Two downtown legends, Stash and Futura are graffiti artists and kindred spirits who both got their start in the ‘80s graffiti and hip-hop boom. Although they briefly worked together when they launched their design collective Recon in 1998, the two eventually parted ways to open their own sneaker boutiques—Stash’s Nort 235 and Futura’s (also titled) Recon. In 2005, however, the two reconnected and opened their collaborative space appropriately named Nort/Recon on Lafayette Street.

Nort/Recon offered an expanded selection of sneakers as well as accessories, collectables and clothing, including its in-house apparel line Recon. The standout Recon piece was undoubtedly the “I Miss the Old New York” T-shirt which became a recurring graphic throughout the 2000s. Flipping the familiar New York Times typeface, the shirt was a reference to New York’s accelerated gentrification following policies put in place by then-mayor Rudy Giuliani. The shirt captured the tongue-in-cheek sense of humor that continues to be the basis for many streetwear designs to this day. Still relevant today, the “I Miss the Old New York” reappeared earlier this year when Richardson, as part of their collaboration with Highsnobiety Japan, reincorporated the classic logo into its own graphic T-shirt. Although Recon was discontinued nearly a decade ago, the T-shirt has had a lasting impact.

Nom de Guerre was a brand that defied convention. Launched October 2003, Nom de Guerre opened a retail location in NoHo which used to operate as a former Black Panthers hideout. The store was hidden down a flight of steps without any clear identifiable markings. Shoppers would descend into a cavernous space that contained a unique mix of products that ranged from graphic tees to workwear. Limited sneaker releases sat alongside the in-house collection with was described as "utilitarian luxury-basics.”

New York boasted plenty of other streetwear shops at the time, but Nom De Guerre stood out for its minimal aesthetic that catered to a more mature audience. The brand was not logo-heavy or graphic driven and chose to focus instead on garments that drew inspiration from classic military pieces and vintage workwear. With a debut collection featuring collaborations with Buzz Ricksons, Mackintosh, Converse, Russell Moccasin Company and Tricker's, Nome de Guerre was as diverse as it was ahead of its time.

While the brand sadly folded after its Fall/Winter 2010 collection, demand for Nom de Guerre continues to this day. In particular, the often-imitated but never rivaled paratrooper pant has developed something of a cult following. Modeled after an actual military design, the silhouette predated techwear and repurposed cargos by years. The garment—and Nom de Guerre in general—proved that, despite the label, streetwear could be much more than hoodies and graphic tees.

In 2002, Supreme already boasted an impressive following. With stores in New York and Japan, the then eight-year-old company was considered a symbol of downtown New York, however outside the world of streetwear was still relatively niche. Its first official collaboration with Nike changed all that. When Supreme started bringing Japan-exclusive co.jp Nike Dunks to its New York store in 2001, it proved there was a market for limited edition dunks in the states. A year later, as part of its Spring/Summer 2002 collection it launched its first collaborative Nike sneaker, the “Cement” SB Dunk Low. Inspired by the classic Jordan III, the sneaker helped put the then-fledgling Nike Skateboarding imprint on the map. At the time the cement print was exclusive to that Jordan retro and had never been seen on another shoe. Suddenly, the skate shoe was on every sneakerhead's wishlist.

Without a website at the time, news of the Supreme exclusive spread solely through blogs and word of mouth. The sneaker release garnered a huge amount of buzz on online sneaker community NikeTalk—then the preeminent internet hub for all things sneakers—and helped introduce the brand to a whole new audience. With rumored production numbers of just 750 black pairs and only 500 in white, demand obviously outweighed supply. To cultivate the buzz, Supreme dropped a small number of pairs each day at its stores in New York and Japan, which resulted in a week-long line that began early each morning, a scene that would became commonplace at all Supreme locations in the years to come. After the release, suddenly sneaker blogs began discussing Supreme, setting the stage for the brand's eventual global recognition.

Aaron “A-Ron” Bondaroff first made a name for himself working at Supreme. Store manager as well as de-facto public face of the brand, Bondaroff’s Lower East Side omnipresence earned him the title "Downtown Don." After parting ways with Supreme, Bondaroff leveraged his experiences and relationships to create his own label, aNYthing. Short for “A New York Thing,” the name is notoriously the result of a trade, as Bondaroff—who initially thought of the name Undefeated—swapped brand titles with friend Eddie Cruz who coined “aNYthing.”

