Just imagine the amount of data the 2000s produced. Now, I’m not saying I went through all of it to get the top 2000s fashion for men trends you need to know about. But I have digested the nuances of the 2000s men’s fashion using both the memory of my childhood/teen era and exhaustive internet research. All for the good of the reader.

Confused as to what that decade might entail from a fashion perspective? Think shell necklaces, leather bracelets, striped T-Shirts, glow sticks, baggy jeans, spiky hair, rimless sunglasses, flip phones, fat skate shoes, wallet chains, geeky cardigans, indie music, ripped denim, fedoras, Pokemon, Nintendo DS, rave sunnies, piercings, mascara, Zoey Deschanel, Justin Timberlake, Alexa Chung, David Beckham, Brad Pitt, and on and on until 23:59:59, 2019.

The 2000s clothing trends are back, folks. If you want proof, just know the iconic Nike Vomero 5 relaunched at the end of last year, people are using Nikon Coolpix digital cameras, and baggy/bootcut jeans are in. What I’ve tried to do in outlining these trends is give you as many options for adopting these into your own style.

For entry into the cheapest and most fashionable time machine you’ll ever enter, read on.

Key Takeaways 

This style guide takes you through the only 2000s clothing trends for men worth knowing about in 2023. However, TL;DR, here’s a peak at a few products that are tickets onto the spaceship heading to the year 2000. Gramicci’s cargo pants have a very Y2K skater quality, slotting somewhere between Gorpcore and modern streetwear.

A colorblock fleece by 66°North is a must-have. For a casual and uplifting dose of double-denim, go for a jacket and jeans combination by Marni. And finally, a pair of rimless Meller shades will transport you straight to 2004.

Denim is good. It’s durable, chic, timeless, and casual. It can be dressed up or down. We all know denim is iconic. So double-denim is double-good, right? Well, hold onto your rivets because despite it being a beloved fabric of just about any era, the noughties really went in on men’s denim, often opting for an excess of material. There’s a lot to turn your nose up about the denim of that period, so let’s cherry-pick the best bits so you can build them into your arsenal of styles.

Let’s start with the downright daring: the boilersuit. There’s a 25% chance you can pull this off. But if you can, your style and kudos are instantly stratified. Wear it in the warmer months, roll up the ankles, and don white Air Force 1s (or other white sneakers). Is it double-denim? Technically it’s a one-piece, but it’s twice as much denim as one normally dares to wear, so you do the math.

Want a more smart-casual approach? Try a dark pair of denim with a light-wash chambray shirt. It’s a Canadian tuxedo that lives up to its formalwear allusions. Looking for the epitome of a modern interpretation of the 00s denim jeans and jacket trend? Marni’s double-denim ensemble has volume and good vibes aplenty. Maybe something more low-key and laidback? Haikure’s shacket and pants combo is just the ticket.

This combo is preppy squared. A marriage of preppy items that only the noughties could have ordained. I turned to Reddit for style advice on this one (not always recommended, but it proved fruitful here). Firstly, color matches between the polo and button-down shirt are advisable. This helps the slightly extravagant aesthetic seem less so.

Speaking of extravagance, one user pointed out the double collar’s closeness to an Ascot tie or cravat. I like the comparison, though clearly, on a casual scale. In terms of styling, the more buttons you undo, the more visible the polo becomes, the more noticeable and gregarious it becomes. One user vouched for its practicality since it protects the shirt from, and I quote, “neck grease.” (God, I feel queasy.)

The natural starting points for polo shirts are Abercrombie (a controversial sweetheart of 2000s fashion for men) and J Crew. You get vibrant and striped options while avoiding obvious branding. Closed also has no breast logo and a range of soft pastel hues perfect for the summer. In the collared button-down shirt department, stripes are obviously bolder than plain, so use that information how you please. For full-force noughties style, wear it with clashing jeans and a Fossil lava stone bracelet.

Historically, looser fits in menswear have prevailed. The tall tees of basketball and hip-hop were dominant in 2000s men’s clothing trends, particularly in the USA. H&M’s Brooklyn tee being a prime example.

