In sneaker culture, not every drop is created equal. Some pairs hit hard for a week and then fade into resale background noise. But every once in a while, a release doesn’t just sell out, it takes over. The internet crashes, resale charts spike, and a new grail is born.

 

These are the pairs that changed everything. The ones that defined eras, built resale markets, and still move conversations years later. I’ve ranked five of the biggest grails that broke the internet based on impact, staying power, and tradability today, and I’ll also break down which ones are the smartest investments right now.

 

1. Off-White x Air Jordan 1 “Chicago” (2017)

When Virgil Abloh dropped The Ten, it reset the whole sneaker landscape. But the Off-White Air Jordan 1 “Chicago” wasn’t just the standout of the pack; it became one of the most important sneakers of the last decade.

 

Virgil deconstructed a classic, leaving exposed foam, visible stitching, and his now-iconic zip tie. According to anyone who lived through that drop, it wasn’t just a shoe, it was a cultural turning point.

 

Retail Price: $190

Peak Resale: $8k-$10k+

Current Value (2025): $4k-$9k

 

Hype Health: Still sky high. The Chicago colorway ties it to Jordan history, while Virgil’s passing elevated its status even further. This shoe isn’t going anywhere; it’s already cemented as a legend.

 

Tradability: High. Unlike ultra-rare unicorns, this one actually trades often. There’s always demand if you’ve got a clean pair.

 

2. Nike Air Yeezy 2 “Red October” (2014)

This was the moment Nike and Kanye West ended with a bang. No warning, no buildup, Nike shock-dropped the Red October on a Sunday morning and the internet went into chaos. All-red, futuristic design, gold lace tips, and Kanye in his prime. It was more than a sneaker; it was a mic drop.

 

Retail Price: $245

Peak Resale: $15k-$25k+

Current Value (2025): $10k-$20k+

 

Hype Health: Untouchable. The Red October is beyond sneaker culture now, it’s mythology. Even with Kanye’s complicated legacy, this shoe’s place in history is locked.

 

Tradability: Medium. There are buyers lining up, but pairs are insanely scarce. These don’t move fast on resale apps; they’re more likely to change hands in auctions or through high-end consignments.

 

3. Travis Scott x Air Jordan 1 High “Mocha” (2019)

The backward Swoosh. The brown suede. The Travis co-sign. This release turned Travis Scott into a true sneaker icon. Some even called them the new Chicago 1s, not quite, but the impact is undeniable.

 

Retail Price: $175

Peak Resale: $2k-$2.5k

Current Value (2025): $1.2k-$2k

 

Hype Health: Still going strong. Travis has stacked collabs since, but this pair remains the crown jewel. It’s hype, wearable, and tied to one of the biggest artists in the culture.

 

Tradability: Very High. These move constantly. If you want a grail that doubles as trade bait, the Travis AJ1 High Mocha is unmatched.

 

4. Dior x Air Jordan 1 (2020)

When Dior linked with Jordan Brand, it blurred the line between streetwear and luxury in a way that actually worked. Premium Italian leather, Dior monogram Swoosh, and a super-limited run. This wasn’t just hype; it was a statement that sneakers had fully crossed into high fashion.

 

Retail Price: High $2,000 | Low $2,200

Peak Resale: $10k-$15k

Current Value (2025): High $7k-$12k | Low $5k-$9k

 

Hype Health: Still premium. While prices cooled slightly after the frenzy, the Dior 1 remains a staple grail. It’s one of the few pairs that feels just as at home in a sneaker vault as it does in a luxury collection.

 

Tradability: Medium. The high-ticket price narrows the buyer pool, but complete sets with all accessories still command serious attention.

 

5. Supreme x Nike SB Dunk Low (2002)

Supreme has been driving hype since day one, but the 2002 SB Dunk Lows might be their crown jewel. Croc leather, gold stars, and insane scarcity turned them into instant grails.

 

In 2021, Supreme revisited the formula with another round of SB Dunk Lows, and history repeated itself, the internet went crazy, proving that Supreme can still flip the culture on demand.

 

Retail Price: OG $65 - $70 

Peak Resale: OG $20k+ 

Current Value (2025): OG $15k - $25k+

 

Hype Health: The OGs are historic artifacts, more like museum pieces than sneakers. The 2021 versions are more accessible but still hold steady resale.

 

Tradability: OG = Low-Medium. Only the top collectors chase them. 2021 = High. Easy to move and perfect for everyday collectors.

 

Final Ranking

Here’s how I rank these five grails today:

 

1.     Off-White Air Jordan 1 “Chicago” - Era-defining, still tradable, and tied to Virgil’s legacy.

2.     Nike Air Yeezy 2 “Red October” - Myth status, impossible to replace, but less liquid.

3.     Travis Scott Air Jordan 1 High “Mocha” - Most liquid grail of the modern era.

4.     Dior Air Jordan 1 - Luxury crossover with lasting prestige.

5.     Supreme SB Dunk Low - History-defining OGs, with 2021 pairs keeping the energy alive.

 

Investment Ranking: Which Grails Are Smartest to Play?

Not all grails are equal when it comes to investment. Some are long-term holds, others are quick movers, and a few are best treated as collector pieces that gain value slowly. Here’s how I’d rank them for ROI potential:

 

1. Travis Scott AJ1 High “Mocha” - Best Short-Term/Trade Play

Why: Most liquid grail out there. You can flip these quickly, use them as trade bait, or sit on them short-term with confidence.

Play: Ideal for resellers or collectors looking to level up into higher grails.

 

2. Off-White AJ1 “Chicago” - Best Long-Term Hold

Why: It’s Virgil’s legacy piece and one of the most important sneakers of the modern era. Prices may seem steep now, but in five or ten years, they’ll look cheap.

Play: Treat it like an art piece. The longer you hold, the more it cements itself as untouchable.

 

3. Dior AJ1 - Premium Collector Investment

Why: High entry point, smaller buyer pool, but unmatched in the luxury crossover lane. Dior proved sneakers belong on the runway, and this pair will always be remembered as the one that did it.

Play: Hold with full set (dust bags, booklet, tags). Moves slower, but worth it for the right buyer.

 

My Take

Grails aren’t just about resale prices; they’re about the way they shape culture. The Off-White Chicago AJ1 is number one because it’s still tradable while holding its place in history. The Red October is pure legend, untouchable in myth. Travis’s Mocha 1s are the most practical grail for anyone looking to flip or trade. The Dior 1 brought sneakers into true luxury territory. And the Supreme SB Dunk proved hype can come full circle across decades.

 

If you’re collecting for passion, hold what speaks to you. If you’re investing, know the lanes: Travis for liquidity, Off-White for long-term growth, Dior for luxury positioning. Either way, these grails remind us why we’re in the game. They aren’t just sneakers, they’re stories you can wear, trade, and remember forever.