Central to aNYthing was its logo, a New York Giants flip that was a direct nod to the New York-centric nature of the brand. What made aNYthing was the brand rollout. The first batch of aNYthing logo tees were friends and family exclusives, which considering Bondaroff’s extensive network helped build a significant buzz preceding any sort of formal launch. When Bondaroff felt ready to publicly release items from the line, he prepared a lookbook that featured a cast of Lower East Side OGs including photographer Ricky Powell and the late-skater Harold Hunter. Bondaroff realized they key to building genuine hype was limited supply and authenticity, a formula that has since been adopted across the industry.

While Bondaroff's reputation is now sullied due to a string of sexual misconduct allegations, the aNYthing logo tee is still an important piece of New York streetwear's legacy, setting the standard in the art of cultivating organic buzz.

When brand founder Shawn Stussy debuted the first Stussy World Tour T-shirt in the fall of 1989, he had no idea how influential the shirt would become. Juxtaposing two radically different cultures, the front of the tee included fashion capitals—New York, London, Paris—in formal Helvetica type, while the names of boroughs where street culture was actually thriving were on the back.

In 2006, Stussy celebrated the shirt's 25th anniversary with the World Tour Project. The brand selected over 40 artists to do their own renditions of the World Tour design. The collaborators came from across different disciplines that included graphic designers, graffiti artists and streetwear legends. The T-shirts were released in small groups starting in March with additional designs dropping throughout the year. The standout was a collaboration with graffiti legend Futura (who, as we noted above was already a pervasive force in streetwear).

Considering Futura’s legacy his design was one of the most sought-after from the entire project. Showing off Futura’s signature hand-drawn style, the shirt shouts out cities that are meaningful to the artist—including Brooklyn, Atlanta and Venice. While both Futura and Stussy were notable streetwear names in their own right, their collaborative design was a bicoastal effort which showcased that streetwear had not only swept up both costs, but was now global.

In 2005, BAPE officially expanded to North America with the opening of its New York flagship store in SoHo. Although rappers such as Biggie and Lil Wayne had worn BAPE for years, the brand was receiving more attention stateside largely due to NIGO’s association with Pharrell. While the camo hoodies did numbers, BAPE’s footwear was particularly successful in the states. This includes the Bapesta, which became a status symbol amongst sneakerheads.

Arguably the first up-market knock off, the clear homage to the Air Force 1 was widely coveted for its bright colorways, limited nature and high price point.

The design was greeted with a combination of skepticism and disdain from many Nike purists. While some sneakerheads hated the design and claimed it was a blatant rip-off, others readily adopted the style. The most popular Bapestas were those decked out in candy colored patent leather as there was simply nothing similar on the market at the time. A series of collaborations with everyone from Marvel Studios to Kaws—and even Kanye West—helped raise the profile of the sneaker even further.

Like the Supreme x Nike SB Dunk Low, the Bapesta helped introduce sneakerheads to an entirely new category of clothing. As BAPE continued to expand, 1ST Camo hoodies became the de-facto sneakerhead uniform, proof that customers were willing to shell out for more than just limited kicks. The Bapesta—and BAPE by proxy—proved that streetwear brands could charge a luxury price point as long as the product quality and exclusivity justified it.

While streetwear collaborations were commonplace in 2006, this tee from Union upped the ante in every conceivable way. The “Return of the Mecca” T-shirt celebrated the reopening of Union Los Angeles in 2006 following Chris Gibbs' purchase of the store from former owner (and Undefeated boss) Eddie Cruz. An ode to the streetwear community, the shirt was a shout out to the brands affiliated with Union that had helped propel the shop to success and marked a new chapter as Union paved the way for a new sort of luxury streetwear boutique.

While the front of the T-shirt features a simple screen print stating “Return of the Mecca,” the back is absolutely flooded with logos from Supreme, WTAPS, Neighborhood, J Money, aNYthing and Stussy—all stocked at Union’s NY or LA locations at one point or another. The shirt portrayed the idea that these labels were more than just individual brands, but formed a community of like-minded creatives from around the world. In the 12 years since, Union has transitioned a number of times, with owner Gibbs curating the store to present the most current version of elevated streetwear. If anyone predicted the rise of luxury streetwear, it was Gibbs. This shirt marks the moment that started it all.