Down below, of course, everything was baggy. Since most people were wearing denim, let’s check out the best baggy 2000s fashion for men trend-inspired denim going. Axel Arigato gives a very suave and very baggy counterpoint to the stonewash jeans loved at the time. Also big were ripped jeans, and Closed produces a faithful modern-day reimagining.

K-Pop mega group BTS, a band very much of this era, has delved into the boyband aesthetic of tracksuits. But if the full tracksuit just isn’t noughties enough for you, you can upgrade to velvet. Take a classic bottoms and hoodie combination by Pierre. You will look like a f*cking rockstar buying your milk and papers in this.

If the names LeBron James, Shaquille O’Neal, and Kobe Bryant mean anything to you, there’s a pitchside kit from Nike just waiting for you, paying homage to the Milwaukee Bucks. Which, if you’re from the UK and are not into basketball (guilty), means it’s just one of the best, non-controversial tracksuits.

Backstreet’s Back, alright? And so are cargo pants. Their military history means they’re rugged, camouflaged, and pragmatic. The original 2000s fashion for men brought it back with less military might and more RnB/boy band infusion. Baggy cargo pants are ideal for navigating both the current style and the practicality of daily life. In this sense, it’s a dream blend of Gorp and streetwear.

Stylistically, Gramicci is bang on the money. They’re loose, they come with a hang-down belt, they’re built for outdoor activities, and they come in a range of palatable colors. Corridor NYC provides a lightweight ripstop pair of pants in a pastel-olive hue. For a smart-casual, modern take, I wholeheartedly recommend Grant’s cargo trousers.

Style your cargo trousers with a long-sleeved tee by Magic Castles and some wonderful Oakley slip-on shoes for a futurist-retro Gorp look.

“And I wonder if you know… how it really feels… to be left outside alone… when it’s cold out here.” Yes, Anastacia’s 2004 released Left Outside Alone (what a music video) is the unofficial soundtrack to tinted sunglasses. She is the poster girl for that particular 2000s fashion trend. As for the lads, we have David Beckham, Justin Timberlake, and T.I. all failing to outdo Anastacia but all equally donning the style.

The Versace shades have an iconic 200s look about them—rimless, tinted, and a little bit bling. There was a brief moment where rimless technology really exploded (until Sven-Göran Eriksson got involved). Now, in the present day, Cartier has harnessed the best of sunglasses style. On the rimmed side of shades, Oakley brings a more sporting edge, while the 80s shutter rave sunnies are reliving their brief stint in the 00s.

The cheap 90s digital quartz watch boom continued into the 00s. The retro G-Shock, though born in the eighties, was still loved in the 00s. In particular, this little boy from The Midlands and his cherished bright yellow G-Shock and a metal cage protector.

New watches in the Y2K style are hard to come by. But Timex made a timepiece that imitates the bubbled aesthetic of 2000s fashion for men, and it’s an affordable entry point to the style. Plus, Nixon created a chunky masterpiece of their own if you’re up for a slightly higher price tag.

P.S. on the subject of tech, styling, and Y2K, get yourself a crappy digital camera; it looks kitsch and is objectively fun, so, what’s not to love? For other fun Y2K devices, see iPods, Nintendo DS, and the Motorola Razr.

Not Kurt Cobain’s fluffy mohair cardies, but the lightweight, cotton knitted cardigans of the 00s. Think Geek Chic and indie-sleaze. Think Arctic Monkeys, OK Go, Hot Chip, Vampire Weekend, Hot Hot Heat, Bombay Bicycle Club, etc.

Cardigans are kind of my jam, so forgive me while I try to narrow down an exhaustive list of the greatest cardigans in 2000s fashion for men. Ralph Lauren merges the plain lightweight feel of the 2000s men’s cardigan with preppy style.

For geek chic try Corridor NYC. For streetwear infusion, try Edwin Europe. For subtlety, try 3sixteen. When styling your new favorite cardigan, keep it minimal keeping it within grey, navy, or black for a smart-casual aesthetic. For a little more flair, give it a bit of verve and personality with patterns and a bit of color.

