The 100 Best T-Shirts of the 2000s (2024)

This feature was originally published on October 12, 2009

A t-shirt is just a t-shirt, right? Wrong. Especially wrong if you've been around this niche little industry we call streetwear. The past decade saw a rise in independent street fashion labels cranking out t-shirts with meanings, homages and dope graphics that became instant classics. We've even seem some brands who we thought would be around forever close up shop. Trust, a lot has gone on. Continuing with our Best Of The 2000s series, we now turn to the 100 Best T-Shirts of the last decade (2000-2009). Expect to see some you lined up for, as well as some under-the-radar shirts that you probably slept on. Let the madness begin...

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100. Young Jeezy "Snowman"

Released: 2005

When Jeezy burst onto the rap scene, he rocked these co*ke-friendly t-shirts guerilla style, but the USDA/CTE staples soon found themselves in mall stores and heavily bootlegged on the streets. They caused a stir and were eventually banned after young kids (and newscasters) caught on to the whole snowman = cocaine dealer thing. The shirts are nowhere to be found now, but as Mr. 17.5 himself said, you can't ban the snowman.

YOU AUGHTA KNOW:
Young Jeezy got his first Complex cover just this month. Yeahhhhhh.

99. Knights Of The Vampire Killers

Released: 2005

The Bushwick, NYC-based brand became a fashion darling for its imagined biker-gang backstory and faux-dirty motorcycle chic—not to mention a co-sign from David Bowie—but f*ck all that for a sec. Sometimes, success is as simple as a cool tee with bats and skulls flying on it.

YOU AUGHTA KNOW:
This t-shirt was hand-printed by Sean Reveron (who later launched RockersNYC) and was big in Japan. While rappers were rocking other labels, KOTVK received a co-sign from David Bowie.

98. SLB "puss* Stretcher"

Released: 2007

Remember Sal Barbier, pro skateboarder extraordinaire from the heyday of 1990s shred-tasticism? Oh, you were born in the ’90s? Ah. Anyway, he started his own clothing line an shop in LA a few years back, and this is one of the great T shirts from the racks. It has something to do with cats.

YOU AUGHTA KNOW:
Sal Barbier's etnies "23" sneaker was re-retroed from the '90s two years ago, and continues to be a big seller.

97. Reason "Go Love Your Own City"

Released: 2006

You know the "I Love New York Tee" every tourist and out-of-towner cops when they visit the Big Apple? The dudes behind Reason gave them a big eff-you when they released this t-shirt. Although Reason has had some classics (Diplomats), no design had more legs than this one.

YOU AUGHTA KNOW:
Just last month (September 2009), Reason collaborated with New Era on a "Go Love Your Own City" fitted.

96. Rocksmith x UNDRCRWN "Keep Bouncin"

Released: 2008

Rocksmith and Undercrown came together on this collabo shirt, and managed to homage A Tribe Called Quest and Michael Jordan at the same time. Tribe's Midnight Marauderdesign is sprawled all over MJ, and Rocksmith sought out Undercrown because of the brand's knack for pumping out sick basketball graphics.

YOU AUGHTA KNOW:
The image of Michael Jordan is from the 1988 slam dunk contest, which he won while wearing the Air Jordan III.

95. K-Swiss "Quiet Please"

Released: 2008

When the umpire at a tennis match needs to tell the crowd to shut it up, this is the saying most commonly uttered. The T-Shirt succeeds because it works just as effectively in the workplace/beach.

YOU AUGHTA KNOW:
K-Swiss sponsors tennis hot-stuff Ana Kournikova, who would still be all over everyone's walls if that damn Maria Sharapova hadn't turned up.

94. Acapulco Gold "Spit"

Released: 2007

If you can't skeet on somebody's lady, the best way to show disdain for them is to spit in their face (the dude, not their lady). AG hocks a big fat one and lets fly on luxury brand Louis Vuitton (Gucci and Chanel got hit too). Kanye does not approve, fam!

YOU AUGHTA KNOW:
More recently, AG has spit on some of the banking institutions that caused the recession: AIG, Merrill Lynch, and Goldman Sachs. Money shot!

93. Mato "Field Events"

Released: 2002

The talented trio behind this NYC-based line experimented with allover prints, asymmetrical designs, and cut-and-sew pieces well before their streetwear peers. Then they gracefully bowed out. Are you listening, Brett Favre?

YOU AUGHTA KNOW:
The founders of Mato went on to work for Rocksmith (Kenshin Ichikawa), Reebok (Matt Ting), and Nike SB (Chiu Liu).

92. Freshjive "HIPSTERS"

Released: 2008

Sorry if this offends you, but that's what T-shirts are for. You've got to admit it's kind of funny though, right? Rick Klotz, the king. Twenty-some years and still going strong.

YOU AUGHTA KNOW:
Shemagh are not a new trend with Americans. Soldiers in Vietnam wore them during the Cold War, when overtures were made to the Middle East to avoid their falling into the Communist sphere. Who knew?

91. DQM "I am New York"

Released: 2004

Martin Scorsese's Gangs of New Yorkended up being kind of a hot mess, but its Bill "The Butcher" Cutting character inspired DQM to create a shirt that reflected its take-no-streetwear-prisoners ethos. To paraphrase Hov, Daniel Day-Lewis made it a hot character, DQM made it a hot tee.

