Year Released: 1990

Michael Jordan wore this iconic OG colorway on the road throughout the 1990 NBA Playoffs, which included a grueling seven-game Eastern Conference Finals with the rival Detroit Pistons. This original colorway featured a predominantly black upper with metallic grey accents, which ranged from a speckled metallic midsole, to the Nike Air logo on the heel and the Jumpman logo on the accentuated tongue.

The original didn’t feature the now-signature “23” stitched along the side, however subsequent retro versions have since added it. The first retro version from 2000 is most true to the original form, while the 2016 retro reverted back to a lot of the original trappings, including the Nike Air logo, which made its triumphant return to the back heel for the first time in 16 years.

Year Released: 1990

The “Fire Red” colorway of the Air Jordan V may, at first glance, seem pretty similar but they are actually very different. Originally released in 1990, the “Fire Red” Jordan V feature subtle design tweaks that set it apart, despite being a predominantly red and white colorway—a common color pattern for Jordan Brand—and almost identical to the other kicks which Jordan himself rocked on the court during the 1990 season.

What sets the “Fire Red” pair apart from the rest of the OG models released in 1990 is that it was the first to feature the “23” stitching on the side heel. The “23” is now synonymous with Jordan Vs, and that 30-year lineage can be traced back to the original “Fire Red” pair. The “Fire Red” pair also boasts a black Nike Air logo on the heel and a matching black tongue, with a red midsole.

Year Released: 1990

Out of all the Jordan Vs ever produced, the “Grape” colorway has—in particular—managed to transcend the court and become a fixture in pop culture more than the rest, thanks in large part to its connection with a beloved ’90s sitcom and Hollywood icon. It became, unequivocally, one of the most popular non-Chicago Bulls-themed Air Jordan colorways of all time.

During Will Smith’s star-making turn on The Fresh Prince of Bel-Air, he always rocked an assortment of Jordans to match his fun, neon, early-’90s wardrobe and no sneakers stood out on the screen quite like his “Grape” Jordan Vs. Worn by Smith in everything from promotional shoots to his starring role on screen, the “Grape” Jordan Vs and Fresh Prince will forever be linked. This connection is so strong, Jordan Brand released a “Fresh Prince” Jordan V in 2018, paying homage to the longstanding bond between the two entities.

Year Released: 2000

One of the most famous stories in the Jordan mythology is when he was unceremoniously cut from his high school varsity basketball team as a sophomore. The incident served as a notorious motivator for Jordan throughout his playing career. So much so, that he mentioned it in his infamous Hall of Fame induction speech in 2009.

This “Laney” Jordan V Retro from 2000 pays homage to those formative days at Laney High School in Wilmington, North Carolina. Laney’s Royal Blue and Yellow color palette accentuated the white leather upper, while the blue and yellow “23” is stitched along the side—which, before his NBA days—also happened to be Jordan’s high school number.

Year Released: 2009

Back in 2009, Jordan Brand was in the midst of releasing all of its signature models as a part of “Countdown Packs” and other select pairings. The Jordan V received its own unique pack, dubbed the “Raging Bull.”

The pack featured two Vs, one in a full black nubuck upper with reflective accents and the other in beautiful red suede, the latter of which is featured here. Designed to pay homage to the red bandanas worn at the infamous Running of the Bulls in Pamplona, Spain, this all-red pair is a really cool and unique iteration of the Jordan V and one of the most popular new products from that slew of packs released in 2009.

Year Released: 2011

Jordan Brand’s “Bin23” program set out to craft more upscale, luxurious takes on its premium sneaker silhouettes, all of which tended to carry more of a hefty price tag. While some of the “Bin23” selections featured nods to Jordan’s love of cigars and the finer things in life, these Jordan Vs didn’t get too cute, simply taking the classic “Black/Metallic” colorway and turning it up a few notches.

The entire upper is constructed of premium black leather, as well as a tonal mesh sidewall. All of the other design features are old standby Jordan V traits–like the toggle lacing system and a speckled metallic midsole, just to name a few. The signature “23” stitching along the side is a matching black leather and there’s the “Bin23” red wax seal logo on the back heel, a signature mark of this elevated collection.

Year Released:2011

With all the history and pop culture cache associated with the Jordan V, it’s somewhat ironic that this quietly released, hyper-limited V celebrating the opening of the Jordan 23 store in Japan, is arguably the rarest and most expensive Jordan V ever produced.

This sneaker was released in limited numbers exclusively in Japan back in 2011. It’s also a departure from a lot of the Bulls-centric colorways that populate this list. The upper is clad in yellow suede, featuring wolf grey and black accents, with a matching speckled midsole. The most noticeable design tweak is the Chinese characters on the heel representing the number 23, a new take on the classic “23” stitching we’re accustomed to seeing.

Year Released: 2011

Jordan Brand helps run the “Quai 54” streetball tournament in Paris every year. In addition to featuring some of the greatest streetball players from all around the globe, Jordan Brand outfits the tournament with apparel and releases a signature sneaker for each year.

In 2011, the V was selected to represent that year’s tournament. It’s become one of the most popular “Quai 54” models ever released, most of which focus on bright neon accent colors, like the Radiant Green featured on this V. Black and Radiant Green highlight the white leather upper and it’s topped off with the Quai 54 logo on the heel. A “Friends and Family” pair was released alongside this version, in very limited quantities, with a black upper.

Year Released: 2015

It was a long time in the coming when Jordan Brand and Supreme linked up in 2015 for a small capsule collection of apparel and a collaborative take on the Air Jordan V. Originally released in three colorways–white, black and desert camo–this stands as Supreme’s first-ever Jordan Brand collaboration.

The sneaker features Supreme and Jordan co-branding throughout, from the clear sole to the inside tongue tag. “Sup” branding can be found printed inside the mesh netting along the sidewall, with the number “94” stitched along the heel (the year Supreme was founded), marking a rare moment a number other than “23” was found on the Jordan V.

Year Released: 2019

Leave it to Michael Jordan’s son Marcus to take one of his most celebrated sneakers and design one of its best iterations in years. This Ice Blue Jordan V was released under Marcus’s “Trophy Room” imprint–his Florida-based sneaker store which pays homage to Michael Jordan’s actual Trophy Room from the old family home in which Marcus grew up–in 2019 to much fanfare and hype.

Releasing 7,000 pairs, the “Trophy Room” Jordan V was one of the best sneaker releases of 2019. The upper is constructed of an Ice Blue suede with red and white accents throughout. What makes these really cool is the numbers stitched on the sides. On one sneaker is the traditional “23” and the other is a “5” which is the number Marcus wore while at UCF. On the back heel is a Jumpman logo on one shoe and the Trophy Room logo on the other. A red suede “Friends and Family” pair (pictured here) released in conjunction with the main Ice Blue version and was limited to just 223 pairs.