The Jordan franchise changed the world of sneakers forever. Without the storytelling and collectible influence that Jumpman sneaks introduced, would sneakers hold anywhere near as much value as they do today? Probably not. The Jordan saga stretches over a 36-year period, featuring grailed releases, hyped rereleases, and releases we’ll probably never see again. That’s a storyline worth following.

Our favorite part of that storyline took place in the decade beginning 1995. Many see this era as the golden years of Jordan brand, birthing many of the silhouettes that populate top-10 and most-wanted lists today. In honor of these hallowed years, we’ve linked up with eBay to round up 10 of the best Jordans that released between 1995 and 2005.

What’s perhaps most interesting about our list is the clear difference in the popular silhouettes. While the Jordan 1 is the dominant silhouette right now, the Jordan 3 and 11 held huge power during the 1995-2005 period. As style swings its unstoppable pendulum, we’ve no doubt that these silhouettes will experience a heyday again, so it might be worth investing now. The best part is that eBay Canada now offers an Authenticity Guarantee on Jordan sneakers $100+ so you can invest with confidence.

Shop the best Jordans that released between 1995 and 2005 at eBay below.

The prices listed are our lowest buy-now finds at the time of publishing. They are not exact and may differ.

1995 Air Jordan 11 OG Concord

Air Jordan 11 OG Concord

Air Jordan 11 OG Concord

$2010

Nike

Buy at ebay

Released in November 1995, the Concord was the first colorway of the Jordan 11. Inspired by convertible cars, the silhouette features a black patent leather mudguard against a white Cordura ballistic nylon upper like the body of a car with no roof.

1997 Air Jordan 12 Flu Game

Air Jordan 12 Flu Game

Air Jordan 12 Flu Game

$409

Nike

Buy at ebay

We spoke about the power of storytelling in the Jordan franchise and few Jordans come as steeped in history as the 1997 Jordan 12 Flu Game. Worn by Michael Jordan as he battled flu-like symptoms (said to have been brought on by a poisoned pizza) to guide the Bulls to a Game 5 victory in the 1997 NBA Finals, this pair holds serious nostalgic power.

1999 Air Jordan 14 Last Shot

Air Jordan 14 Last Shot

Air Jordan 14 Last Shot

$271

Nike

Buy at ebay

Talk about nostalgia. Any Chicago Bulls fan — scratch that. Any basketball fan should feel a pang of sadness and respect when they see the 1999 Air Jordan 14 Last Shot. This was the last pair that Jordan wore as a Bull while he sank the game-winning shot against the Utah Jazz to win his sixth trophy.

2000 Air Jordan 11 Space Jam

Air Jordan 11 Space Jam

Air Jordan 11 Space Jam

$327

Nike

Buy at ebay

On the heels of the release of the universally ridiculed Space Jam reissue, we had to include the 2000 Air Jordan 11 Retro Space Jam. The original released in 1996 was the pair that Mike wore to play the Monstars in Space Jam, but this 2000 Retro is definitely easier to get your hands on.

2001 Air Jordan 11 Cool Grey

Air Jordan 11 Cool Grey

Air Jordan 11 Cool Grey

$201

Nike

Buy at ebay

Remember when Jordan played for the Wizards? 2001 was a weird year. The whole situation was somewhat rescued by the fact that he wore the Air Jordan 11 Retro Cool Grey on occasion. As well as being a high-performance shoe for hooping, the nubuck grey uppers of this pair make it a perfect lifestyle crossover.

2001 Air Jordan 3 Mocha

Air Jordan 3 Mocha

Air Jordan 3 Mocha

$211

Nike

Buy at ebay

In 2021, Mocha is a keyword in sneakers. With an uptick in the interest in neutral colorways — and a certain Travis Scott design — brown sneakers are in high demand. The Air Jordan 3 Mocha was released a solid 20 years ago and you can pretty much guarantee nobody else will be rocking these at the function.

2003 Air Jordan 3 White Cement

Air Jordan 3 White Cement

Air Jordan 3 White Cement

$646

Nike

Buy at ebay

As far as Air Jordan 3s go, the Air Jordan 3 White Cement is as clean and as classic as they come. One of the original colorways from the silhouette’s first release in 1988, it got Retro treatment in 1994, 2003, and 2011. We think the 2003 reissue is the golden mean.

2003 Air Jordan 1 Patent Black/Gold

Air Jordan 1 Patent Black/Gold

Air Jordan 1 Patent Black/Gold

$159

Nike

Buy at ebay

The only Jordan 1 in today’s roundup, the Patent Black/Gold iteration which dropped on December 23, 2003 is flying the flag for the style. This reup of the wildly rare 1995 drop features a full patent leather upper for a bold finish in tandem with the gold Swoosh and Jordan detailing.

2004 Air Jordan 7 Olympics

Air Jordan 7 Olympics

Air Jordan 7 Olympics

$301

Nike

Buy at ebay

We’re sad to see Tokyo 2020 finish, but this pair of 2004 Air Jordan 7 Olympics proves that the Olympics can live on for much longer than their allotted fortnight. Designed to commemorate the jerseys worn by the US team for Barcelona ’92, this pair features an unusual ‘9’ to the heel where the signature ’23’ usually sits.

2005 Air Jordan 20

Air Jordan 20

Air Jordan 20

$201

Nike

Buy at ebay

Released for Jordan Brand’s 20th anniversary, the Air Jordan 20 is not a smash-hit silhouette. In fact, we’d bet that a good portion of Jordan fans hasn’t ever seen a pair. Designed by the legendary Tinker Hatfield, it’s an underrated, unorthodox silhouette for those looking to grab something that never quite took off.

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