YOU AUGHTA KNOW:
DQM founder Dave Ortiz began his career as team manager at Zoo York.

90. House 33 "Scraps"

Released: 2007

Internationally known as a cool-guy type foundry, House Industries launched their House 33 line as a design collaboration between UK and US artists using computer generated and commercial art techniques, and the result has been awesome.

YOU AUGHTA KNOW:
House 33 has done design collabos with artists such as Don Letts, Bounty Hunter, and George Cox, and has sold fonts to the Hannah Montana franchise. Get money!

89. Insight "Infinite T"

Released: 2009

A mirror image of a mirror image. Yeah, that's not confusing at all. Great for distracting people's attention away from your ugly mug.

YOU AUGHTA KNOW:
This Aussie brand has been around since the '80s, but only for a few years stateside. They make the best t-shirts out right now, so we couldn't really decide which one to go with.

88. Wood Wood "Rainbow"

Released: 2006

Wood Wood is a Copenhagen storefront-turned-label, and the design trio has since worked on projects with adidas, MHI, and Penfield. Turning that frown upside down.

YOU AUGHTA KNOW:
Wood Wood handled the design responsibilities for the 44th issue of Arkitip.

87. Original Fake "Apple"

Released: 2008

KAWS teased the graphic on this t-shirt weeks prior to releasing it on his website, which got the hype machine spinning out of control. Although the t-shirt is believed to draw on NYC for inspiration, it has nothing to do with the title of Lloyd Banks' first album.

YOU AUGHTA KNOW:
The hand you see holding the apple is that of KAWS' popular Companion figure.

86. Fiberops "Upskirt Aficionado"

Released: 2002

Alyasha Owerka-Moore, the man behind Fiberops (and this whole T-shirt thing), crafted this banger for his Fiberops label when it was still a Japan/Hawaii-only thing. It loosely references being really good at perving out on girls, or so it seems.

YOU AUGHTA KNOW:
Although he is credited with "starting streetwear," Owerka-Moore has never done an allover print. King.

85. Volcom "Remy Stratton featured FA"

Released: 2008

This Volcom t-shirt was shot by photographer Remy Stratton, and the graphic on the shirt is of one of the brand's pro riders, Jake Duncombe. Stratton asked Duncombe to walk in front of a fire while at a skate event in Ohio, and then snapped the skater with an old Minolta point-and-shoot film camera.

YOU AUGHTA KNOW:
Stratton joined Volcom in 1992 as a pro team rider and then eventually handled skate team/marketing duties. The inspiration for this shirt comes from Stratton being a self-admitted pyro.

84. KISER "Sunglasses Is A Must"

Released: 2006

The NYC-based brand collaborated with A-Trak for this allover-print representation of the DJ's favorite saying. Good thing it's not "Codpieces are a must."

YOU AUGHTA KNOW:
Kanye rocked the shirt on an episode of TRL. You can still cop it at Karmaloop—if you wear XXL.

83. Ecko "I Am The American Dream"

Released: 2006

What can you say? The big homie turned a marker and a dream into a giant house and a company in New York's Flatiron District. COME SEE US!

YOU AUGHTA KNOW:
In the early days Ecko was spelled Echo, and most of the t-shirts on this list were designed by people who have spent at least a little time in the company halls.

82. Passarella Death Squad "Les femmes se revoltent, Le tueur s'eveille"

Released: 2009

Graphics that tastefully mix sex appeal with pop culture themes and world cities such as New York, Paris, and London are responsible for the cult-like following of Passarella Death Squad t-shirts, which are made with imported fabrics from Tokyo. To the East, my brother, to the East...sissy!

YOU AUGHTA KNOW:
If you buy one of these shirts, be sure to go one size up—they're Euro.

81. 2K By Gingham/Pierre Huyghe & Philippe Parreno "No Ghost Just A Shell"

Released: 2000

In 1999, Artists Pierre Huyghe and Phillippe Parreno purchased a stock manga character named Annlee and started the ongoing "No Ghost Just a Shell" project, where they asked various artist friends to create works that featured the character, starting with this design.

YOU AUGHTA KNOW:
The name "No Ghost Just A Shell" is a play on the classic '90s anime/manga Ghost In The Shell.

80. Lakai "Lakai or Die"

Released: 2007

Them boys from Torrance added just the right note to make Paris Hilton cool again, however tangentially. The fact that people were clamoring for these in the Carlton Banks colorup just proves the point. Now the question "who's tried on Paris Hilton?" has even more answers.

YOU AUGHTA KNOW:
The image of Paris was originally shot in 2004 by Mark Seliger for the group Citizen Change's get out the vote campaign.

79. No Mas "Cassius Clay"

Released: 2004

When it comes to No Mas classics, nothing is more O.G than this t-shirt. The "Cassius Clay" was the first t-shirt the brand ever produced, is the whole reason the company started. When it first dropped, the shirt was unlicensed, but after No Mas hit up Ali's people, the shirt got the official stamp.

YOU AUGHTA KNOW:
The shirt is a replica of the tee Muhammed Ali (then named Cassius Clay) wore during training for his 1964 bout against Sonny Liston.

