The 100 Best Style Trends of the 2000s

This feature was originally published on November 9, 2009

We're heading into the home stretch of our almighty Best of the 2000s series, and word to Vanessa Williams, we're saving some of the best for last. Don't take this to mean we're not thoroughly knowledgeable about the other subjects we've already covered, but if Complex are authorities on anything, it's men's style. We observe trends, we set trends, we hump trends, we dump trends, we aretrends. This is what we do!

Our comprehensive inventory of the 100 Best Style Trends of the 2000s covers the good (plaid, chambray shirts, workwear), the bad (trucker hats, grills, back-pocket detail), and the WTF-were-you-thinking (headbands, skulls, full-zip hoodies). If you wore it during the last decade, chances are it's on our list. So get to clicking...and hating.

White trash started it, Pharrell made it popular, Ashton Kutcher made it reallypopular, Von Douchebags killed it...and now streetwear brands (and Judah Friedlander) are resurrecting the trucker hat. Or trying to, anyway.

LEADERS OF THE PACK:
Von Dutch, Replay, Diesel

What started off as a simple fundraising idea for the Lance Armstrong Foundation became a global phenomenon by the end of 2004. Nike and Armstrong set their goal at $25 million, only to blow past it within months. The $1 yellow rubber bracelets have been seen on the wrists of everyone from politicians to rappers to frat boys, selling over 70 million to date. At least the total lameness of rocking one is for a good cause, yeah?

LEADERS OF THE PACK:
Nike, Lance Armstrong

Sweats have been a sportswear classic forever, but only recently have they been getting love from the non-athletic brands. We've said it before, we'll say it again: Who doesn't love some fuckin' sweatpants?

LEADERS OF THE PACK:
Billionaire Boys Club, Umbro by Kim Jones, Y-3

Oh, Luke Wilson and your little friend Wes Anderson. What hath thou brought upon the modern head? We like the skinny shoelace style on the coked-up ladies of Los Angeles, but on the men? It was cool when it started, but now it's just garbage.

LEADERS OF THE PACK:
American Apparel, adidas, Jordan

Believe it or not, there was a time when the whole skull-and-crossbones motif was actually cool. Before it was thrown on any department store brand looking to attract younger buyers, brands like Supreme and Maiden Noir tastefully incorporated them into their designs. It was fun while it lasted.

LEADERS OF THE PACK:
Lucien Pellat-Finet, Maiden Noir, Wings + Horns

From Japanese streetwear fiends to Ed Hardy-wearing rock stars, everyone has shown off their back pockets at some point over the decade. Using increasingly elaborate stitching patterns, companies turned this previously blank canvas (for men at least) into a new place to stamp their signature style. And an excuse to say, "Hey, check out my ass!"

LEADERS OF THE PACK:
Evisu, True Religion, Rock & Republic

A little of the punk-rock street cred of a mohawk, minus the need to shave your head. David Beckham brought the look to a larger audience at the 2002 World Cup, but it probably took a whole team of stylists to get him tousled just so; if you can pull it off without looking like you tried, you're set.

LEADERS OF THE PACK:
David Beckham, Adam Levine, Aaron Yoo

Whether you were rocking a rugby or a polo shirt, popping your collar was the ultimate way to stunt (and hide a hickey) in the 2000s. And not just for bratty private-school kids: Polo heads like Kanye West rocked several mulit-colored collars at once to look even more stunt-tastic. Taste the rainbow, bitches!

LEADERS OF THE PACK:
Canterbury of New Zealand, Rugby, Lacoste

True, rappers have had clothing lines since the '90s, but none of them made it to the Macy's and Bloomingdales realm until the 2000s, when brands like Sean John and Rocawear broke out of the retail ghetto. Sadly, Dipset T-shirts can still only be found on 125th.

LEADERS OF THE PACK:
Sean John, Rocawear, G-Unit

Seen Paul Wall lately? Wonder how that grill company is doing. One of the greatest trends of our time, right up there with the stupidly ginormous chain on the "great moments in conspicuous consumption" chart. The recession killed a lot, but we're going to miss the grill the most.

LEADERS OF THE PACK:
Paul Wall, Lil Jon, Lil Wayne, Kanye West

Kanye's Pastelle line never actually cracked, but Polos and pastel colors (two of his other fave things) certainly did. The muted, understated, Easter-rific colors have always been closely associated with preppies, and like that social set, these shirts didn't need to scream to let you know they were money.