Once you’ve given your shaved head its dye pattern, why not extend that to a full outfit? All-over prints were huge in 2000s clothing trends. They’re out there, bright and gaudy. The best and worst of the era. Pharrell William’s brand Billionaire Boys Club is renowned for its all-over prints. Particularly their 2000s men’s fashion outfit combining both all-over prints and double-denim. Wax London has also designed the perfect all-over print for the summertime combining a short-sleeved shirt and lightweight pants.

Here’s a fun question for you. Which years did the TV show “O.C.” run? If you thought it was precisely 2003-2007, then you would be correct. This TV show came slap bang in the middle of the noughties and it is an important reflection of California preppy style mixed with commercial indie-rock.

There are a lot of mid-wash bootcut jeans because not to generalize or anything, but that’s what most people were wearing at the time. It makes for one of the best jeans styles thanks to the space they afford your footwear down below and its slightly janky aesthetic. For modern takes, start with G-Star RAW jeans and Levi’s 527s.

Trucker hats have decorated the freeways for decades. But also, celebrities like Lindsay Lohan, Ashton Kutcher, and Britney Spears were all caught donning the trucker cap. And if this all-star list of celebrities doesn’t point to the era in which they were prime, I don’t know what will. Miss Spears made the Von Dutch cap famous. So if you want to go straight to the source of the trend, go for the maximalist Von Dutch cap in a bright blue velour. If you didn’t almost puke reading that sentence, you probably will have seen it and fallen in love already.

For a more palatable and accessible approach to getting truckin’, Ililily’s cap embraces the dusty, industrial, well-worn side of the trucker cap aesthetic. With streetwear also emerging, the era of the snapback was only growing. This makes for a good alternative option to the trucker cap for the 00s-loving, cap-wearing among you.

Fashion endlessly “throws back.” Eventually, like a boomerang, the trend is going to hit you on the back of the head and be relevant again. Throwback jerseys, for example, focus on vintage sports jerseys (mainly baseball and basketball), like a  mesh basketball vest. They’ll look at home with a pair of baggy shorts, baggy jeans, tinted shades, or some loud jewelry. We hear throwback jerseys go really well with spinners and car hydraulics systems too.

Wow. I know this is a list of 2000s things, but this is really a 2000s fashion trend. There are three main streaky hair highlights. The first: tipped or frosted (cheers “older brother from Malcolm in The Middle”). Then there’s the most accurate, or literally streaky hairstyle, modeled perfectly by N Sync.

Finally, there’s the emo-tinge modeled by the one and only Pete Wentz (singer and bassist from Fall Out Boy) in a red/black contrast. At Barcelona airport recently, I saw a lady with horizontal, skunk-like streaks in a tortoiseshell colorway. It was jarring. And I respected it hugely. So, maybe streaks are back? It certainly aligns with the shaved hair dye patterns seen all over TikTok.

Fleece is super popular these days thanks to the rise of Gorpcore and the outdoor aesthetic. But in the 2000s, the boom of synthetic fabrics saw the fleece jacket become a mainstay due to its warmth, style, and accessibility.

Adsum’s fleece modernizes the 2000s fashion for men by constructing with 85% recycled polyester. The Percival fleece gives more of a retro feel than the 2000s men’s trend, but the noughties took inspiration from here and it’s too nice to leave out. And just in case you ever need to become an Icelandic sheep, 66 Degrees North is your go-to.

For styling, try to incorporate color blocking since fleeces often are blocked, and utilize oversized layering since it matches the general noughties’ need for bagginess.

The rugby player in me is disgusted that my sport has been reduced to something so meaningless as a trend. The fashion writer in me is giddy. The rugby shirt trend points to a decade dominated by rich, young American men who all wore terrible leather bracelets. However, its recent revival is something to cheer from the sidelines for.

Brands like Drake’s and Rowing Blazers have given the rugby shirt stylish vintage flair. For a little peep into where the rugby shirt is right now in the modern era, J Crew’s option brings a lot to the table.

Final Verdict 

To round off this 2000s men’s clothing article, I’m going to style my ideal outfit. Beginning with the easy-to-style Gramicci cargo pants. Next up, I’ll throw on a streetwear cardigan by Corridor. Then I’ll get myself a trucker cap and a funky digital watch. Vaguely street, vaguely preppy, mainly 2000s.