78. KCDC "Bless This Mess"

Released: 2008

Adam Squires blessed the venerated Brooklyn skate shop with a bit of middle-America to freak out all the transplanted Omahans in Williamsburg.

YOU AUGHTA KNOW:
Over the years, KCDC has been adamant about not revealing what its letters stand for, although we've heard "Kangaroos Can't Dance Cutely" is definitely not it.

77. Amongst Friends "Hemp"

Released: 2008

AF did their drugs series back in '08, and we copped the weed one 'cause we wanted to rep something we actually use and they didn't make an Exelon Patch model...that we can recall, at least.

YOU AUGHTA KNOW:
Amongst Friends team members got their streetwear start at King Stampede.

76. Maharishi x War Child "War Child"

Released: 2005

After getting their start with re-purposed military gear, Maharishi teamed with War Child, a charity helping children affected by war, to come up with a tee that was dope and for a dope cause.

YOU AUGHTA KNOW:
According to popular legend, Maharishi designer Hardy Blechman can levitate.

75. Verte "Hsu"

Released: 2009

"Effortlessly cool" about sums up Jerry Hsu's skating stee*z, and the same can be said about his T-shirt design for Verte: a snake's mouth opened to reveal a spider web. Or a shark chowing down on a Native American dream catcher. Depends on how hard you squint your eyes.

YOU AUGHTA KNOW:
YouTube "Hsu Bag of Suck" to see Jerry kill it.

74. Pegleg NYC "Skulls"

Released: 2005

One of the downtown NYC brand's first T-shirts, the graphic might look like it was Pac-Man-inspired, but the brand says they got inspiration from summer squash and flat backs. Yeah, we're not sure either.

YOU AUGHTA KNOW:
Last spring/summer, Pegleg did a capsule collection for Opening Ceremony.

73. AcQUIRED "Acquired Logo"

Released: 2005

AcQUIRED is the brainchild of people behind Freshness, and this shirt lived up to the standard that they're known and respected for. Simple two-tone colorway and upside-down tree logo = dope. Yu-Ming, what up!

YOU AUGHTA KNOW:
A-Trak rocked an AcQUIRED shirt in the "Almighty DJ" issue of URB (RIP).

72. Staple "Windows 95"

Released: 2002

Long before Mac vs. PC commercials, Staple knew how much Windows sucked. This was not a great seller at the time because Mac basically had .00001% market share back then. Y'all got Jobbed!

YOU AUGHTA KNOW:
Staple is re-releasing the tee this fall as part of a program with Urban Outfitters called The Staple Archives.

71. 2K By Gingham/Garland Lyn "Punk vs. Disco"

Released: 2008

Garland Lyn's design works two ways: it flips the played-out skull icon to symbolize the death of sh*tty music! And to think it was just 30 years too late for Disco Demolition Nightat Comiskey.

YOU AUGHTA KNOW:
Lyn is an accomplished artist and designer, but we're fondest of those p*rny-ass Supreme ads he did. Or maybe his design partner. Either way. (Unbelievably NSFW)

70. Proof 7 "Proof"

Released: 2007

Proof 7 founders Laurence and Josh are NYC hustlers who have an event planning company and premium print business. It's hard out here for a print, but these guys nailed this graphic tee.

YOU AUGHTA KNOW:
In addition to Proof7, these guys have a fashion label called Rochambeau.

69. adidas "Ilie Nastase"

Released: 2006

Nastase, nicknamed the Bucharest Buffoon, was a true tennis G of the ’70s, back when players were allowed to have personalities. This Originals tee captures an Ilie bird flip—or maybe a demonstration of his finger-blast technique?

YOU AUGHTA KNOW:
Nastase was rumored to have slept with 2,500 women. Smash!

68. LOLA "Repeat Logo"

Released: 2007

NYC based brand LOLA went the repetition route with this logo tee, and cranked it out in several different colorways for the summer of 2007. If you were partying in the Hamptons, you probably saw the cool guys rockin' this design.

YOU AUGHTA KNOW:
LOLA got its name from Lola Prentice Memorial Park in the Hamptons, which was abandoned until cultivated into a skate park by 12- and 13-year-olds. It was destroyed later by police to "stop the kids from having too much fun."

67. F*cking Awesome "Metal"

Released: 2006

There are a lot of Misfits takedowns, but there is only one Misfits/Ozzie/Kiss takedown. Genius.

YOU AUGHTA KNOW:
The Misfits (and the Misfits logo) are the greatest thing to come out of New Jersey since... well, since ever. Sorry, Joey.

66. Lemar and Dauley "Spread Love It's the Brooklyn Way"

Released: 2007

Those all-over print-shirts aside, Lemar and Dauley tend to find the right balance of flash and class with their garment graphics. This Biggie memorial tee was no different. Adorned with stars, you get the Notorious one drapped in his pendant of choice: The Jesus piece. It's the Brooklyn way.

YOU AUGHTA KNOW:
The graphic was so popular, Lemar and Dauley used it for everything from hoodies and crewnecks to jackets.

65. Clientele "Mike"

Released: 2005

This Jumpman-esque all-over-print T-shirt came from the super exclusive gray-market sneaker hustlers at Clientele, and defined the early days of the brand MIKE.