LEADERS OF THE PACK:
Opening Ceremony, United Bamboo, Pegleg

It seems that tattoos have basically become like another accessory—'cept the fact, of course, that you can't just take them off at the end of the day. Good luck with those job interviews.

LEADERS OF THE PACK:
Lil Wayne, Mike Tyson, The Game, Allen Iverson, Travis Barker

Remember what happened for, oh, eight of the 10 years this decade? You had money, your people had money, we all had more money than we knew what do with. Why not spend it on oversized technicolor diamonds fashioned into your favorite cartoon character/corporate logo/catchphrase? There's no WAY you'll regret that when the economy craters (or the shit gets got) and you're left looking like a soulless buffoon.

LEADERS OF THE PACK:
Pharrell, Rick Ross, T-Pain

When George Gorrow designed the first pair of shutter shades for Ksubi and passed them along to Kanye West, we doubt he had any idea what he was in for. George kick-started a trend of idiocy on St. Marks, but there was also a second trend that he helped popularize—that of crazy, giant eyewear. And it's still going on today. Happy brunching!

LEADERS OF THE PACK:
Maison Martin Margiela, Ksubi, Dior, Kanye West

Everybody wants to be a rock star, but it's easier to co-opt the look than the heroin abuse. Hence the popularity of this pyramid-studded accessory, once a punk-rock favorite but now just another something to clip your Sidekick to. Joey Ramone is rolling in his grave.

LEADERS OF THE PACK:
Vans, Nixon, RVCA

As a fashion craze, Barack-mania came to represent conformity more than a political stance, but any statement gets diluted once it makes it to a T-shirt. Sorry, Ché: Our generation has a new darling of mass-produced iconography.

LEADERS OF THE PACK:
Obey, UNDRCRWN, Commonwealth x Stüssy, Rocksmith, mad bootleggers worldwide

Simple, sporty, and super-cheap, drawstring (a.k.a. "cinch") bags like the ones made by Nike and adidas were the way to carry your shit around and keep it casual. Because, you know, not everybody wants to drop $300 on a perforated patent-leather backpack that doubles as a recording studio.

LEADERS OF THE PACK:
Eastpak, Nike, adidas, Umbro

You can't bury your Aughts time capsule without throwing in these early-to-mid-Aughts communication essentials: the flip-top Timeport pager and the T-Mobile Sidekick. Sidekicks are still around, but a moment of silence for the two-way: Who could forget "beaming" a chick at a club or Just Blaze's ill ringtones? To think how high-tech that shit was back then makes us think we'll be chuckling at BlackBerry madness in about eight years.

LEADERS OF THE PACK:
Motorola, T-Mobile

Sometimes you just feel like disappearin'. The full zip-up is not exactly utilitarian (unless you match it with a Louis Vuitton white cane), but to fuck with people, it fully serves its purpose.

LEADERS OF THE PACK:
Lrg, BAPE, Billionaire Boys Club

Around the time streetwear reached critical mass, nothing defined the movement more than allover prints. Yeah, we're glad that our favorite brands have gotten all grown with it, but we kinda miss the days of wallpaper disguised as clothing.

LEADERS OF THE PACK:
Lrg, OriginalFake, Kid Robot, BAPE, Stüssy, MHI

Not every dude can wear pink and pull it off. Less is usually more, but back in '03 that was not the case. A lot of heads were thinking pink, with the daring ones actually going head to toe. We have to send a shout-out to Cam'ron for single-handedly making this trend acceptable for non-fancyboys. As if the pink fur coats (with matching hats) weren't enough, he had to go and get the pink Range Rover. Don't worry, that's a throwaway, homes.

LEADERS OF THE PACK:
Acne, Lacoste, Polo Ralph Lauren, Uniqlo, Cam'ron

While we feel sorry for anyone who didn't grow up with Legos, when we look back at the Aughts we'll think of them as fashion accessories instead of toys, thanks (or no thanks?) to downtown NYC twins Dee and Ricky. After they hustled their product onto proven trendsetters like Kanye West and Marc Jacobs, cool guys everywhere were literally wearing their heart (amongst other designs) on their sleeves.

LEADERS OF THE PACK:
Dee & Ricky, Marc Jacobs, Kanye West, Lego

Once the little white box hit critical mass (and before third-party headphone makers went nuts), those white earbuds were easily one of the most popular accessories of the decade, worn by people of all backgrounds. Unfortunately they also screamed "I have a $200 electronics gadget on my person!" to potential jackers. Come and get me!

