Last week, my mom called me in a panic. She was cleaning out my childhood closet in Chicago and found a shoebox with what she described as “an obscene amount of receipts.” She wasn’t wrong. I’ve kept every clothing receipt since college – a weird habit that started as tax write-offs for work clothes and morphed into some bizarre documentation project of my style evolution. “Should I throw these away?” she asked, clearly hoping I’d say yes. Instead, I had her overnight the box to me in Brooklyn. Look, I never claimed to be normal about clothes.
When the box arrived, I dumped the contents across my living room floor and spent an entire Saturday night (yes, on a weekend – judge away) organizing fifteen years of purchases by category, brand, and year. My roommate walked in around 11 PM, looked at me sitting cross-legged surrounded by tiny slips of paper, and just slowly backed out without saying a word. Smart man.
But here’s the thing – this weird little archive revealed something fascinating about what we call “investment pieces” in the menswear world. We throw that term around constantly. “Invest in quality!” “Buy less, buy better!” “This $1,200 jacket will last forever!” I’ve written those exact phrases in probably fifty different articles over the years. But my receipt graveyard told a different, more nuanced story about which expensive purchases actually earned their keep and which ones… well, which ones were just expensive mistakes with good marketing.
So I did something deeply nerdy – I calculated the actual cost-per-wear of everything I still owned from those receipts. And honestly, the results surprised me. The highest-priced items weren’t automatically the best values. Some trendy designer pieces I’d convinced myself were “investments” had terrible cost-per-wear ratios because I barely touched them after the initial honeymoon period. Meanwhile, some mid-range pieces had essentially paid for themselves hundreds of times over.
Let’s talk about the winners first. The single best investment piece in my entire wardrobe is – I’m not kidding – a navy merino wool crewneck sweater from Brooks Brothers that I bought on sale for $88 in 2012. I’ve worn this thing conservatively 30 times a year for eleven years straight. That’s 330 wears at minimum, making the cost-per-wear about 27 cents. The elbows have been patched twice by my tailor Miguel (who laughs every time I bring it in but respects the commitment). The color has barely faded. It’s traveled to six countries. I’ve worn it to work, to bars, on dates, to family Christmas, and once to a wedding when the airline lost my luggage.
My Alden plain-toe boots in brown calfskin ($595 in 2017) are approaching the 400-wear mark, bringing them down to about $1.49 per use – and they’re nowhere near done. I’ve had them resoled twice, and the uppers just keep getting better. In fact, almost all my footwear investments have paid off spectacularly well. My Allen Edmonds Park Avenues ($395) are at roughly $2 per wear after six years of regular rotation. Even my splurge purchase – Crockett & Jones loafers that cost a painful $675 – is down to about $4 per wear and dropping steadily.
On the jacket front, the results are mixed. My Barbour Beaufort waxed jacket ($415 in 2014) is crushing it at probably 80 cents per wear. But the trendy designer bomber I bought for almost $900 in 2019? I’ve worn it maybe 25 times total. That’s $36 per wear, and honestly, I probably won’t wear it much more because the style already feels dated. I was buying a moment, not a classic. Expensive lesson learned.
The pattern became clear: the true investment pieces share three core attributes – they’re functionally versatile, aesthetically timeless, and constructed to improve (or at least maintain) through years of use.
Take denim, for instance. The $65 Levi’s 501s I’ve had for four years have a better cost-per-wear ratio than the $285 Japanese selvedge jeans I splurged on around the same time. Why? The Levi’s fit better, feel more comfortable, and honestly, look better on me. The expensive jeans are objectively “nicer” in terms of fabric and construction, but if I don’t reach for them often, the math doesn’t work.
This leads to my first counter-intuitive finding: personal fit and comfort always trump quality on the investment hierarchy. An impeccably made garment that you don’t wear is always a worse investment than a good-enough garment that you reach for constantly.
