I’ve got to tell you, I’ve heard the investment pitch more times than I can count. You know the one – some earnest salesperson at Bergdorf’s or Barneys (back when it existed) looking you dead in the eye and explaining how that $2,400 Isaia suit isn’t really an expense, it’s an “investment.” The cost-per-wear math, the generational durability, the whole song and dance. Hell, I bought into it myself for years. Margaret used to roll her eyes when I’d come home with another “investment piece” that would supposedly pay for itself over time.
But here’s the thing – after a quarter century of accumulating what I was told were investment-grade menswear pieces, I started actually tracking what happened to their values. The results were… well, let’s just say they didn’t match the sales presentations. That gorgeous Kiton suit I convinced myself was an heirloom? Tried to consign it last year and nearly choked on the offer. The “investment-grade” Hermès tie collection? Don’t even get me started.
So I got curious. Really curious. Started digging into auction records, talking to vintage dealers, tracking secondary market prices. What I found challenged pretty much everything I thought I knew about valuable menswear. Turns out there really are pieces that hold or increase their value – they’re just not what you’d expect, and they’re definitely not what most retailers are pushing as “investments.”
Let me be clear upfront – buying clothes as financial investments is generally terrible strategy. You’d be better off putting that money in an S&P 500 index fund and shopping at Jos. A. Bank. But if you’re like me and you love the intersection of style and collecting, there are legitimate categories where smart purchases can maintain or grow their worth while you actually wear them.
The brutal truth about traditional luxury menswear? It depreciates faster than a new BMW driving off the lot. That hand-stitched Brioni with the perfect shoulder line? The cloud-like Loro Piana cashmere? The meticulously crafted Edward Green shoes that cost more than some people’s mortgage payments? All spectacular products that might outlast you with proper care, but their secondary market value drops 50-70% the moment you cut the tags off.
I learned this lesson the expensive way when I tried selling a barely-worn Brunello Cucinelli sport coat a few years back. Original price made my accountant wince. Consignment offer made me question my life choices. The painful reality is that even the finest ready-to-wear luxury menswear follows the same depreciation curve as any other consumer good, just starting from a higher altitude.
But here’s where it gets interesting – certain categories buck this trend completely. The strongest performers, surprisingly, are limited production boots and shoes from makers with cult followings. Not the ones you’d expect, either. Those Edward Green shoes I mentioned? Beautiful, but they don’t hold value like you’d think. The real winners are brands like Viberg, the Canadian bootmaker whose limited releases sell out in minutes and routinely resell for 20-40% above retail.
I’ve been tracking this for five years now. A pair of their “Matte Black Calf” service boots from 2017 that retailed for $720 just sold on Grailed for $1,100. That’s essentially 8% annual appreciation on something you can actually wear. Compare that to my Edward Green collection, which would probably fetch 40% of what I paid if I’m being honest.
The magic ingredient seems to be artificial scarcity combined with passionate collector communities. Certain Alden limited editions follow the same pattern. Their collaborations with specialty shops – Leffot, Brick+Mortar, The Bureau Belfast – have proven consistently valuable. The most collectible are their shell cordovan pieces in rare colors like “Cigar” and “Ravello,” which use increasingly scarce light brown shell. A collector I know in Boston has seen his collection of rare Alden models appreciate roughly 80% over six years. Not bad for shoes he actually wears to work.
Moving to leather jackets – vintage American pieces from makers like Schott, Aero, and Langlitz have been quietly appreciating for decades. A 1950s Schott Perfecto that would have cost maybe $30 originally (call it $400 in today’s money) now commands $1,500-2,000 in excellent condition. Even contemporary pieces from certain artisanal makers hold their value remarkably well. Ten C’s limited pieces typically maintain 80-90% of retail years later.
The wildcard here is Bode’s one-of-a-kind pieces, which have shown genuine appreciation. Those hand-embroidered leather jackets that retailed for $2,000-2,500 three years ago are now selling for $3,500+ on the secondary market. Whether this reflects lasting value or just current hype remains to be seen, but Emily Bode’s pieces have certainly outperformed traditional luxury in terms of value retention.
