While The Notorious B.I.G. may not have been a BIG sneakerhead, he definitely rocked some of the most popular kicks of the ’90s. The rapper was seemingly drawn to chunkier silhouettes, such as the Reebok Questions and Nike Air Griffey Max 1s, and we all know his affinity for a pair of Timberland boots. But the “sky was really the limit” for what he would wear. Let’s take a look back at some of Biggie Smalls’ best sneakers throughout his career.
Air Jordan 12
Biggie wasn’t a huge sneakerhead, so Jordans weren’t really his go-to shoes. But he did wear a pair of Cherry Red Jordan 12s the year they were released. The sneakers came out in January 1997 (the year the rap legend passed away). Who knows, maybe the Notorious BIG could have become a bigger Jordan Brand fanatic after wearing these white and red beauties.
Clark Wallabee
Clarks’ Wallabees were popular on the b-boy and hip-hop scene in the ’90s. So, of course, one of the most stylish rappers of the time would have a pair or two. Biggie most notably threw on a beige pair of Wallabies to the Billboard Music Awards in 1995, the year he won Rap Single of the Year.
Nike Air Griffey Max 1
The bold, chunky, strapped-up Air Griffey’s originally dropped back in 1996. Who was spotted wearing them that same year? Biggie Smalls, of course. The rapper sported a black and white pair for a performance at Stony Brook University. Luckily, this silhouette is expected to make a comeback in 2026, hopefully in this Biggie-approved black and white colourway as well.
Nike Air Max 95
Big Poppa was even captured wearing what appears to be an all-white Air Max 95. Designed by Sergio Lozano, the silhouette debuted in 1995 in a variety of colours, but funnily enough, none of them were white. Could this be an unreleased sample? Maybe.
Nike Air Max Tailwind ’96
The Notorious B.I.G wore an unsung hero of ’90s sneaker culture during his performance at the HoodStock Festival in Harlem back in 1996. The Nike Air Max Tailwind ’96 was regarded as one of Nike’s top runners of the decade and integrated the brand’s Tailwind silhouette into the larger Air Max family. They were chunky, made of plush leather and terry cloth for the upper.
Nike Air Mission
Another chunky, strapped mid ’90s silhouette Biggie Smalls wore was the Nike Air Mission. The rapper wore these kicks to a photoshoot at Conart studios in 1994. Will Smith wore a similar mostly black pair for the first “Bad Boys” film in 1995, so it’s safe to say that this style was popular at the time.
Nike Air Trainer SC
Baseball and football player Bo Jackson’s Air Trainer SC High also made it onto Biggie’s feet in the 90s. The rapper was photographed in a black and grey “Raiders” colourway in 1994, the year his first album, “Ready to Die”, came out.
Reebok Question
Biggie, Biggie, Biggie “hypnotised” his fans with the Reebok Question sneakers he wore in his 1997 music video. The Reebok Question was a popular basketball sneaker at the time, known as one of Allen “The Answer” Iverson’s signature models. Its chunky design matches the sneaker style that the rap legend seems to have reached for more often. You can spot it at the 2:05 time stamp of his “Hypnotize” music video.
Timberland Boots
If there’s any shoe style that most of us associate with The B.I.G, it’s a pair of tan Timberland boots. He wore it in a number of videos, appearances, and photoshoots before his passing. So much so that Timberland even chose to honour the late rapper with a Christopher Wallace Collection for the 30th anniversary of his debut album, “Ready to Die.”
Bonus Notorious BIG Sneakers
Big may not have had any sneaker collabs while he was still alive, but plenty of brands have honoured him with special edition releases since. From Jordan Brand’s black and red AJ 13s to Fila’s two takes on the Tennis 88 silhouette and even a PUMA and Coogi teamup on two limited-edition Clyde sneakers. What makes these collabs so perfect is that they each nail a unique aspect of Biggie’s iconic style and influence on the fashion world.
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