10 NEW iconic investments you can literally put under the tree

Christmas is a time for joy, family, overeating, and pretending you have not checked the market since the second week of December. But if you are anything like me, the part of your brain that analyses investments never fully switches off. Last year, I channelled that energy into a playful piece called 10 iconic investments you can literally put under the tree.

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10 iconic investments you can literally put under the tree

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Readers loved it. They also immediately told me everything I had missed. Where were the rare books? The sneakers? The toy figures? One reader even insisted that an unopened iPod was a better investment than half the ASX 200.

Message received.

So this year I'm bringing it back, with 10 new physical assets that combine nostalgia, scarcity, cultural relevance and a surprising amount of investment potential. These are not recommendations, but they are real markets with real buyers and real price appreciation. And they all fit neatly under the tree.

Let’s unwrap them.

1. First-edition or signed rare books

There is something delightfully rebellious about gifting someone a book that could pay off their credit card. In a world full of screens, a first-edition novel feels like an artefact from a more elegant age when stories lived on paper and dust jackets were treasure.

Take a signed Great Gatsby. In the 1920s, it was a commercial flop. In 2024, a pristine signed copy sold for around US$450,000. The key factor in the high value is the original dust jacket, designed by Francis Cugat, which is both legendary and fragile, making unrestored copies exceptionally rare.

If you want a more current example, look no further than the Harry Potter books. The most expensive book is a first-edition, first-printing copy of Harry Potter and the Philosopher's Stone. Due to the extremely small initial print run in 1997, these rare copies have sold for record-breaking prices, with one copy fetching US$471,000 at auction in 2021.

That is the thing about culture. It appreciates quietly while no one is watching. And unlike some modern assets, you can display a rare book without anyone accusing you of joining a cult.

2. Limited-edition sneakers

If you had told your parents that one day people would keep shoes in temperature-controlled storage and trade them like mid-cap stocks, they would have laughed. Yet we now live in the golden age of sneaker investing.

Whilst the headline above says "limited-edition sneakers", that's really a synonym for Air Jordans - Michael, of course, started the whole movement, and a rare pair of J's remains the pinnacle of it. 

The record price for an Air Jordan 1 is US$560,000, set in May 2020 at a Sotheby's auction for a pair of game-worn, autographed sneakers from Jordan's rookie season. The sale, which coincided with the release of The Last Dance documentary, significantly exceeded its estimated value due to intense collector interest. 

Outside of older and game-worn sneakers, collaborations between brands with limited production runs can also fetch tidy sums. The Dior x Air Jordan 1 was a 2020 collaboration with an extremely limited production run of 8,500 numbered pairs worldwide. The sneakers initially retailed for US$2,000, which was high for a designer sneaker at the time, and were only available through a raffle held on the Dior website. Today, they would fetch around US$5000. 

Sneakers sit at the magical convergence of hype, scarcity and nostalgia. If not a game-worn pair, the rules are simple: keep them boxed, keep them clean and never, ever wear them. Wearing them is the sneaker equivalent of driving a classic Ferrari through a hailstorm.

3. Vintage toy figures

Everyone has a story about the toys their parents threw out. As it turns out, many of those toys are now worth five figures...and in some cases, much, much more. 

A sealed 1978 Luke Skywalker figure, which originally retailed for US$2.49, recently sold for US$161,458. Think that's crazy? Hold my beer. On August 18 last year, a 1979 Kenner Boba Fett action figure was sold for around US$1.34 million by Goldin Auctions. It is the most expensive toy/action figure ever sold, as well as the most expensive Star Wars item sold that wasn’t a prop.

Why do these toys command such prices? Because nobody kept theirs in the packaging. Toys were meant to be blasted by imaginary laser beams on the living room floor, not kept in museum-grade storage.

Collecting these today is essentially paying for the privilege of going back in time to tell your younger self: no, you cannot open that.

4. Hand-held Nintendo and retro consoles

Few gifts match the serotonin rush of unwrapping a Game Boy. It was a portal to a simpler universe where batteries died too quickly and everyone blew on cartridges even though it never helped.

Today, boxed original units are appreciating faster than some genuine tech stocks. These consoles are not toys anymore. They are time capsules. Buying one is basically placing a long-term bet on the enduring power of nostalgia. It has been an excellent trade so far.

5. Early-generation Apple devices

There was a time when unboxing an iPod felt like a lifestyle choice. Early Apple products were not just functional. They were designed to make people feel something.

That emotional pull has now become financial. In 2023, a sealed first-generation iPhone sold for US$190,373. Not because it is practical. It is not. But because it represents the moment the digital world pivoted.

These devices are the modern equivalent of vintage sports cars. They are also easier to store and far less likely to leak oil.

6. Retro computers and classic tech

The Apple II. The Commodore 64. The IBM 5150. These machines were the dawn of personal computing. They were clunky, beige and wonderful.

Collectors today do not care about utility. They care about history. They care about the satisfying click of mechanical keys and the glow of a CRT display. They care about the reminder that once upon a time, loading software was a 12-minute ordeal accompanied by loud static.

Like fine wine, these machines aged slowly, then suddenly became cool again.

7. Autographed sporting memorabilia

Some investments are financial. Others are emotional. Sporting memorabilia is both.

A signed bat or guernsey is not just ink on fabric. It is a moment frozen in time. A connection to greatness. A tangible reminder of why sport matters.

A signed and test-worn shirt of Shane Warne's recently sold for more than A$30,000. Nobody is paying for the cotton. They are paying for the story. And in the world of investing, story is often the scarce commodity.

8. Vintage Whisky

Whisky is one of the rare investments that rewards you even when it does not appreciate.

Collectors are chasing scarcity. Discontinued Macallans, old-label Yamazakis, legendary Hibikis that once gathered dust in duty-free shops and now command astonishing prices.

The most expensive bottle of Macallan is the Macallan Valerio Adami 1926, which sold for a record-breaking US$2.7 million at a Sotheby's auction in November 2023. This is one of just 12 bottles with a label designed by the artist Valerio Adami, from a total of 40 bottles produced from the 1926 vintage. 

Unlike wine, whisky does not age in the bottle. Supply only shrinks. Economics handles the rest. And if values do not rise, you still have yourself a very classy plan B.

9. Vintage cameras

Film cameras sit perfectly at the intersection of art, engineering and nostalgia. The Polaroid SX-70 is a design icon. The Leica M3 is as close to mechanical perfection as we may ever get.

Collectors are not buying them for resolution. They are buying them for romance. The tactile feel. The deliberate slowness. The imperfections that make analogue images feel alive.

In a world of infinite digital photos, true scarcity has value. These cameras have it in spades.

10. Classic magazines and original print issues

Magazines may seem disposable, but the right issue becomes cultural treasure.

A first-issue Playboy featuring Marilyn Monroe, graded 9.4, sold for US$120,000 in 2023. Early Rolling Stone covers are highly sought after. TIME covers from historic moments are instant nostalgia.

These are not just magazines. They are bite-sized pieces of history that fit perfectly under the tree.

Merry Christmas and happy investing

I made the point last year, but it is worth repeating because it sits at the heart of every great collection. When you are considering collectibles, make sure you love them first. Value comes and goes, markets rise and fall, and fashions twist in strange directions, but passion is the thing that endures. If you genuinely love what you own, you are far more likely to look after it, keep it in good condition, and hold on to it long enough for any potential appreciation to matter.

Collecting is at its best when it brings joy. The fact that some of these items might quietly appreciate in the background is simply the icing on the Christmas cake.

Merry Christmas, happy investing, and may your tree be filled with things that sparkle in both sentiment and value.