LEADERS OF THE PACK:
Apple, Bose, Skull Candy

You have to tip your hat to the sneaker companies. Already wringing money out of consumers on new products, brands double-dipped by dropping re-releases of shoes we used to love. Genius. It was access to all the kicks you couldn't afford to cop when they were new. Well, as long as you didn't mind lines.

LEADERS OF THE PACK:
Jordan, adidas, Nike, Puma, Reebok

The functionality of clothing grew more and more important as our economy went to shit, so waxed-cotton items became a great get. With weatherproof versatility and a subtle but striking glow, waxed-cotton gear was not only useful, but timelessly fresh as well.

LEADERS OF THE PACK:
Barbour, Steven Alan, Unis, Kangol

It wasn't quite as dominant as the North Face bubble coat in the '90s, but the military-inspired snorkel coat was definitely a winter outerwear staple for most of the Aughts. We always did like furry hoods.

LEADERS OF THE PACK:
The North Face, Canada Goose, Eddie Bauer

From the hood to the...well, the hood, Champion sweatshirts and their ilk kept it gully for yet another decade. Equally suited to a Rocky-style workout or a classic bodega post-up, the fleecy wonders remained the perfect fall staple. Handwarmer pockets, understated but necessary logo, and big enough to accomodate a healthy East Coast sag.

LEADERS OF THE PACK:
Reigning Champ, Champion, Uniqlo, UNDFTD

When they first started poppin up, "green" brands were all the rage: good for the environment while allowing you to get away with looking semi-dirtbag-ish. Then the tech got a little better, and the term became generic, resulting in the originators refocusing things and toning down the overt activism. Now, you can get stuff that is good for the world without looking like a hippie. Yay trends. Keep it moving.

LEADERS OF THE PACK:
Loomstate, Edun, Rogan

Trenches, trenches, everywhere: From the short ones, to the expensive ones, to everything in between, the classic outerwear piece came back with a vengeance in the latter part of the decade in a bunch of non-stuffy variations. Thankfully, flashing people on subways didn't also come back into style.

LEADERS OF THE PACK:
Prada, Burberry, J. Lindeberg

When sneakers become cool and acceptable anywhere in the early 2000s, you knew there was going to be a fashion-haus backlash. While the sneakers at work/dinner/discothèque thing still has a ways to go before it disappears, hard bottoms are cool again. Rock some with jeans and you will be getting the pretty lady. Yesss, sir. Just buy wisely.

LEADERS OF THE PACK:
Rachel Comey, Opening Ceremony, Paul Smith

Tip your hat to another comeback piece, this time the dome-topper that was widely popular in the '40s and '50s. Fitteds may be the fedora of our generation, but we still got love for the old-school hat.

LEADERS OF THE PACK:
Still Life, Kangol, Eugenia Kim

These have been around as long as people have been warring, but the early 2000s saw an increase in civilians of all types rocking these. The color and designs have expanded beyond the standard black combat-issued, but the distinctive high-rise and thick soles remained the same.

LEADERS OF THE PACK:
Dr. Martens, John Varvatos, Palladium

Holy cool, Batman! Negative space was used brilliantly by brands like L-R-G, Comme des Garçons, and Creative Recreation in the perforation of leather shoes, clothing, and accessories to give pieces that extra visual and textural flair. For once, it was cool for your gear to have holes in it.

LEADERS OF THE PACK:
Creative Recreation, L-R-G, Baracuta

This classic punk and skate accessory was a staple of the '90s, but a new generation of emo bands and "rock star" rappers (JONES!) brought it back to the mainstream in a major way this decade. Ironically, chain wallets are actually easier to steal than regular ones, but that's beside the point. They're badass!

LEADERS OF THE PACK:
WeSC, Obey, Famous Stars & Straps

Getting away for the weekend, but don't want to lug the rolling suitcase around? Gotta rock the duffle. Kanye and Pharrell were (once again) at the forefront of flipping an old standby into something fresh for the new school. But don't get it twisted, only Taz pronounces it "doo-flay."

LEADERS OF THE PACK:
American Apparel, Gravis, Supreme, Louis Vuitton

This '80s and '90s prep/trucker staple hit again in the middle of this decade. Stylish and practical (light enough for summer nights, but layer-able for colder weather), they even can be doubled-up with denim bottoms—but please, for the love of Levi's, don't call 'em jean jackets.

LEADERS OF THE PACK:
Levi's, PRPS, Gap, G-Star

With the emergence of hard-bottom shoes, the classic patterned W-shape cap toe reappeared in many collections in the latter Aughts. The traditional country-club shoe has a wing-tip pattern that always lends an air of sophistication. No white socks with these, people.

