Austrian-born Helmut Lang is a New York-based artist and former menswear designer who was renowned for his preternatural ability to create collections that brought together disparate influences to create a minimal and uniquely wearable aesthetic that has been echoed by fellow designers and brands ever since. With inspirations ranging from rom bondage straps to repurposed military clothing, flight suits and painter pants, his collections often featured several innovative and highly covetable pieces. His late '90s collections in particular have become the most collectible. The pillow neck jacket debuted in his Autumn/Winter 1999 collection, incorporating a bondage influenced internal carry harness and cargo pockets with a buttoned detachable packable rain hood, which doubles as a neck rest clearly inspired by the kind often worn by travelers on long flights. This iteration, done in a lightweight dark navy cotton/poly blend, is a perfect outer layer that can easily be stowed away or carried in warmer weather or worn as a shell in more temperate climates.

Raf Simons' Autumn/Winter 2001 "RiotRiotRiot" and Spring/Summer 2002 "Fear Generation" collections are known for the iconic patchwork designs that have made Simons synonymous with the trends that other designers are just getting into today. However, the mid 2000s gave way for his diffusion line, Raf by Raf Simons, to repurpose and reimagined the designs that had brought him to such critical acclaim, but with a different story. Most notably, "New Tribes" featured patchwork pieces that alluded to a new society created out of rebellion. Buildings, cities, flags and various other community signifiers were pictured alongside the slogan "Raf Simons for New Tribes." This sleeveless crewneck sweatshirt comes complete with similar distressed patchwork details found in both the aforementioned "RiotRiotRiot" and "Fear Generation" collections, but with statues that would be embraced in Simons vision of urban planning.

Photographer and filmmaker Ari Marcopolous moved to New York City in the early '80s where he got his start assisting the likes of Andy Warhol and Irving Penn. By the early '90s, he had established a cult following and already had an extensive history of creating intimate portraits of the city's subculture icons, from Public Enemy and Run DMC to Keith Haring and Dennis Hopper, when a chance encounter with professional skateboarder Jeff Pang at the Brooklyn Banks led him to take the now iconic portraits of the late Harold Hunter and Justin Pierce at the same time Larry Clark was beginning to film Kids. Supreme opened their doors on Lafayette in 1994 and would later fill the space with a collage of Marcopolous' photos of local skateboarders. In 1996, they released this T-shirt with Marcopolous' early portraits of the late Jean-Michel Basquiat as a tribute to both Supreme and Marcopolous' roots. Supreme has gone on to do several collaborations with Marcopolous over the years, making his photographs an integral part of the brand's DNA and history, though this T-shirt from their first collaboration is inarguably one of the rarest and most covetable.