YOU AUGHTA KNOW:
Flight Club now slings G-Shocks and 'Lo life out of the former Clientele location.

64. Clarendon "Bootleg"

Released: 2003

Clarendon was the label of Lizzie Grubman pal Jonathan Cheban, although the line's awesomely awesome designs were not to blame for Grubman running down a bunch of white trash in 2001.

YOU AUGHTA KNOW:
The 1st Earl of Clarendon, Edward Hyde, was grandfather to both Queen Mary II and Queen Anne.

63. Schwipe "Don't Come"

Released: 2007

Want a good way to promote your new gallery opening? Design a sick T-shirt for a popular streetwear brand bearing the title of the exhibition. That's exactly what Australian artist/skateboarder Stefan Marx did with this "Don't Come Underground" t-shirt for Schwipe. Marx had his "Don't Come" gallery opening in Australia around the same time.

YOU AUGHTA KNOW:
Schwipe stopped production on its line in early 2009. R.I.P.

62. Santos "F*ck This"

Released: 2008

Not all parties are created equal, which this tee clearly states. In fact, wearing this little gem communicates nothing so well as "f*ck this daily morning meeting, I'm hungover."

YOU AUGHTA KNOW:
Santos was originally slotted to be named "Santa's Party House," but the name was changed due to creative differences between investors. This club is located in Soho on Lafayette and puts together a real nice party.

61. The Hundreds "California Lifestyle"

Released: 2005

A tee from The Hundreds' early days, before the brand went hyper-mega-super global. All-black everything, who knew?

YOU AUGHTA KNOW:
The Hundreds name refers to the masses (as in people), not the Pilates drill.

60. Perks and Mini "Banana"

Released: 2005

The Melbourne-based brand known for its zany graphics "remastered" some of its old stuff in '09, including this shirt, which features a giant unpeeled banana. Damn, phallic much?

YOU AUGHTA KNOW:
Real-life couple Misha (PERKS) and Shauna (MINI) named their line after their graffiti names.

59. Wowch puss* Pistol

Released: 2006

Cats are way more hardbody than you think. You feed them, brush them, clean up their crap, and if you think twice about any of it, they'll merk you like a motherf*cking Civil War re-enactment. Say O HAI to the bad guy.

YOU AUGHTA KNOW:
Wowch caught a serious wedgie in '08 when a shirt they'd designed for Urban Outfitters in 2005 popped up—with the image flipped and the colors changed—on James Franco's character in Pineapple Express.

58. Mighty Healthy "Listen to Ghostface"

Released: 2006

DJ Denis Iderman and skater Ray Mate named their company after one of Ghostface's illest songs, so it's only right that the brand's breakthrough T-shirt pay tribute to Mr. Starks with a simple but effective command. Understand what we're sayin', sayin', sayin'?

YOU AUGHTA KNOW:
MH also went Wu for its Raekwon-inspired "Connect Politic Ditto" T-shirt.

57. Blood is the New Black "Annie Hollywood"

Released: 2008

Photographer Dan Monick's snap of Annie Hardy, lead singer-songwriter for Giant Drag (which isn't a drag queen band), pretty much encapsulates our thoughts on Hollywood. You go there with dreams and you end up gagging on something.

YOU AUGHTA KNOW:
One of Hardy's best known songs is "You f*ck Like My Dad." So he knows how to dick you down too, does he?

56. Union "Piece/Peace"

Released: 2006

Union proprietor Chris Gibbs went on a little Arabian kick and churned out this takedown off of a double entendre for the Spring/Summer '06 season.

YOU AUGHTA KNOW:
In Islam, it is considered sacrilege to draw images. Writing words in shapes is the backdoor trick around that little problem.

55. Nossa "Che Biggie"

Released: 2005

If any rapper was to be compared to Che Guevarra, we'd go with Tupac Shakur, but Nossa seemed to think Biggie was more befitting of the comparison. The Che-on-a-T-shirt thing has been played for a minute now, but this imagery is too striking to ignore, kinda like Biggie himself.

YOU AUGHTA KNOW:
This Brazilian streetwear brand is more recently known for its Latin political messages, like their new Pablo Escobar "Los Pepes" tee.

54. ALIFE "KR Logo"

Released: 2005

ALIFE's collab with Craig Costello (a.k.a. Krink a.k.a. KR) dropped when the company launched its Vancouver store. Krikey, it's dope.

YOU AUGHTA KNOW:
KR contributed his drip style to our 2008 Style & Design issue.

53. Pegleg NYC "Olde E"

Released: 2006

The dudes known for bold block colors started out with this early all-over print that reminds us of ye good olde days—when script was proper and English, and all our alcoholic beverages were charcoal- filtered with the strength of a tiger.

YOU AUGHTA KNOW:
Harry McNally, who started the brand with friends Nick Poe and Robert Waltzer, is the son of successful NYC restaurateur Keith McNally, the man responsible for Balthazar, Pastis, and Lucky Strike.

52. Twelve Bar "Heart"

Released: 2008

When your company's motto is "It's All Love" you better have a cool logo behind the saying. Mission accomplished for Twelve Bar. The heart-shaped graphic was the brand's bread and butter for every seasonal drop. When this hit the now-defunct online streetwear shop Digital Gravel, it sold out with the quickness.