Denim presents the most fascinating case study. Regular production jeans, even from prestigious Japanese selvedge makers, lose value immediately then stabilize around 60-70% of retail. But certain limited collaborative releases? Different story entirely. Iron Heart’s “25oz” anniversary series has appreciated 50-100% depending on the model. Original Warehouse Japan “tonal” stitched jeans from the early 2000s now sell for 2-3x their original price. We’re talking about jeans that cost $300-400 originally now commanding $800-1,200 in worn but well-maintained condition.
The pattern seems to be tied to cultural moments in menswear history. When brands close, when production methods change, when key figures leave – the products from these transitional periods often appreciate significantly. It’s not just about quality (though that matters), it’s about capturing something that can’t be replicated.
Watches are obviously well-known investment vehicles, but the accessible end is more interesting than the Rolex headlines suggest. Certain Seiko limited editions have tripled in value over the past decade. Universal Genève chronographs from the 1960s show steady 10-15% annual appreciation. Even certain Swatch artist collaborations from the 1980s now command serious money – a Keith Haring Swatch that sold for $50 in 1986 recently traded hands for over $7,000.
The common threads across all these categories are remarkable. Limited production is essential but not sufficient. Cultural significance matters enormously – items that embody particular moments in menswear history appreciate far more than technically superior products without that resonance. Craft processes that can’t be replicated drive value. When skilled artisans retire, when techniques become uneconomical, when source materials disappear, the products from these windows often see significant appreciation.
Documentation matters too. The leather jacket with proof of celebrity provenance, the suit with measurements for a famous politician – these stories create value beyond intrinsic quality. I’ve seen ordinary garments command extraordinary prices simply because they came with the right paperwork.
The most surprising finding? Price point has little correlation with investment potential. Some of the strongest performers started at accessible prices, while many ultra-luxury items depreciate catastrophically. That $300 pair of Japanese jeans might outperform a $3,000 Neapolitan suit jacket as an investment.
What does this mean practically? First, stop pretending your regular clothing purchases are investments. They’re expenses – hopefully worthwhile ones that bring quality and pleasure to your life, but expenses nonetheless. I’ve made peace with this. That beautiful Isaia suit serves me well in depositions and client meetings. The fact that it’s worth a fraction of what I paid doesn’t diminish the confidence it gives me or the compliments it generates.
But if you’re passionate about specific categories and learn their nuances deeply, there are opportunities to wear beautiful things that maintain reasonable value. My strategy has evolved toward what I call “neutralizing” rather than investing – focusing on pieces I genuinely love that happen to have characteristics suggesting they’ll hold value.
This means researching limited releases, understanding production constraints, learning about makers’ histories and when they changed key processes. It means following auction results and secondary market prices. It’s work, frankly, but if you enjoy the research process (and I do), it can add another dimension to collecting.
The most successful collectors I’ve talked to share a philosophy – they buy what they love and understand deeply, with appreciation being a pleasant surprise rather than the primary goal. The retired investment banker I know with his incredible shell cordovan collection didn’t set out to build appreciating assets. He simply fell in love with Alden’s aesthetic and quality. That his collection is now worth substantially more than he paid is bonus to the decades of enjoyment they’ve provided.
Maybe that’s the real insight here. The best investment in menswear isn’t financial but experiential. The garments that give you confidence, pleasure, and functionality provide returns no spreadsheet captures. If they maintain some value along the way, consider it found money – like discovering a forgotten twenty in last winter’s coat pocket, hopefully with more zeros attached.
I still buy beautiful clothes that depreciate immediately. Still love my tailored suits despite their terrible resale value. Still think a well-made shirt is worth paying for even knowing I’ll never recoup the cost. But now I also own a few pieces that happen to be appreciating while I wear them, and I won’t lie – there’s something deeply satisfying about that combination of utility and value retention.
The investment pitch will continue, of course. Salespeople will keep explaining how that $1,500 jacket is really an heirloom piece. But now I know which items might actually live up to those promises, and more importantly, which ones never will. It’s made me a more thoughtful buyer and, paradoxically, freed me to enjoy beautiful things without the pressure of justifying them as investments.
Arthur’s a Philadelphia attorney who believes good tailoring never goes out of style. He writes about craftsmanship, proper fit, and the quiet confidence of classic menswear. His posts champion tradition over trends and remind readers that true style is built on respect—for clothes, and for yourself.