LEADERS OF THE PACK:
Lanvin, Brooks Brothers Black Fleece, Florsheim by Duckie Brown, Barker Black

Super-premium selvage denim is still running, but the kids have gone in the opposite direction over the last few years by breaking out tight, candy-colored denim on the daily. Blue, black, and gray were bound to get old. You're a jerk!

LEADERS OF THE PACK:
KR3W, Insight, Kill City

The ear-flap hat was big in the latter Aughts, and not just for those who like busting shots at deer. Yep, Elmer Fudd was onto something back in the day—the hunting-style hat has the comfort and style of a fitted with the furry warmth of a wool beanie. Vewwy vewwy dope.

LEADERS OF THE PACK:
Crooks & Castles, Filson, Kangol, Amongst Friends, New Era

You're a lame if you treat everything in your closet like the limited-edition kicks that you're scared to get a scuff on. The mountain trend embraced the rugged with heavy-duty gear and shoes meant to hold you down on rocky terrain, but also dope enough to keep you fresh in the streets.

LEADERS OF THE PACK:
Filson, Orvis, Polo, Dave's Quality Meats

Oversized chains? We've been off that. After the ice-infested '90s, designers still catered to male jewelry needs, but cleaned the look up a little bit. Brands like Philip Crangi and and Rogues Gallery hit it big with smaller, minimalistic pieces that caught the attention of guys looking for something extra without coming off douche-y like Ryan from The O.C.

LEADERS OF THE PACK:
Giles & Brothers, Chrome Hearts, Paul Smith, Philip Crangi, Rogues Gallery

The fanny pack has become one of the most derided accessories in fashion history, but that didn't stop this more subtle waist storage system from popping off. An extension of the Gucci/LV craze of the last few years, celebrities like Chris Brown have been seen hanging these little luxury purses on their belt-loops. Maybe we should use the term "coin murse" instead?

LEADERS OF THE PACK:
Head Porter, Stüssy, Louis Vuitton

The toggle coat, also known as the duffle coat, was first worn by the British Navy and is now favored by style-forward people who want to stand out in a world ruled by buttons and zippers. It might take a little longer to close a toggle, but hey it's only freezing cold.

LEADERS OF THE PACK:
Filippa K., J. Lindeberg, Y-3, Richard Chai

Bicycle style owes everything to the pioneers of the trend: the messengers. The look—slim jackets for aerodynamics, skinny jeans to avoid chain grab, and low-pro sneaks to fit into toe-clips—was born as a creature of necessity. Trend-followers have pushed the style mainstream, but real fixies know who's really down.

LEADERS OF THE PACK:
Bianchi, Brooklyn Machine Works, Dave's Quality Meats

It wasn't too long ago that industry parties looked like athletic events and Mitchell & Ness was the preeminent outfitter of the rap world. Yeah, Jay-Z ethered the whole look, but it was fun while it lasted—as long as you don't have dozens of $350 M&N joints collecting dust in your closet.

LEADERS OF THE PACK:
Mitchell & Ness, Starter, Fabolous

When the Supra Skytop samples first showed up, everyone was like, "Oh Muska, you craazy ass." Next thing you know, fashion houses are going super-high, Hov is rocking 'em, and the rip-off train is coming choo-chooing down the track at Magic. All aboard!

LEADERS OF THE PACK:
Air Jordan, Generic Man, Pierre Hardy, Supra

Took dudes a while to run with these, then they started getting crazy. Let's just make this clear: Deep Vs (for men) are not cool. V-neck tees are worn by pretty much everybody and there are no signs of them slowing down any time soon. They've become the safe, casual "go-to-look," for better or worse.

LEADERS OF THE PACK:
American Apparel, Shades of Greige, Calvin Klein, Alternative Apparel

Honestly, when was flannel not in style? Proving that the Neil Young look will neither burn out nor fade away, plaid came back to the forefront of fashion late in the decade, and now kids everywhere rock fresh flannels with their Nike Blazers. Harvest!

LEADERS OF THE PACK:
The Hundreds, Ransom, Fresh Jive, Stüssy

Patent leather brings to mind tuxedos and military uniforms—i.e., class, but used in sneakers it was all about the flash. It's one of the few design features that can out-shout neon. Wear a lot or a little, depending upon how high you want to pump up the volume.

LEADERS OF THE PACK:
Common Projects, Supra, Nike

Chck chck boom! Who knew Cheney's legacy would be in the form of this fashion piece. Putting on one of these (and a hunting hat, another Aughts favorite) allowed for a free pass to drink beer and "accidentally" clip your friend.