YOU AUGHTA KNOW:
Twelve Bar has delved into the blogging game at http://www.twelvebar.com/astorytotell

51. Supreme "Dipset Boxed Photo"

Released: 2007

The first boxed logo photo tee featured Raekwon in 2006, and the Diplomats tee was produced a year later. Since then all, of the boxed logo tees have been overwhelmingly popular, creating lines down the block (Tera, Tyson, Kermit, and Lou Reed).

YOU AUGHTA KNOW:
Finding this shirt (or any other of this type) after they're sold out is a huge pain in the ass because hypebeasts run the prices up like crazy on eBay. f*ckers.

50. Union "Dilla Donuts Release Party"

Released: 2006

Coincidentally, Union cranked out this Dilla Donuts tee for a release party the store hosted two nights before the legendary producer passed away. After Dilla's death, the shirt became an immediate collectible.

YOU AUGHTA KNOW:
Union also did another Dilla tribute T-shirt and donated all the proceeds to his family.

49. PLAY Comme des Garçons "PLAY"

Released: 2007

Leave it to the elite Japanese brand to make a bug-eyed heart the epitome of cool for the "you ain't up on this" set. sh*t looks kinda creepy to us, but love is love.

YOU AUGHTA KNOW:
Including PLAY, Comme des Garçons has over 25 spin-off lines.

48. Destroy Your Enemy "Skull Headdress"

Released: 2002

This T-shirt was designed by Taka Hayashi before he started to cash the big bucks from Vans. Simple as that.

YOU AUGHTA KNOW:
Taka is known for several big projects, always incorporating elements of Americana and motorcycle art.

47. U.A.R.M. x FAILE "Shepard"

Released: 2005

The BK art collective's famous FAILE Dog finally made it off the wall and onto a shirt when the collaboration-mad kids at UARM got on the horn. Real talk, German Shepards make us crap our pants, but the shirt is still heat. FAILE is a win!

YOU AUGHTA KNOW:
UARM's collab track record features such no-names as R. Crumb, Neckface, the Basquiat estate, REAS, Ryan McGinness, and others. Not too f*cking shabby.

46. Brendan Donnelly "Narwhal Owl"

Released: 2004

Brendan Donnelly is one of those illustrator/designers who you call up if your T-shirt company starts sucking and he'll help pull you up by your boot-straps with some sick illustrations. The googly-eye narwhal owl was a little something he cooked up for his own label and sold to hipsters out of his one-season Ludlow St. popup.

YOU AUGHTA KNOW:
Brendan's newest line is a series of Arabic concert tees. Oh, and his blog is awesome: thebrendandonnelly.blogspot.com

45. Supreme "Joy Division"

Released: 2005

Supreme stays winning because it does things the right way. Instead of stealing this Joy Division graphic, the NYC label hit up Peter Saville to officially re-interpret his imagery on decks and T-shirts.

YOU AUGHTA KNOW:
Saville is known for his work with Joy Division and New Order, and recently did a snowboard outerwear series with DC.

44. SSUR "F*ck the Police/Synchronicity"

Released: 2000

SSUR flipped the Police album cover into something more appropriate, depending on who you are.

YOU AUGHTA KNOW:
N.W.A.'s f*ck tha Police originally released in 1988. What a long strange trip it's been.

43. Absurd "Ewing"

Released: 2004

Absurd designer Angelo Baque founded the brand in 2002 and cooked up a hometown classic by creating this image of Knicks great Patrick Ewing with his arm around the twin towers.

YOU AUGHTA KNOW:
Patrick Ewing is now the assistant coach of the Orlando Magic.

42. aNYthing "aNYthing Logo"

Released: 2002

A-ron's first logo dates back to the origins of his brand, but this T-shirt was an A New York Thing staple for years.

YOU AUGHTA KNOW:
A-Ron left aNYthing in 2007/2008 to start "Off Bowery".

41. J$ "Money"

Released: 2004

When all-over print was 'in" everyone was still out for dead presidents to represent them. Consider this the T-shirt version of rappers making it rain.

YOU AUGHTA KNOW:
Was one of the first all-over prints produced back in 2004, and was the original all-over money tee (ripoffs be damned). Founder Jamie Story's homie Thomas came up with the original concept.

40. St. Alfred "St Alfred YSL Logo"

Released: 2006

Chicago's premier streetwear/sneaker shop (which was created by steetwear visionary Ian Ginoza) has kept industry trendsetters like Lupe Fiasco and Kanye West laced for years. When the store decided to do a take off on YSL's signature initials, they brought it forward.

YOU AUGHTA KNOW:
The back of the tee reads "HI"—a shout to Ginoza's Hawaiian location, Kicks/HI.

39. Reason "Diplomats"

Released: 2004

Native NYCers Jon Totaro and Philip Bassis put their brand on the map with this shirt, a Dipset takeover of the Ramones' classic logo. sh*t's gonna be hella big at all those "2000's" parties five years from now.

YOU AUGHTA KNOW:
To create the original Ramones logo, artist Arturo Vega flipped the U.S. Presidential seal.

