EDITOR’S NOTE

Happy Fall! Missed you!

Last week, Gameday Grails hit 10K on Instagram—a milestone we never saw coming. If you aren't following us yet, what are you waiting for?

I'll shout from the rooftops: The culture around vintage sportswear is infinitely more fascinating than the clothes themselves. Today, we're diving into an old-school editorial that reveals the underground secret of how top vintage collectors score $300 snapbacks for as little as $15.

No gimmicks, no scams—just pure collecting strategy.

THIS WEEK’S GRAILS

Just in time for the playoff run: this is what Cubs fans wore before Bartman, before the curse broke, before any of it.

This 1988 Starter satin Cubs bomber is pure North Side energy—back when the Cubs were lovable losers. That Cubbie blue colorway hits different in person, and the satin? Still got that shine after almost 40 years!

THE DETAILS:

• Original 1980s Starter construction (the real deal, not vintage-inspired)

• Royal blue satin that catches light like game day at Wrigley

• Marked size Large (but Starter satin jackets run a size down—fits more like a Medium)

• Pre-owned in solid condition with normal vintage character

HOMEFIELD HEATER OF THE WEEK

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10K followers

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The good folks @homefieldapparel sent over their 2025 Can’t Miss Kickoff box celebrating my beloved Noles, so I had to put it to the test. The standout piece is this hoodie that feels exactly like a 1990s Champion Reverse Weave. Not hyperbole, I compared it side-by-side with a team-issued Bulls reverse weave in the video because the weight and construction are shockingly similar.

THey have 45 schools available, so get yours and use code GRAILS15 at checkout

INSIDE INSTAGRAM’S UNDERGROUND VINTAGE HAT MARKET

@gamedaygrails

$300 HATS FOR $20 No gatekeeping here! Instagram Live raffles let you scoop authentic hats for a fraction of retail while supporting real ... See more

Forget eBay bidding wars and overpriced boutiques. The real action is on Instagram Live, where vintage hat raffles feel like a cross between Sotheby’s, a secret casino, and DraftKings…except the prize is a vintage snapback that’ll still hold value twenty years from now.

What Are Instagram Live Raffles?

Exactly what it sounds like. a vintage hat raffle that is executed exclusively on Instagram Live. Over the last two months, I experimented: $100 budget, 9 raffles, and a mission to document the underground economy of vintage hat collecting. Here's what I learned.

Over the last two months, we’ve been conducting a fun experiment. We set a strict $100 budget and entered 9 raffles, with entry prices ranging from $8 to $15.

How The Game Works

Picture this: You're watching live with 15 other collectors. The seller runs a Hangman-style game using a random number generator. The seller uses the randomizer to pick numbers, using them to fill in letters to spell words like "VINTAGE". Your number gets called—that's a "hit." You need 7 hits total to win. You've got 5 hits, need 2 more, and you’re now tied with another person…next hit wins.

The tension is unreal. Your heart actually races. When that hit lands and you realize you just won a $300 hat for $20? Pure adrenaline.

The Playbook: How to Win

Step 1. Find the Right Sellers

Start with these trusted accounts (I've personally vetted each one). These aren't just sellers—they're curators and collectors:

• @castrovintage916

• @thriftingthevalley

• @vtgnnguyen

Pro Tip: Turn on notifications. Treat this like fantasy football scouting.

Step 2: How to Enter a Raffle

Sellers announce raffles on their feed/stories. Each raffle typically has 15 numbered spots. Comment or DM to claim your number. You then pay immediately (usually $8-$15) via Venmo/Cashapp/etc. Oh, and include your preferred hat in the payment note.

Step 3: Build Credibility

• Pay fast. Waiting to pay = unserious person. You’re not an unserious person, are you?

• Engage authentically with sellers. Let them know your preferred teams or styles.

• Support their non-raffle content. Show love, a fire emoji can go a long way.

Why This Beats Traditional Collecting

This isn't just shopping—it's strategy. And while it might feel like gambling, you're betting on physical assets that have historically appreciated, supporting individual collectors doing this for the love of the game.

Plus, I got a mortgage and kids, man. If I can build a grail collection for less than a value meal? That's a win in my book.

Ready to start hunting? Hit reply and let me know what you're looking for. I'll connect you with the right sellers.

Disclaimer: Always collect responsibly. This is a community, not a get-rich-quick scheme.

FROM THE VAULT

Let’s Connect!

Follow us for daily inspiration and deep dives: @GamedayGrails

Do you own a vintage-inspired sportswear brand we should be aware of? Reach out.

Have feedback, ideas or want to collab? Email [email protected] with any ideas, we’re usually down to clown.

Thank you for being part of the Gameday Grails family.