Year: 2020
Listing Price: $1,250
Size: 10.5

Released back in February, Virgil Abloh’s deconstructed take on the Jordan V picked up where he left off on the Jordan I. Sporting a faded black/grey “Muslin” colorway, this Jordan V sports the same reflective metallic silver tongue from the “Black/Metallic” OGs, albeit with a new noticeable hole. The soles come pre-yellowed for an authentic vintage feel, Nike Air branding can be found on the heel, and all of Abloh’s signature text and quotations can be found throughout, particularly on the laces and on the side panel mesh.

Year: 2012
Listing Price: $320
Size: 8.5

When Jordan Brand released a retro version of the Jordan IX “Olive” in 2012, sneakerheads were geeked. As an OG colorway, the “Olive” IXs really stand on its own due to its unique presentation. Decked in a black and olive colorway, the shoe takes on an almost boot-like look, featuring the faintest hints of red sprinkled throughout. Looking back, it stands out among the traditional Bulls-inspired colorways, however when this sneaker was originally released in 1994, Jordan was retired and playing baseball, so it made perfect sense for the brand to try something different, something a little more “off-court.”

Year: 2019
Listing Price: $5,400
Size: 15

It’s nice to see that Georgetown doesn’t hold a grudge against MJ for hitting the game-winning shot during the 1982 NCAA Championship Game. Georgetown is one of the few schools, along with Jordan’s alma mater UNC, Michigan and others, who are outfitted by Jordan Brand. This means, of course, that they are often the recipient of exclusive Jordan PEs, like the Georgetown-flavored Jordan IV in this listing. Issued to members of the team and staff, this Jordan IV features a Cool Grey upper with a speckled grey midsole. An icy sole pops at the bottom, while a speckled Navy heel tab adorns the Jumpman logo. It’s finished off with a Georgetown tag stitched onto the tongue.

Year: 2012
Listing Price: $200
Size: 9.5

Worn by the talented and versatile two-sport stud Deion Sanders, this was the second iteration of the Diamond Turf line. The OG colorway, which pays homage to Sanders’s Super-Bowl winning time with the San Francisco 49ers, was originally released in 1994, followed by a proper retro version in 2012. Matching some of the best uniforms in football, this pair of Diamond Turf IIs features a red upper with metallic gold mesh panels for a lighter, breathable feel. It also comes with a midfoot strap for an added touch, along with a black and white Air-cushioned midsole. Like Deion said, “If you look good, you play good,” and he always “played good” in the Diamond Turfs.

Year: 2015
Listing Price: $250
Size: 6

The great Andre Agassi was one of the most popular athletes on Nike’s roster throughout the 1990s. Aside from his on-court skill, his on-court style was something to behold. With the help of Nike, Agassi wore all types of bright colors and broke out different looks in both his apparel and footwear, a far cry from the traditional all-white looks in professional tennis. The Air Tech Challenge III was originally released in 1990 and worn by Agassi. The 2015 retro is the version found in this listing and stays true to Agassi’s flashy on court aesthetic. This “Volt” colorway features a perforated leather upper with a neon cage. There’s a rather large graphic of a tennis ball on the heel, as well as a visible Air unit.

Year: 2013
Listing Price: $170
Size: 9

Originally released in 1997 as the signature sneaker for Allen Iverson, the Answer DMX 10 is a stark change in color scheme from Iverson’s Reebok Question, as the 76ers were in the midst of rebranding from their traditional red, white and blue aesthetic to a more modern black and gold feel. Reebok would retro the sleek shoe in 2013 for an Anniversary release, which is the version featured in this listing. Sporting a black and white upper with gold accents, the Answer DMX 10 featured a concealed lace system and debuted Iverson’s classic “I3” logos. Another notable feature was that it was the first Reebok shoe to debut “moving air technology,” which transfers air throughout the shoe in response to your stride.

Year: 2009
Listing Price: $201
Size: 9

Originally released in 1996, the Penny II was the next step in the evolution of Penny Hardaway. His teammate Shaquille O’Neal left Orlando in the summer of 1996 during free agency, and the Magic was effectively Penny’s team. The Penny II accompanied him throughout that year of growth, which eventually led to a playoff berth. Originally releasing in three Orlando-centric colorways, the “Atlantics” received a retro release in 2009, hitting all the highs of the original. Sporting a white leather upper with Atlantic Blue durabuck underlays, the Penny II featured Hardaway’s “1Cent” logo on the tongue and featured a Phylon support wing, which was reinforced with a carbon fiber plate. The midsole features a Zoom air unit as well as Max Air cushioning in the heel for a cozy on-court fit.

Year: 1997
Listing Price: $135
Size: 8.5

The following year, Nike got even more creative with the Penny line with the release of the Penny III. Staying true to the Orlando color schemes, the Penny III introduced the revolutionary Foamposite technology on the shoe’s side panels with a wavy matte blue look. Once again featuring a Max Air bubble by the heel, this was the last real high of the Penny line, which was really one of the more popular non-Jordan lines of the era. Nike is bringing this silhouette back once again, with a retro release of the “Eggplant” Penny III hitting stores this month.

Year: 2019
Listing Price: $195
Size: 8

Known as both the Fila ‘96 and the Grant Hill 2, this silhouette from Fila was (you guessed it) the second signature sneaker for NBA superstar Grant Hill and was originally released in 1996. Definitely the biggest NBA star on the Fila roster in the 1990s, Grant Hill made Fila kicks cool on the court. The Fila ‘96 features a white leather upper with navy patent leather trim throughout. The design has seen many retro releases over the last 24 years, but the pair featured in this listing is from the most recent retro release in 2019.

Year: 2007
Listing Price: $178
Size: 11

Originally released in 2007, this pair of low-top Air Force 1s pays homage to the “Round Mound of Rebound” Charles Barkley and his time with the Phoenix Suns. After being traded to the Suns in 1992, Barkley immediately changed the team’s fortunes. He would win MVP during the 1992-93 season and dragged the Suns to the precipice of a title before losing to MJ’s Bulls in six games during the 1993 NBA Finals. These Air Force 1s, dubbed the “Barkley Pack,” sport a black upper with purple leather accents on the Swoosh and upper paneling, with orange cross-stitching throughout the tongue and midsole, producing a look similar to the Suns’ jerseys, especially their black alternates.