38. Crooks & Castles "High Society"

Released: 2005

Streetwear brands often try to take the piss out of high-fashion brands in their designs, and often put up a brick. Not the case with this Crooks tee.

YOU AUGHTA KNOW:
The paparazzi shutterbugs caught Jay-Z on the street rockin' this tee, which heavily increased the demand for the T-shirt months after it dropped.

37. Original Fake "Warm Regards"

Released: 2009

This KAWS piece is, literally, the sh*t. "Warm Regards" was originally produced as a mural for Aaron Rose's Beautiful Losers show at the Orange County Museum in Newport Beach, CA, and the T-shirt lets you become part of the action.

YOU AUGHTA KNOW:
KAWS also produced a vinyl "ice cream" Warm Regards poo stick. Haha, we said "poo."

36. Freshjive "Don't Tread On Me"

Released: 2008

The classic Cali brand demanded liberty or death with this summer T-shirt that resurrected the Gadsen Flag, a symbol of resistance dating back to the Revolutionary War.

YOU AUGHTA KNOW:
Lil Wayne famously rocked Freshjive's matching "Don't Tread On Me" fitted hat in the "A Milli" video. With some red skorts, or whatever the f*ck those were.

35. Lemar and Dauley "Back Like 45"

Released: 2006

The NYC nostalgia kings scored in the summer of '06 with this Jordan tribute tee that features the brand's signature stars and gradient design, originally released in three colors.

YOU AUGHTA KNOW:
The picture of Jordan's hand was taken from a 1999 advertising campaign for the Jordan XV, where MJ had his index finger up against his temple.

34. No Mas "Strawberry"

Released: 2005

No Mas always had fun cranking out designs inspired by the sports world, but Chris Isenberg and crew didn't even try to check their swing when they dropped this classic. The Straw and Nancy Reagan's infamous phrase are like two ironically juxtaposed peas in a pod.

YOU AUGHTA KNOW:
Nothing's better than real life—the shirt was inspired by a wristband Strawberry actually wore back in the late '80s.

33. Invisible:Man "p*rn"

Released: 2002

Naked girls on T-shirts seems as simple as 1+1 these days, but according to Mr. Lee, this is the first real "streetwear" tee to feature a big ol' p*rno booty. We say that respectfully, of course.

YOU AUGHTA KNOW:
Originally released at the Invisible:Man Tokyo store, this T shirt sold out in mere hours.

32. Plain Gravy "Pharrell Can't Skate"

Released: 2006

Los Angeles skaters jokingly struck back at hip-hop's sudden infatuation with their beloved sport by rocking this memorable comment about the one and only Skateboard P. The Ice Cream skate team struck back with their own tee: Pharrell CAN Skate. Take that!

YOU AUGHTA KNOW:
In 2008, a "Hiroshi can't fixed" takedown of this tee released.

31. Supreme x Neighborhood "Rebel Without a Pause"

Released: 2007

Supreme's first collaboration with Japanese brand Neighborhood sent shivers up the spine of the limited-edition mindspace. This T-shirt did not trigger the apocalypse (thankfully), but it did make for a pretty long line down the street.

YOU AUGHTA KNOW:
Supreme went on to do several collaborations with Neighborhood and some triple label sneakers with Vans.

30. Nom de Guerre "Woods"

Released: 2005

If there's one thing we can all agree on, it's that trees are Mother Nature's greatest gift to man. You know, because they produce oxygen and make for super-fresh script. Get your mind out the gravity bong, bro.

YOU AUGHTA KNOW:
NDG is known for not trying to be. The company's basem*nt shop is very difficult to find if you don't already know where you're going.

29. 10Deep "Problem Solvers"

Released: 2002

This t-shirt started as an inside joke pertaining to the use of violence to solve problems. The tee took off as people got the joke (or didn't), and the success of the shirt brought about many incarnations of the tee and led to the familiar brass knuckle becoming the logo for the brand.

YOU AUGHTA KNOW:
The brand eventually did a women's version of the T-shirt.

28. Orchard Street "International Baller: Bolivia 67"

Released: 2004

A favorite design of rappers like Nas and Puffy upon its original release, this particular camo colorway bore the phrase "Bolivia 67" on the back, a tribute to Che Guevara's death location and year.

YOU AUGHTA KNOW:
Orchard Street re-released the tee as part of their "Retro Pack II" in 2007.

27. Verte "Skull"

Released: 2007

All-over prints were just coming to an end and then Verte comes in with the BAM! Skulls/weed-leaf treasure chest.

YOU AUGHTA KNOW:
The shirt was designed by artist Arik Roper, a sick, sick illustrator who has done work for Nike, Rawkus Records, REAL Skateboards, Alien Workshop and the band High on Fire.

26. Diamond "Runnin' sh*t Since '98"

Released: 2005

Diamond Supply Co. head honcho Nick Tershay got inspired by Iron Maiden's Number of the Beastalbum cover, and re-interpreted the design into a skate/streetwear fan's wet dream.

YOU AUGHTA KNOW:
After the release of the shirt, Diamond was sued for $60k by Iron Maiden's licensing company

25. Mighty Healthy "Mad People in New York are Hustlers"

Released: 2005

T-shirts with messages are, for the most part, pretty lame. If you feel the need to walk around with some self-important proclamation on your chest, you should probably just get on Twitter ASAP. But this tee using magazine names and their typography is one of the most original, both in message and treatment.

