The Top Pick and How These Three Air Jordan Retro Releases Fit Together
This guide to upcoming Air Jordan retro releases explains the key dates, colorways, and design details for three major drops so collectors can prioritize which pairs to buy over the next 18 months.
If you only lock in one pair, make it the Air Jordan 12 Obsidian. It is the only original Air Jordan 12 colorway that Michael Jordan never wore in an NBA game, yet it became a collector favorite thanks to its clean navy leather, white overlays, and Carolina blue accents. With a high-top build and a release set to align with the colorway’s 30th anniversary, it is the most historically anchored and wearable option in this sneaker release schedule. The three drops land on August 14, 2026 (Air Jordan 9 Low Kilroy), January 23, 2027 (Air Jordan 12 Obsidian), and May 22, 2027 (Air Jordan 9 Gym Red), giving you a clear calendar of opportunities across 18 months.
Air Jordan 9 Low ‘What The Kilroy’: Mismatched Storytelling on Foot
The Air Jordan 9 Low ‘What The Kilroy’ is the most playful pair in this trio and the one to chase if you want loud, story-rich sneakers. Releasing on August 14, 2026, this low-top folds the entire 2012 Kilroy Pack into one mismatched design, pulling pieces from Johnny Kilroy, Motorboat Jones, Bentley Ellis, Slim Jenkins, Calvin Bailey, and Fontay Montana. The left shoe uses a mostly black build with dark blue on the lower half, orange on the midsole, yellow lining, and white laces, while the right shoe flips to red leather, black overlays, light blue lining, and black laces.
Tongue tags spell out each alter ego’s name, three stacked Jumpman logos sit on the insoles, and heel embroidery switches between ‘23’ and ‘4’, with ‘KILROY WAS HERE’ hidden behind the tongues. This is the pair for collectors who love deep-cut Jordan lore and visual chaos; it is the least subtle shoe in this release calendar and proudly so.
Air Jordan 12 ‘Obsidian’: The Everyday Anchor of Your Rotation
The Air Jordan 12 Obsidian is the release that anchors this entire run and the one that will work hardest in regular wear. First introduced in 1997 and retroed widely only once in 2012, it returns again on January 23, 2027 with a build that is expected to stay close to the original. The shoe uses a dark navy leather upper, a crisp white mudguard, and Carolina blue hits that tie back to Michael Jordan’s college days, laid over the stitched lines inspired by Japan’s Rising Sun flag.
Unlike most early Air Jordans, this colorway steps away from traditional team colors yet remains easy to wear with nearly any outfit. The high-top cut, classic paneling, and balanced palette make it the best all-rounder among these Air Jordan retro releases. If you want one pair that feels both historical and practical, make this your non-negotiable cop in the sneaker release schedule.
Air Jordan 9 ‘Gym Red’: Patent Pop with an Updated Shape
The Air Jordan 9 Gym Red is your bold, patent-heavy option, ideal if you like clean color blocking with attention-grabbing shine. Returning on May 22, 2027, this non-original colorway brings back the glossy patent leather design that first debuted in 2019 and has since become one of the silhouette’s most recognizable modern releases. It pairs a White leather upper with glossy Gym Red patent leather around the mudguard and midsole, Gym Red hits on the heel, collar, tongue branding, and parts of the outsole, and Black accents on the inner lining, Jumpman branding, and pull tab.
Underfoot, you still get the familiar Air Jordan 9 outsole with multilingual details and encapsulated Air cushioning, while the updated mold aims to better reflect the original shape. According to one report, “the ‘Gym Red’ Air Jordan 9 proves that memorable colorways don’t have to be part of the original lineup to leave an impression.” If you missed this pair in 2019, this general release is your second chance to add an Air Jordan Gym Red standout to your rotation.
Buy if / Skip if
- Buy the Air Jordan 12 Obsidian if you want one timeless, high-top retro that can anchor daily outfits and still satisfy collectors.
- Skip the Air Jordan 12 Obsidian if you prefer louder, experimental colorways and rarely wear navy-and-white sneakers.
- Buy the Air Jordan 9 Low Kilroy if you like mismatched, story-driven designs and want a single pair that condenses the entire Kilroy Pack.
- Skip the Air Jordan 9 Low Kilroy if you need a subtle pair for everyday wear or dislike heavily mismatched shoes.
- Buy the Air Jordan 9 Gym Red if you are drawn to patent leather and want a bold two-tone Air Jordan 9 with an updated shape.
- Skip the Air Jordan 9 Gym Red if you prefer matte finishes or understated color blocking in your Air Jordan retro releases.
- Buy the Air Jordan 12 Obsidian if you are planning your sneaker release schedule around historically significant, anniversary-aligned retros.
- Skip the Air Jordan 9 Low Kilroy if you collect only original or on-court colorways and avoid theme-heavy collaborations.
