Mar 13, 2025

The origins of streetwear

The objects and artworks from The Culture that illustrate hip hop’s influence on the world of fashion.

Installation view, The Culture: Hip Hop and Contemporary Art in the 21st Century, December 6, 2024 to April 6, 2025. Art Gallery of Ontario. Artworks © the artists. Photo © AGO

To say hip hop has influenced fashion is an understatement. It is quite literally responsible for the inception of streetwear as a concept and has been consistently present as a stylistic and cultural influence on runways since the 1980s. Similar to hip hop’s central art forms – emceeing, DJing, breakdance and graffiti – its fashion trends usually present themselves with a regional flare, beginning as local styles but often ending up enshrined in fashion history. This is true of single articles of clothing like Nike’s Air Force 1 sneakers as well as start-up streetwear brands like FUBU, Karl Kani or Toronto’s own Too Black Guys.

On view now at the AGO, the exhibition The Culture: Hip Hop and Contemporary Art in the 21st Century features streetwear, wigs and jewellery, as well as fashion-themed artworks, highlighting the intersection of hip hop and fashion. While illustrating how these two worlds are inextricably linked, the exhibition reminds visitors that the ripple effects of hip hop fashion are far-reaching and have likely influenced their personal style choices.

Take a closer look at some of the key objects and artworks in The Culture that reflect hip hop’s massive impact on the realm of fashion.

Too Black Guys

A staple Toronto streetwear brand, Too Black Guys was established in 1990 and rose to notoriety when their thought-provoking shirts were circulated widely throughout the hip hop community in Canada and abroad. Founder Adrian Aitcheson derived the name Too Black Guys from the Malcom X speech “Message to the Grass Roots” and was inspired as an entrepreneur by the “do for self” mentality of 90s hip hop. The brand has been championed by the likes of Ice Cube, Busta Rhymes and Mary J. Blige, who wore a Too Black Guys baseball shirt in her “Real Love” music video.

Installation view, Too Black Guys. [Too Black Guys Jersey Black], 1992. © Too Black Guys. Photo © AGO.

Four garments by Too Black Guys are featured in The Culture. As visitors enter the Brand section of the exhibition, placed on two mannequins are a Too Black Guys baseball jersey, Coming to America T-shirt, hockey jersey and a nylon vest.

Dapper Dan

During the 1980s and early 90s, Daniel Day (Dapper Dan) was a household name in New York City’s hip hop community. The tailor and Harlem native was famous for outfitting hip hop stars, professional athletes and even notorious gangsters in his signature “knock offs” of luxury fashion brands. Day would rework branded materials from companies like Gucci, Louis Vuitton and Fendi into garments made in the style of hip hop streetwear. In 2018, after being publicly called out for appropriating Day’s designs, Gucci opened an invitation-only atelier with Dapper Dan and supplied all the fabrics for his work there.

Installation view, Daniel Day, Guccissima Leather Down Jacket, Spring / Summer, 2018. © Daniel Day. Photo © AGO

Two of Dapper Dan’s designs are on view as part of The Culture. In the exhibition’s Brand section, visitors can find a red Gucci leather jacket and blue Bees tracksuit, both made by the streetwear legend.

Baby Phat

Following her marriage to the founder of Def Jam Records and Phat Farm Clothing Russell Simmons, former fashion model Kimora Lee Simmons became the president and creative director of Baby Phat in 1999. The brand quickly rose to global prominence as one of the first major hip hop streetwear companies catering to women only, and specifically, women of colour. Baby Phat’s original offerings included low-rise jeans and rhinestone decorated tops, but they would later release signature winter jackets, valour tracksuits and a range of accessories.

Installation view, Baby Phat, White Track Suit, c. 2000. © Baby Phat. Photo © AGO.

A mannequin outfitted in a white cotton Baby Phat tracksuit adorned with rhinestones is on view as part of The Culture. An essential representation of early 2000s hip hop fashion, this look reflects the monochromatic or two tone zip up tracksuits offered by most streetwear brands during the era.

Nike’s Air Force 1 Sneakers

The Air Force 1 – arguably Nike’s most famous shoe design – was first popularized as a staple of Harlem, NY streetwear in the mid 1980s. By 2002 the shoe became globally ubiquitous due rapper Nelly’s number one single “Air Force Ones”. Much like the Adidas shell toe, Nike’s Air Force 1s are more synonymous with hip hop than they are with athletics and have remained as essential streetwear globally for almost 50 years.

In The Culture’s Ascension section, visitors will encounter St. Louis born artist Aaron Fowler’s massive sculptural work, The Live Culture / Nike Air Force 1 (2022). Made using recycled car parts and other media, this large sculptural depiction of a pair of air force ones was made in honour of Fowler’s late cousin, who died following a tragic accident.

100 Miles

Toronto native Garie Adamson founded the iconic streetwear brand 100 Miles in 1992, the same year he opened his first flagship store on Yonge Street. After being connected to some key figures in the American hip hop industry through a relationship with renowned duo Kid n Play, Adamson’s brand became globally famous when Tupac Shakur wore a 100 Miles hoodie in the classic film Above the Rim. In reference to the scene, Drake wore the same hoodie courtside during the Raptors 2019 playoff run.

100 Miles T-Shirt. Photo AGO.

Although 100 Miles is not included in The Culture exhibition, visitors to the AGO can find a range of 100 Miles pieces currently available for purchase at shopAGO.

The Culture: Hip Hop and Contemporary Art in the 21st Century is on Level 5 of the AGO. The exhibition is co-curated by Asma Naeem, the Baltimore Museum of Art (BMA)’s Dorothy Wagner Wallis Director; Gamynne Guillotte, the BMA’s Chief Education Officer; Hannah Klemm, Saint Louis Art Museum (SLAM)’s Associate Curator of Modern and Contemporary Art; and Andréa Purnell, SLAM’s Audience Development Manager. The AGO presentation is organized by Julie Crooks, Curator, Arts of Global Africa and the Diaspora, AGO.