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An illustration of a pair of Nike sneakers in a vault Dennis Eriksson

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Menswear’s Best Financial Investments

Because you can’t Instagram your 401k.

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Financial advisors might tell you to make low-risk investments that will see your money grow slow and steady, but what if I told you it’s possible to buy clothing you love and still make a profit on the tail end? Come, step into my office.

Earlier this year, Baghunter reported that a Birkin bag is a safer investment than both gold and the American stock market (also known as the S&P 500). It’s hard to find such an exact comparison in menswear, but there are definitely certain items that, had you bet on them at retail, would be paying off handsomely right now.

For the person with the right eye and instincts, playing the clothing market is probably the most enjoyable get-rich-quick scheme. At least if things don’t work out, you have new clothes to wear, right? Besides, you can’t post sick Instagram photos of stock ownership and your 401k like you can a new pair of sneakers.

If you’re going to go this route, there are a couple things to know. According to Lucas Steuperaert, the menswear curator and editor at luxury resale site Vestiaire Collective, there are three characteristics that make an item a good investment: quality, desirability, and rarity.

He also notes that reselling items during times of designer change will get you the most value, like Hedi Slimane’s work at Saint Laurent. In that same vein (and to the surprise of no one), he suggests scooping up Alessandro Michele’s current Gucci designs and sitting on them. If you’re still not sure, the site recently launched a resale calculator that will do the thinking for you.

We looked into several different menswear categories to find out which items have a tendency to go up in value over time. These are the true investment pieces.

An illustration comparing the worth of a Raf Simons jacket and bars of gold Illustration by Dennis Eriksson


Clothing is one of the trickiest investments to make. Even the most desirable pieces struggle to retain their value, especially compared to bags and shoes, which appreciate better. This doesn’t mean there’s not gold in these here parts, though.

Here’s an example of one such success story: Raf Simons’s collaged fishtail parkas are a cornerstone of the designer’s work, and none are more iconic than the New Order-inspired “Power, Corruption, Lies” jacket from fall/winter 2003. We reached out to Raf Simons’s team, but they weren’t able to provide the exact retail price this sold for. The parka is the most expensive item to ever resell on Grailed, and the site’s brand director Lawrence Schlossman guesses it would have retailed for “1 to 2 Gs.”

We can assume that it would have sold at retail for roughly the same amount, $1,799, as a nearly identical Simons parka. The Power, Corruption, Lies, piece resold for $7,000 last year. That $5,000 profit results in a whopping 289% return on investment (ROI).

If you invested $1,799 in gold at the same time, when it was going for $417 an ounce, you’d have, with gold’s current market rate of $1,222 an ounce, $4,558 today. Someone remake that Austin Powers movie, stat.

Other items in this category don’t fare as well, though. The ready-to-wear item with the highest average resale value on Vestiaire is a Balmain biker jacket, which retails for $5,095. It resells for an average of “just” $2,700.

Heeding Steuperaert’s advice, let’s turn instead to really rare and hyped items, like a Supreme box logo T-shirt. According to Grailed, Supreme’s BOGO tees, which only cost $44 at retail, resell for an average of $202. That’s small change compared to the rest of these, but consider the fact that the investment is quadrupling in less time than it takes to stand in line and actually buy one.

The takeaway: Investing in clothing is hard, because you essentially have to hope that what you buy takes on some cultural significance that vaults the resell price into the upper echelon. The smart money is on limited-edition items from big-name brands or designers. Which, duh.

An illustration comparing watches to a 401k Illustration by Dennis Eriksson


Watches are slow burners. The ones that resell the best are no longer in production, were limited-edition from the get-go, and typically take ten to 20 years from the initial sale to hit their full potential, according to Bloomberg. Most of those are from historic brands like Rolex or Audemars Piguet.

The End of Days model from Audemars Piguet’s Royal Oak Offshore collection checks all the right boxes. Only 500 were made; it’s attached to a movie (End of Days) and its star, Arnold Schwarzenegger; and after ten years, its value appreciated greatly. It retailed in 1999 for $13,600 and resold for $85,000 in 2009. That’s a 525% ROI.

Compare that to something like a very safe 401k. If you invested $13,600 in a 401k and waited for it to mature over ten years, you’d get $26,753 — a 96.71% ROI.

However, this specific Audemars Piguet model is an outlier in the space. Rolexes retain their value well, but the key word there is retain. Vestiaire Collective reports that the top three watches in terms of average resale price are all made by Rolex: the Daytona (averaging $9,100 resale), the Submariner (averaging $5,500 resale), and the Datejust (averaging $4,000 resale). All those resale prices are below retail, though. The Submariner model, for example, originally sold on the very low end for $5,700.

The takeaway: While watches are the traditional items you’d peg for exactly this kind of experiment, a less classic option is actually the safer bet.

An illustration comparing a pair of Nike sneakers to a stack of cash Illustration by Dennis Eriksson


Sneakers have an enormous and immediate return on investment. The reseller market didn’t just grow out of nothing. Grailed reports that, on average, Kanye’s Yeezy 750s resell for $1,091, while the low-top 350s go for $668. (They cost $350 and $200 at retail, respectively.) Vestiaire reports that the more popular colorways eclipse even those numbers, like the Moonrock 350s, which resell for $1,200 on average.

Successfully buying Yeezys is a little like winning a scratch-off; it rarely happens, but when it does, the payoff is instant. However, it needs to be cashed in pretty quickly. As Grailed’s cofounder and head of marketing Jake Metzger told me in a separate conversation, “We've seen the price of Yeezys [in general] go down, I think due to the saturation of the market.” Reselling your Yeezys the day of release is the best move, because that’s when customers who missed out are most desperate.

Kanye’s collaboration with another company has left a more long-lasting impression. The rapper’s Nike Air Yeezy 2s have sold on eBay for practically all of Scrooge McDuck’s gold coins. A total resale value of $6,000 after only spending $245 for a pair of the sneakers in 2012 amounts to a ludicrous 2,757% ROI after only four years.

Even investing in Netflix, the best-performing stock in the past five years, according to SeekingAlpha, couldn’t match an investment in the Yeezys. In 2012, Netflix stock cost $8.09 a share. If you had bought $245 worth of it at that time, you’d be pretty happy with the stock’s current value of $124.34. But that still only equates to a current payout of $3,765.02, a bit over half of what the Nike Air Yeezys are worth.

The takeaway: Hyped-up sneakers are one of the safest investments and can provide instant returns, but holding on to the more iconic sneakers can lead to a huge payday.


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