YOU AUGHTA KNOW:
The guys behind Mighty Healthy don't just comment on the culture through their clothes, they also participate. Hit up their site for an awesome pirate radio station.

24. FALSE "Jumpin' Jolie"

Released: 2007

Singapore-based FALSE designer Le Messie enjoys paying no mind whatsoever to copyright laws. Here he gives us half Angelina Jolie, half superhero hands. Messie's designs back in the day were based on the breaking of bonds that tie one down.

YOU AUGHTA KNOW:
Amanda Scully and Le Messie are married—that's 2x the creative.

23. IRAK "I Rak NY"

Released: 2004

Ace Boon Kunle took the reigns of the NYC IRAK crew to the garment space, and made a statement on the classic NY tourist shirt that the big city was/is, in fact, his.

YOU AUGHTA KNOW:
The IRAK crew includes Aaron Bondaroff, Ryan McGinley, ESPO, and the late Dash Snow.

22. In4mation "Katie"

Released: 2006

For obvious reasons (namely the U.K.'s insane libel laws), this tee most certainly does not feature an image of one Kate "Katie" Moss. In fact, any resemblance is purely coincidental, and likely a result of your own out-of-control cocaine and rice cake habit.

YOU AUGHTA KNOW:
In4mation did another T-shirt that definitely did not feature a slightly altered image of supermodel Cindy Crawford.

21. FUCT x Vanguard "Sangue Italiano"

Released: 2009

Eric Brunetti might as well have invented the T-Shirt. With graphics like the JAWS takedown to the simple logo T, his brand killed it in the '90s, and it's back now doing its thing. This double label with Italian brand Vanguard says it all.

YOU AUGHTA KNOW:
The graphic for this T-shirt was drawn by hand and then transferred to the computer. Ah, the good old days of craftsmanship.

20. Crooks & Castles "Medusa"

Released: 2007

Is this the first Crooks tee? No. Is it the most iconic? Maybe, but it's definitely the dopest. Roman iconography mixed up with a red and green bandanna can't really be beat.

YOU AUGHTA KNOW:
Jay-Z was an early supporter of Crooks and helped launch the West Coast brand on the international stage.

19. 5BORO "Cinco Barrios"

Released: 2005

Designed by NYC artist Grotesk upon returning from a trip to Mexico, this is one of the most popular 5BORO skateboards and has been in the line for the last four years.

YOU AUGHTA KNOW:
The shirt has been appeared in It's Always Sunny in Philadelphia as well as Transformers 2. Suck it, LeBouef!

18. ALIFE "Wu-Tang Logo"

Released: 2006

ALIFE has held down New York's Lower East side for over a decade, and has had ties to the Wu for almost as long.

YOU AUGHTA KNOW:
ALIFE has hosted a series of backyard concerts with Raekwon and Ghostface at its Rivington Street location.

17. aNYthing "Juice"

Released: 2003

One of A-Ron the Don's early T-shirt designs, this is a takedown of Orenthal James's Buffalo jersey. Bills, bills, bills.

YOU AUGHTA KNOW:
O.J. appeared in the Naked Gun movie series before he turned into a complete asshole.

16. Rockers NYC "Peace = Haight"

Released: 2007

Inspired by 1970s peace posters and Amoeba Records art, this shirt falls right in line with the Rockers' dread philosophy. And look at that, tie-dye is coming back in for spring 2010. If you had hopped on this one, you would have been way ahead of the curve.

YOU AUGHTA KNOW:
Historians place the birth of tie-dye somewhere in the realm of 5000 years ago.

15. King Stampede "Lauren"

Released: 2006

Always coming with the unexpected, King Stampede showed another side of the city by flipping this infamous quote from old-school model Lauren Hutton about her motivations for first coming to NYC in 1964.

YOU AUGHTA KNOW:
LSD wasn't banned in the United States until October 1968.

14. UNDFTD "Le Tour"

Released: 2007

Right when the whole fixed-gear bike thing got really moving, UNDFTD crashed in with this puppy. Sick design, logos and all.

YOU AUGHTA KNOW:
There is a brand in South Korea, officially licensed as "UNDFTD," which bears the same logo as the California shop. It has nothing to do with the American version.

13. Rockwell "Rustico the Great"

Released: 2006

The Dutch artist Parra has made a lot of dope shirts with his brand Rockwell, but this winner from their 2006 Le Collection Noir is the only one that features a man who walks around with his feet inside vagin*s. We had never seen anything like this before, and probably never will again. Oh wait, you can just type "foot in vagin*" into Google images? Hold on...oh, GROSS.

YOU AUGHTA KNOW:
Rockwell brought back Rustico for a sequel in 2007's "Fade To Grey" collection, only this time our wayward hero was promoted to placing his hands inside vagin*s. Movin' on up!