LEADERS OF THE PACK:
Barbour, Maiden Noir, Burberry

Mixing the formal and the casual is nothing new, but the blazer-jeans combo really took off around 2003, providing schlubby men an instant way to add some class to their everyday steez. When did this look jump the shark? As soon as companies started making blazers with the hoodie actually built in. Just say no.

LEADERS OF THE PACK:
Gant, Cheap Monday, United Bamboo, Z Zegna

Go in! Hate the player, hate the game, hate the owners, hate the fans. Testing the limits of irony, frogskins were a ski-culture bastardization that hit big in the Aughts, scoring with the "let's dress so wack it's cool" crowd.

LEADERS OF THE PACK:
Oakley, KR3W, Mosley Tribes

We all know that what goes around comes back around (and around again), especially in the fashion world. The mod subculture is rightfully associated with 1960s London, but the look was too clean to be ignored in the 2000s. Simplicity is key with mod style, but the updated version was about more than just black and white.

LEADERS OF THE PACK:
April77, YMC, Marc by Marc Jacobs

Dunks for the hipsters, Jordans for the rappers, Uptowns for the proletariat—but the Air Max? Whether in the 1s, 90s, 95s, or 97s, the oft-retro'ed line had a little something for everybody in the Aughts.

LEADERS OF THE PACK:
Nike

These rainy-weather essentials got a style upgrade in the Aughts. The L.L. Bean joints were still classic, but more design-heavy versions became a cool-guy favorite. No matter the kind, these boots are perfect for jumping in puddles and fucking up other peoples' days. Splishy-splash!

LEADERS OF THE PACK:
L.L. Bean, Polo Ralph Lauren, Gourmet

It feels weird to admit that Marlon Brando can be credited with starting a trend that isn't "going crazy and moving to Tahiti," but after he rolled onscreen in The Wild One, it was a wrap. Leather and denim became an instant classic for anyone feeling rebellious, and the look caught a comeback this decade once the crotch-rocket bike trend faded. Simplicity, versatility, and comfort? Be easy, rider.

LEADERS OF THE PACK:
Neighborhood, W)TAPS, Obey x Levi's, Vans

The words "skateboarding" and "fashion" were never supposed to be synonymous, but as every other subculture was systematically hollowed out, skaters' simple, functional style became an easy mark. Soon rappers were wearing Nike SB and DC along with their Louis Vuitton and Gucci. The game hasn't been the same since.

LEADERS OF THE PACK:
KR3W, Vans, Volcom, Insight, Emerica, Altamont

The manbag had a slow start in the first part of the decade, but non-backpack carryalls—whether totes, duffles, or assorted shoulder-bags—soon became an accepted (and even prized) male accessory. Yours probably doesn't cost $67,000 like Pharrell's Hermès tote does, but you're probably nowhere near as rich as Skingraft P, either.

LEADERS OF THE PACK:
Louis Vuitton, Dunhill, Hugo Boss, Bottega Venetta, Porter

Shots fired! Jay-Z delivered the death blow to throwbacks in 2003 when he declared, "I don't wear jerseys, I'm 30-plus/give me a fresh pair of jeans and some button-ups." Then, of course, the sheep killed the whole button-ups/loose jeans look, too. Fortunately, basic oxford shirts are basically trend-proof.

LEADERS OF THE PACK:
Polo Ralph Lauren, J.Crew, Steven Alan

Fashion types always say that trends are a reflection of what's going on in the world. They're probably right, considering the way military-style clothing took off at the height of our conflict in Iraq. Thankfully, we never had to face enemy fire in our M65s and cargo pants, but the austere steez (and convenience of having so many pockets) made these a hit with the common man. And by the looks of the Afghanistan situation, this trend will probably stick around for a while.

LEADERS OF THE PACK:
Nom de Guerre, G-Star, Obey

Recession-shmissession. This was the decade in which denim prices skyrocketed, expensive "selvage" became king, and heads started caring about Japanese shuttle looms. Forget church, people found True Religion just by maxing out their credit cards. You've spent $300 bucks on a lot worse shit, that's for sure.

LEADERS OF THE PACK:
Diesel, G-Star, Evisu, PRPS

Unless you were a snowboarder, winter fashion usually focused more on function than style: Who cares if you look fly if you're freezing your ass off? But then companies like Moncler prettied up cold-weather outerwear by making fashionable jackets that didn't neglect the keep-you-warm part. Toasty!