My second finding: truly dependable investment pieces typically come from manufacturers who are specialists, not fashion houses. Alden makes boots and shoes, nothing else. Barbour built their reputation on waxed jackets. Schott is known primarily for leather jackets. The common thread is focus – these companies have been refining essentially the same products for decades or even centuries. They’re not chasing trends; they’re perfecting icons.
My third observation is that the sweet spot for most investment pieces isn’t at the luxury price point – it’s in the premium-but-attainable range. The difference in quality between a $100 sweater and a $300 sweater is usually significant. The difference between a $300 sweater and a $900 sweater is often just brand positioning and diminishing returns.
The absolute worst investments, according to my receipt archaeology? Anything ultra-trendy, anything I bought for a specific event and never wore again (looking at you, aggressively patterned sport coat I wore to exactly one Kentucky Derby party), and—this one hurts—anything I bought on final sale without trying on first.
So what are the actual investment pieces that have proven their worth in my wardrobe? Here’s my definitive list based on real-world cost-per-wear:
Dark indigo jeans from a quality manufacturer (Levi’s, honestly, wins on value)
Plain-toe brown leather boots from a heritage shoemaker
Black or brown cap-toe oxfords (Allen Edmonds is the value sweet spot)
A navy wool suit with a natural shoulder (I got mine from Suit Supply, no regrets)
A gray or navy merino crewneck sweater (doesn’t need to be cashmere)
A waxed cotton jacket (Barbour is still undefeated here)
White Oxford cloth button-downs (Brooks Brothers still makes the best, fight me)
A navy blazer with minimal structure (J.Crew’s Ludlow was my gateway drug)
Plain-front chinos in khaki or olive (Save Khaki makes my favorites)
A simple leather weekend bag (mine’s from Filson, approaching 15 years of service)
Notice what’s missing? Statement pieces. Extremely of-the-moment designs. Anything with prominent logos or distinctive patterns that could date themselves. Most of my true investment pieces barely register to the average observer – they’re not flashy or immediately identifiable as expensive. They just quietly do their job, year after year.
This doesn’t mean never buy anything fun or trendy! God, that would be depressing. I still pick up seasonal pieces that probably won’t be in rotation five years from now. But I don’t delude myself that they’re “investments” – they’re entertainment expenses with a clothing category code.
The receipt box also revealed my dumbest repeated mistake: buying the almost-right version of something because it was on sale, then eventually buying the exactly-right version at full price later. I’ve done this with approximately… let me check the receipts… seven different navy blazers. If I’d just bought the right one first, I’d have saved hundreds. Lesson: sales aren’t savings if they lead you to compromise.
I realize this whole analysis makes me sound like a spreadsheet with arms, but there’s something liberating about knowing which supposedly “smart” purchases actually paid off and which ones were just expensive mistakes with good marketing. It’s changed how I shop, how I write about menswear, and frankly, how I judge my own closet.
Last month, I was eyeing this gorgeous camel hair topcoat that cost roughly the same as a decent used motorcycle. I had all the justifications lined up – timeless design, heritage brand, classic color that goes with everything. But then I thought about my actual life. How often would I wear a statement topcoat in New York, where subway platforms are sweltering even in January and I’m constantly running between meetings getting sweaty? Maybe 20 times a year, if I’m being optimistic. Even if I kept it for ten years, that’s 200 wears – still putting the cost-per-wear higher than almost anything else in my wardrobe.
I passed. Instead, I put the money toward a week in Maine this summer. No regrets – though I did pick up a new pair of boots while I was there. Some habits die hard.
So the next time some menswear pundit (myself included) tries to tell you that some astronomically priced garment is an “investment,” ask yourself: will you actually wear it 100+ times? Does it fit seamlessly into your real life, not your imagined fancy life? Is it made by a company with a track record of durability? And most importantly – do you actually love it enough to reach for it year after year? If not, it’s not an investment; it’s just an expensive purchase. And that’s fine too, as long as you’re honest about it.
Now if you’ll excuse me, I need to go put on my ancient Brooks Brothers sweater and get back to work. At 27 cents per wear and counting, I’m practically being paid to wear it at this point.