12. BBC "Classic Arched" Logo

Released: 2005

With rappers' clothing lines disappearing faster than Twista spits, Pharrell's joint label with Nigo still does numbers. And the shirt that all started it? This simple helmet boy logo tee that's been remixed and ripped off over the years, but still attracts line-ups when they drop at the flagship stores. Seriously, if one released tomorrow, there'd be a whole bunch of kids lining up for one. As logos go, this guy has staying power.

YOU AUGHTA KNOW:
Everyone from Kanye to Lil Wayne to Clipse to Jermaine Dupri has worn the logo tee in their lifetime.

11. Maiden Noir "Midnight Sky"

Released: 2007

If Bret from Flight of the Conchordsgot a record deal, he'd trade up his swap-meet shirts for the standout tee from MN's Fall 2007 collection. Not too much animal, not too much pattern. This one is so dope, we wouldn't have been surprised if we'd seen Michael Vick rocking one of these dogs.

YOU AUGHTA KNOW:
The Seattle-based brand, originally famous for its skulls, has drawn on its regional surroundings to incorporate more and more wildlife iconography. Translation: they like nature!

10. Plain Gravy "It's So Easy"

Released: 2006

Inspired by Guns 'N' Roses' 1991 hit song "November Rain," which talks about the elusive and intangible nature of youth and fame, L.A.-based clothing brand Plain Gravy pays homage with this tee featuring an image of a young Axl Rose with the text "Nothing Lasts Forever" underneath. Nothing except the song's video, maybe. That sh*t was looooooooong.

YOU AUGHTA KNOW:
After being labeled hom*ophobic and racist due to lyrics from the G'N'R' song "One in a Million," Axl performed "November Rain" with Elton John at the 1992 MTV Video Music awards. And you thought Eminem was original.

9. AWOL/Rogue Status "Gun Show"

Released: 2006

They shootin'! The shirt first dropped back in ’06, was popularized by Rob Dyrdek on his MTV whizbang, and has adorned everything from bandannas to snowboard jackets since.

YOU AUGHTA KNOW:
The brand's founders—Jo Esbensen, Jasper Watts, and Rex Hollway—were all UNDFTD guys, then Dyrdek and Travis Barker signed on with a new name (Rogue Status) and joined the the journey to the graphic stratosphere.

8. Staple "Gun Shop"

Released: 2000

Staple's office at the time was across the street from Jim Jovino's Gun Shop, the oldest gun shop in NYC, and a spot that has served NY's Finest since 1911. This was a collab…of sorts.

YOU AUGHTA KNOW:
The name of the shop is done in Chinese because both houses were based in Chinatown and both proprietors are Chinese. There are a ton of limited-run colors in this style. Who's got Sky Blue with Chocolate Brown?!

7. Bathing Ape "BAPE Camo"

Released: 2005

The straightforward Bape camo tee is still better than every shot at something better. Hopefully the founder Nigo and crew will put this in the series of 2009 re-releases going down this season.

YOU AUGHTA KNOW:
Nigo means "number two" in Japanese. Get it? Number two? Sigh.

6. F*cking Awesome "Gangster Situations"

Released: 2005

f*cking Awesome is the brainchild of skateboarder Jason Dill and photographer Mike Piscitelli. The entire FA lineup could take up a bulk of the list, but we were forced to cut it down to a few of our favorites. Lagerfeld is king.

YOU AUGHTA KNOW:
You can still buy this shirt today on the FA site.

5. SSUR "Ne Blatuy"

Released: 2005

Some designers have their one "money" shirt, others do this sh*t in their sleep. Ruslan Karablin, one of the latter, keeps it tight with this classic.

YOU AUGHTA KNOW:
It roughly translates to "no snitchin'."

4. Stüssy "HAZE World Tour"

Released: 2006

For the year-long celebration of its World Tour T-Shirt (originally launched in 1989), Stüssy hit up over 40 artists to re-design the classic. From KAWS to GHOST to Futura and Neckface, there seemed to be a new one dropping every month. When the smoke cleared, this clean hand-style version by HAZE was, and continues to be, our favorite.

YOU AUGHTA KNOW:
HAZE is a graf legend, and was the designer who penned the Public Enemy logo.

3. Invisible:Man "Think"

Released: 2000

A much more subtle way of telling people to go kill themselves, wouldn't you say? Born in the day when Apple was a little upstart (who knew it would get to be where it is today?), this tee is a collector's item for original NY T-shirt kids and Japanese crazies alike.

YOU AUGHTA KNOW:
The T-shirt was inspired by Inspired the Apple billboard designer on 9th Avenue that Andrew Lee "saw everyday going to my sh*t job."

2. J$ "King of NY"

Released: 2003

Initially produced as a collaboration with filmmaker Joe Chan. No two seasons of King of NY are alike, due to different printing processes and colorups.

YOU AUGHTA KNOW:
The original idea for the company logo was just a money sign ($). Jamie Story realized that if he added a J before it, then it would also be his initials. So he figured, "Why the hell not?"

1. Supreme "Kate Moss"

Released: 2004

This Supreme graphic originally stems from the the street version—Supreme team members slapped shop stickers on the supermodel's Calvin Klein ads. It was released for the shop's 10-year anniversary, and got the co-sign from Ms. Moss.

YOU AUGHTA KNOW:
Supreme did a second Kate Moss tee in 2007, this one an actual collab with the model amidst a sea of ripoffs.