LEADERS OF THE PACK:
Moncler, Penfield, The North Face

If the '80s was moustaches and the '90s was goatees, then the Aughts was the decade of the beard. Whether meticulously groomed (à la Rick Ross) or scruffily unkempt (à la white people), copious facial hair became a style standard. Unless you played for the Yankees.

LEADERS OF THE PACK:
Rick Ross, Terry Richardson, Russell Brand

Sunglass trends were all over the place this decade, but like a proper analog watch or a basic white tee, aviator shades stayed a constant in the "even-you-can't-fuck-this-one-up" category of style.

LEADERS OF THE PACK:
Ray-Ban, YSL, Louis Vuitton, Cazal, Mosley Tribes

Sneakers felt like they'd already peaked (this was before grown-man sneakers came along, when everyone was drowning in bright-ass splashes like the greedy geniuses they were), and hard-bottom shoes felt a little stuffy. So, if you think about it, the rise of the boat shoe was pretty much inevitable. With a more sophisticated silhouette, and enough color/pattern variety to satisfy the most voracious of hypebeasts, the summertime yacht bonanza crossed over to the skreets and became a phenomenon.

LEADERS OF THE PACK:
Sperry Top-Sider, Sebago, Vans, Band of Outsiders for Sperry

Digital, analog, sundial-style: Gold watches have been a go-to accessory for years. Flaunt it if you've got it, and if somebody trips, just smack 'em across the chin with your Rolex...or Swatch.

LEADERS OF THE PACK:
Rolex, I.W.C., Michael Kors, Swatch

Manservant chic was one thing, but once Fonzworth dropped the umbrella and joined forces with Andre 3000 to propagate the Bagger Vance x Andover aesthetic in earnest, heads actually started learning how to tie a bow tie and got dressed up from the chest up: Kanye, Skateboard P, Wale, even Chris Breezy took a swing at it. What, too soon?

LEADERS OF THE PACK:
Alexander Olch, Brooks Brothers Black Fleece, Gant

So you want a limited-edition piece? A fresh collabo? How about this for a one-of-one: [BRAND] x you. Corporations responded to the hypebeast explosion by allowing consumers to customize nearly every detail of their purchases, most notably with Nike's groundbreaking iD program. Great idea, but customizing gear is like cutting your own hair—cool if done right, but disastrous in the wrong hands. This means you.

LEADERS OF THE PACK:
NIKEiD, Vans, Reebok, Puma, Polo

Square?! Why, thank you! The pocket square hasn't really been popping since your granddaddy's heyday, but recently it's allowed young guys to have fun with the one suit they own, adding color and a bit of maturity. Not to mention it's pretty cool to pull out a square to mop the brows of everyone who's sweating you.

LEADERS OF THE PACK:
J.Crew, Jack Spade, J. Press, Paul Stuart

We just love it when a style from our youth—like, our youthyouth—makes a triumphant return. Such was the case with cuffed pants, a trend that rolled up outta nowhere in the late Aughts. Designers brought the look to the runways by working built-in cuffs and cuff-styling to their collections.

LEADERS OF THE PACK:
Dockers, YMC, Robert Geller, Rugby

Even if you don't summer in Nantucket, nautical style proved to be one of hottest looks of the Aughts. We're not just talking about boat shoes either. Navy blue blazers, striped sweaters, and ribbon belts were also necessary for those seeking to conjure up that seaman steez (no pause). And while naval-inspired gear looks great on the street, taking it to actual water every once in a while is must—blue-blooded or not.

LEADERS OF THE PACK:
Noah, Wings & Horns, Rogues Gallery, Norsea

Rocking a penguin suit inevitably results in a feeling of old-school conformity, but one way to retain a little edge in the Aughts was by wearing a slim cravat. That is, until everybody started rocking them, and you started feeling like Ryan Seacrest.

LEADERS OF THE PACK:
Band of Outsiders, Hugo Boss, Dior

They started as something to combat rainy weather and ended up being an outerwear essential no matter the conditions. Coming in many shapes, forms, and sizes, windbreakers were a favorite for both sportswear and streetwear brands to push forward their best tech x design ideas.

LEADERS OF THE PACK:
adidas SLVR, Y-3, Nike, MHI, Stüssy, Dior

The return of '80s style was always in the cards, but who knew that cats would go this hard? The Retro Kids were the most visible (and thorough) purveyors of the trend, but the movement kept movin' beyond hip-hop with the comeback of acid-wash jeans and classic surf brands. Now get your camouflage shit ready for the '90s retro movement...coming soon.

