The 50 Greatest Streetwear T-Shirts of All Time

Jeff Staple has put together the 50 greatest streetwear T-shirts of all time, and it might surprise you.

Photo Removed
Complex Original

Blank pixel used during image takedowns

Photo Removed

As told to James Harris.

If anyone were to ever take on the daunting task of thoroughly documenting all the players and personalities that have enabled the world of streetwear to prosper in just a few decades, certain names would require a lot more ink than others. James Jebbia, Eric Brunetti, Bobby Hundreds, Nigo, and so many others have been instrumental in creating a global industry that has adapted to and thrived within changes in political climate, advances in technology, and survived all manner of fleeting trends. Another name that deserves authoritative status and multiple pages when telling the story of streetwear: Jeff Staple.

Jeff's knowledge of streetwear's past and present, and his participation in molding its future all afford him the title of expert, and when it comes to a Herculean task like cobbling together the 50 greatest streetwear T-shirts of all time, he's one of the few dudes who can be trusted to execute.

At his own admission, ranking from the fiftieth best to number one would be an impossible task. Instead, he chose 50 tees that either represent strokes of genius design, conveyed powerful messages that went beyond streetwear, and pieces that set new benchmarks for the entire game. Roughly chronologically ordered, the T-shirts he chose cover four distinct eras in streetwear's existence: Streetwear B.C.; The Wonder Years; The Streetwear Explosion; and Streetwear 2Day. Any historian will note that these distinctive periods do bleed into one another in terms of time, but the beauty is that these trace the ongoing evolution of streetwear, a genre that always blurred lines and never stuck to set definitions imposed by others.

You may have owned a few of these T-shirts. Others, you may be seeing for the first time. But with each one, Jeff Staple gave the reasoning why it's deserving to be called one of the greatest ever. Each one of them has a story, and each one was an integral part in the evolution of streetwear, and the legacy that it leaves in influencing future creations. These are The 50 Greatest Streetwear T-Shirts of All Time, as Told by Jeff Staple.

RELATED: The 50 Greatest Streetwear Brands
RELATED: The 40 Best Streetwear Brands of the 2000s 
RELATED: The 10 Best Online Shops for Streetwear Clothing
RELATED: Green Label - The 10 Best Streetwear Brands Right Now

PNB Nation "89 Tec9 Stretch and Bobbito"

Photo Removed

Rawkus Records "Black Star"

Photo Removed

Milkcrate "Illson"

Photo Removed

Stussy "Logo"

Photo Removed

PNB Nation "Intention and Deed"

Photo Removed

Wu-Tang "Logo"

Photo Removed

PNB Nation "My Name Is"

Photo Removed

Project Dragon "Subway"

Photo Removed

PNB Nation "Uptown Dons"

Photo Removed

Milkcrate Athletics "OG Crate Logo"

Photo Removed

Triple Five Soul "Brooklyn"

Photo Removed

PNB Nation "Don't Test"

Photo Removed

Fuct "Logo"

Photo Removed

Obey "Andre The Giant"

Photo Removed

PNB Nation "Proud Nubian Brothers"

Photo Removed

Phat Farm "Logo"

Photo Removed

Supreme "Box Logo"

Photo Removed

Charizmatik "Listen to Your Heart"

Photo Removed

Irak "I Heart NY"

Photo Removed

Double Down "SixTrain"

Photo Removed

SSUR "Rebel Ape"

Photo Removed

Fuct "Jaws"

Photo Removed

Staple "Chinatown Gun Shop"

Photo Removed

Bape "Camo"

Photo Removed

Supeme "Astronaut"

Photo Removed

W)Taps "Tiger Stripe"

Photo Removed

Absurd "Ewing Twin Towers"

Photo Removed

aNYthing "Post 9-11"

Photo Removed

Supreme "Dipset"

Photo Removed

aNYthing "Logo"

Photo Removed

Rogue Status "Gun Show"

Photo Removed

Staple "Pigeon"

Photo Removed

King Stampede "Dashiki"

Photo Removed

Hundreds "Hip Hop is Dead"

Photo Removed

Huf "Etch a Sketch"

Photo Removed

Undefeated "Hardwood"

Photo Removed

Mighty Healthy "Mad People In New York Are Hustlers"

Photo Removed

Diamond Supply Co. "Iron Maiden"

Photo Removed

Nom De Guerre "Arabic"

Photo Removed

Comme Des Garcons Play "Heart"

Photo Removed

Opening Ceremony "LETTERS by Aurel Schmidt"

Photo Removed

UNDRCRWN "Bedstuy Bandit"

Photo Removed

Nike Gyakusou "Running Monks"

Photo Removed

Rocksmith "Notorious 81"

Photo Removed

No Mas "Strawberry"

Photo Removed

Stussy x Neckface "World Tour"

Photo Removed

SSUR/The Cut "COMME des FUCKDOWN"

Photo Removed

Reason "Go Love Your Own City"

Photo Removed

Rocksmith x UNDRCRWN "Keep Bouncin'"

Photo Removed

Supreme "Hanes Tagless"

Photo Removed

Latest in Style