With the help of Playboi Carti doing his finest Kriss Kross impression, this one has also seen a brief resurgence in modern hip-hop fashon.

We doubt that more dudes were wearing boots at the turn of the century, but for some reason, the bootcut jean saw an immense swell in availability in the 2000s. Bootcuts were fitted like a straight leg jean, but with a wider opening at the base. If you think of them like the menswear answer to the ladies’ “flare” jeans, then you wouldn't be too far off. While they do have their purpose—mainly to accommodate wearing high rise boots—the practical nature of straight leg jeans overrides the need for jeans with an OD leg opening.

While most well-dressed guys today compliment their footwear to their outfit, it’s safe to say that most dudes aren't making sure that their sneakers replicate the exact colors of their head-to-toe kit. Spurred on by more outlandish colorways and a burgeoning sneakerhead scene, guys wouldn't just hunt for classic colorways of their favorite sneakers on release day—they'd be buying sneakers to match clothes in their closet. Of course, this meant nothing if you didn't have the the hat to match.

Easily one of the biggest brands of the decade, American Apparel was the basics brand for everyone from parents to hipsters. Initially it was a pretty smart concept: provide shoppers with basics, and make it all ethically at a factory in L.A. It was a simple approach that was refreshing after the all-over print, color-saturated streetwear wave that came before it.

Perhaps it was the rise of pop-punk and the Vans Warped Tour in the middle of the decade that spawned these shaggy haircuts? Maybe it was the introduction of Justin Bieber back in 2008 that sealed the style into popular culture? Either way, the shaggy, bangs-heavy haircut became such a cultural icon in its own right, it was immortalized on Bieber's wax statue (inevitably, one of many). The style faded after Bieber himself cut his locks and adopted the undercut coif.

If your jeans weren't sunshine yellow or slime green, were you really wearing jeans in the 2000s? Everyone from backpack rappers to indie rockers had at least one pair of jeans that were anything but a shade of indigo. It's not as if these skinnies were different than any pair you'd find on the street today, but thanks to the rise of raw denim and dad jeans (and the fall of acts like the New Boyz), people kept their pants away from the pastel color palette.

The choice of VH1 reality show stars and celebrity parents alike, these brands ran amok in the mid-aughts. You're likely familiar with the chief offenders; a combination of Ed Hardy, Affliction, and Xtreme Couture plastered their over-the-top tattoo inspired designs on nearly every D-list celeb from Hollywood to the Jersey Shore (literally). If a child star or ex-boy band/girl group were still clinging to relevancy, it's likely they would be doing so clad in one of these brands. Fast forward to the present, brands like Ed Hardy are back in the fold. This time, they are leaning into the younger generation with fresh partnerships like Ken Carson and NBA YoungBoy.

Well before class was for men and swag was for boys, fedoras had a much different reputation. Around the time fitteds were hitting peak popularity, the retro headwear was gracing the heads of dudes with a more classic style (along with R&B dudes). With the saturation of trashy trillbys at nearly every big box retailer, the classic style of the fedora was tarnished beyond foreseeable repair.

For all the love that backpacks have today, messenger bags were the motion back in the aughts. As fixie bike culture began to swell, the bag of choice for bike messengers everywhere came right with it. While their practicality has never shifted, the lack of people actually adopting bike messenger positions left people opting for the easier, more universal backpack instead.

You know when you see someone wearing a scarf in the summertime or inside a well-heated building? You can blame the 2000s for that one. Keffiyehs or circle scarves, there's little question that the rise of hipster culture is the genesis of this temperature defying trend. Like a necklace, the most common way to wear this style would be with a simple T-shirt and skinny jeans. We can blame Lil Wayne and Kanye West for making a bunch of people think that they could pull this one off back then. Thankfully, this one has stayed in the past, for now.