LEADERS OF THE PACK:
Maui & Sons, Insight, Quiksilver, Opening Ceremony, Fruition, The Retro Kids

The inevitable response to allover-kill was a return to keeping it simple, stupid. That meant ditching the logos for basics from American (or Alternative) Apparel, Uniqlo, and the good ol' Gap. Dressing for cheap without looking it, what's not to love?

LEADERS OF THE PACK:
American Apparel, Alternative Apparel, The Gap, Uniqlo

Once considered cheap, in the 2000s plastic watches became the fun, colorful, lightweight alternative to the serious metal timepieces your dad would wear. With brands like G-Shock, Nixon, and Timex doing all sorts of cool designer collaborations, hobos weren't the only ones collecting plastic.

LEADERS OF THE PACK:
G-Shock, Nixon, Nooka, Toy Watch

For so long, the streets popularized aspirational brands that fronted like they were too good for the hood. Then along came premium brands like A Bathing Ape and Ice Cream, which flaunted their affiliation with cut, color, and pattern choices, as well as relationships with rappers like Pharrell, Clipse, and Lil Wayne—and suddenly it was all good in the hood. (Until inferior biters got out of control, anyway.)

LEADERS OF THE PACK:
BAPE, Ice Cream, Billionaire Boys Club, Swagger, OriginalFake

The indomitable Uptowns were reborn in the Aughts with endless custom designs and all kinds of hand-painted fuckery. The more outlandish styles died out around the time throwbacks did, but it's safe to say that the 1s aren't going anywhere soon.

LEADERS OF THE PACK:
Nike

Why? Why the fuck not? In the decade when sneaker culture went from niche to nouveau riche, it was inevitable that top-shelf designers would get in on the craziness, too. Are we advocating buying a pair of $575 sneakers? Maybe not, but at least you know you can.

LEADERS OF THE PACK:
Common Porjects, Maison Martin Margiela, Dior, Lanvin, Rick Owens, Pierre Hardy

Black has always been the most versitile base color in fashion, but this decade, things got a little gray. Nowhere was this more evident than in the denim world, where gray became a cool alternative to blue and black—gray goes with everything, and still gives you a lower profile than brighter dyed denim.

LEADERS OF THE PACK:
Maiden Noir, Stüssy Deluxe, Dunderdon, WeSC

Call 'em plimsolls or call 'em tennis shoes, but the O.G. sneaker came back around for a reason. The perfect subtle complement for summer—whether with shorts, jeans, or khakis—trickled down from Vans and up from Chucks, and met somewhere in the very comfortable middle.

LEADERS OF THE PACK:
Aprix, Vans, DVS, Supreme, Keds

Sure, half the people wearing these specs didn't even need glasses, but we don't need vision correction to see that they were important for making geek chic. Put a pair of these on and you just look smart. And isn't that far better than kids thinking gunshot wounds are hot accessories?

LEADERS OF THE PACK:
Moscot, Oliver Peoples, Super

When it came down to it, black was the new black. Yeah, Jay-Z was on that but we didn't need Hov to know that blackening our wardrobe was an easy way to stay on trend without trying too hard. Matchy-matchy is easy when you're all murdered out.

LEADERS OF THE PACK:
Comme des Garçons, Yohji Yamamoto

Denim enthusiasts already knew raw selvage was the cream of the crop, but in the Aughts everybody became a fan of clean, sturdy seams made through old-school production techniques. Check ya cuffs!

LEADERS OF THE PACK:
Levi's, A.P.C., Kicking Mule, Uniqlo, Gilded Age

Sneaker trends came and went but good ol' rugged boots were never out of style during this decade. Construction Timbs remained a stalwart but the latter Aughts saw the reemergence of Red Wings as well as shit-kickin' collabos from other footwear companies. Working class, indeed.

LEADERS OF THE PACK:
Red Wing, Timberland, Vasque, Ransom for adidas

Some say that a certain college dropout made it cool to look like an Ivy Leaguer, but even after 'Ye moved on, the preppy steez continued to get high marks throughout the decade. Ralph Lauren launched Rugby, J.Crew got their shit together, and prepping up became the smart move.

LEADERS OF THE PACK:
Jack Spade, Gant, Brooks Brothers, Rugby, J.Crew

Great jackets have a combination of design, functionality, and durability, all features that have been staples of the M65 for decades. While brands in the 2000s reinvented the military-inspired jacket with more color options and modern fits, this type of coat have been around since—yup you guessed it—1965.

LEADERS OF THE PACK:
Obey, Polo Ralph Lauren, Maiden Noir, Stüssy, Nike

After money got big faces in the late '90s, you had to figure the things that money bought couldn't be far behind. And watches kept up their end of the bargain, with manufacturers trading in subtlety for chunky flair. Loud? Maybe, but at least your admirers will knew what time it was.

LEADERS OF THE PACK:
Bell & Ross, U-Boat, Hublot, Tsovet

Another military influence that held down the decade, the bomber jacket was available in a variety of different flavors, from easy rider to top gunner to city slickster—no matter what, though, it was always Fonz-cool.

LEADERS OF THE PACK:
Corpus, Public School, PRPS, Diesel, rag & bone

Terrorize anything lately? Arab leaders started this trend in order to promote acceptance and to disguise operatives who were walking around NYC. Kidding. Kind of.

LEADERS OF THE PACK:
A Peace Treaty, Nicholas K., PLO leaders

Independent footwear took a slice of the market-share pie from the big three/four this decade, taking the T-shirt upstart idea to a bigger forum. Instead of waiting for the shoe monoliths to entertain their ideas and supply them with what they wanted, savvy designers went ahead and made them themselves. More footwear choices from risk-taking companies = a big win for consumers.

LEADERS OF THE PACK:
Clae, Creative Recreation, Supra, Common Projects

People have been wearing graphic T-shirts forever, but in the Aughts, everybody (and their little brother) wanted to start their own T-shirt line. A lot of them sucked, but we can think of, oh, 100 T-shirts or so that we really liked.

LEADERS OF THE PACK:
aNYthing, FUCT, Supreme, OriginalFake

Lumberjack. Indie rocker. Preppie. Gangbanger. Surfer. Whatever your steez, traditional and tweaked plaids were the way to rep all your colors at once. Like Busta Rhymes, the 2000s got you all in check! WOO-HAH!!

LEADERS OF THE PACK:
Steven Alan, 10.Deep, HUF, Nom de Guerre

Denim's softer French cousin got a rebirth in the Aughts. The last few years have seen these rugged blue shirts popping up in the collections of many workwear-friendly designers.

LEADERS OF THE PACK:
J.Crew, Gant, 3sixteen, Steven Alan, Devilock, Levi's

If Mad Men has taught us anything, it's that you can get away with a lot of shit when you dress this nice. Smartening up in a tailored suit didn't mean you can drink, smoke, and fuck without consequence, but it sure made your vices a lot more appealing. Word to muthafuckin' Don Draper.

LEADERS OF THE PACK:
Dior, Boss Black, Ermenegildo Zegna, Calvin Klein

They're often known as "letterman" jackets, but in the Aughts, varsity jackets were for more than just the jock types. The classic patched-up look remained, but a host of designers cleaned up the look with more modern variations. Either way, you were still the B.M.O.C.

LEADERS OF THE PACK:
Nike, Supreme, L-R-G, Stüssy, Wings + Horns

To be fair, the fitted baseball cap would make the Top 100 Trends list for every decade before (or after) the Aughts, but the classic accessory had plenty of shine during this new era. In the earlier part of the decade, multicolored pinwheels popped off to complement the popularity of throwbacks, and by decade's end, streetwear teams turned out enough fitteds to rival their MLB counterparts.

LEADERS OF THE PACK:
New Era, Starter, Supreme, 10.Deep, HUF

It wasn't just footwear that experienced a revival of blue-collar style in the Aughts—the classic Americana aesthetic was promoted by workwear brands that produced dependable, durable clothes that were as resistant against fickle trends as they were against the elements. They made it easy work to look good.

LEADERS OF THE PACK:
Engineered Garments, Woolrich Woolen Mills, PRPS, Levi's, Ralph Lauren Double RL

Mr. Rogers' favorite piece came back to neighborhoods everywhere around the middle of the decade, and cardigan sweaters haven't left since. If we told you that 10 years ago, you'd probably go: "Yeah, and I'm sure hip-hop kids will be rocking skinny jeans, too." Uh...yeah.

LEADERS OF THE PACK:
Rogan. Tse, Vince, J.Lindeberg, Diesel

Much to the chagrin of '90s-era rappers, this decade's most notable trend sounded the death knell (in most circles) of baggy denim. A whole generation of dudes slimmed down to slim-fitting (and sometimes skinny) jeans—but unfortuately, most kids refused to wear them on their actual waists. The resulting "tight-sag" meant a lot of youngins were walking around like penguins. So here's a goal for the next decade: slim-fit jeans that actually fit.

LEADERS OF THE PACK:
Cheap Monday, A.P.C., Kill City, Altamont