Two weeks ago I was moving boxes in my parents’ garage in Sacramento and stumbled upon a shoebox full of receipts. Old receipts I’ve been saving since college. Yeah yeah, go ahead <a href="https: //sartorialhim.com/i-tracked-every-clothing-purchase-for-a-year-the-surprising-data-on-what-was-worth-it/">judge me</a> for <a href="https://twitter.com/search?q=%23receiptgate" target="_blank">#receiptgate</a>, but hear me out. I started saving receipts to keep track of deductions for work clothes, but it turns into this time capsule of sorts chronicling my transformation from tech-bro-in-hoodies to lazy-dude-in-t-shirts to trying-to-care-about-fashion-adjacent-things adult.
My mom was about to throw it out but I had her ship it home to my apartment in SF. I emptied the shoebox on my kitchen table and spent a Saturday night (yeah… don’t judge) calculating cost-per-wear on every item I still own from that shoebox. As I was scribbling notes on each item’s purchase price with a highlighter, my girlfriend walks in around midnight and sees me in a sea of folded receipts armed with a calculator and an Excel spreadsheet. She simply laughed, shook her head and said “This is why people think engineers are weird” and went back to sleep.
But this little project of digging through 10+ years of purchases really opened my eyes on how most people misunderstand "investment pieces." How many times have we heard to "buy quality," "invest in the classics," and "spend more on things that last." Yup, I’ve even gone out of my way to write blog posts preaching those exact messages. And while there’s some truth to those ideas, the reality of the actual math tells a completely different story.
Surprisingly enough, expensive doesn’t always mean "better investment." Some high-dollar items I bought actually had atrocious <a href="https: //sartorialhim.com/the-athletic-brands-actually-worth-the-premium-prices/">cost-per-wear ratios</a> because I ended up wearing them so rarely. There were other not-so-fancy items I bought for much less that have essentially paid for themselves over how many times I’ve worn them.
Hands down winner of my entire wardrobe? This navy merino crewneck from Everlane I bought in 2020 for $68. I have worn this sweater more times than I can count – conservatively twice a week for the last four years. That’s right, this sweater has been worn over 400+ times making its cost per wear only 17 cents. It’s been to 3 different jobs, multiple countries, worn with all kinds of outfits, washed so many times it’s probably halfway through its life and still looks like new. Client meetings, coffee dates, wedding (under a blazer), and probably half the Zoom calls of the pandemic… you name it, I’ve worn this.
My Common Projects Achilles are a similar story. Who in their right mind pays $400 for white sneakers? Any other brand and you’re looking at half that price too. But I’ve worn mine close to 250 times in three years. That’s $1.60 per wear and falling. They still look brand new (CP ages so well), go with literally everything from jeans to chinos, and are built to last.
Compare that to the hype Yeezy’s I bought last year for $220… I’ve probably worn those 25 times because honestly they already look pretty dated to me. That’s $9 per wear on sneakers I will probably donate within the next year.
Sadly footwear wasn’t the only winner in my closet. My Red Wing Iron Rangers ($320) are closing in on 300 wears after five years. That’s just north of $1 per use. Even that overpriced pair of Paraboot loafers I drooled over for months and paid a ridiculous $450 for are down to about $3 per wear thanks to how frequently I’ve worn them for the past two years.
Outerwear was hit or miss. My Patagonia Better Sweater that I bought for $99 is crushing it at maybe $.50 per wear after rocking it for the last four years of SF fog duty. However my $650 designer bomber jacket I swore I’d wear all the time? I’ve worn it exactly 18 times. That’s $36 per wear for a jacket I basically refuse to wear now because it feels too much like I’m trying hard.
The common theme here is that your best "investment pieces" have 3 traits:
They fit your actual lifestyle.
They’re well made enough to look better with age.
They’re basic enough that they don’t ever go out of style.
BUT THE SHOCKER is…
How well an item fits you personally is MORE important than how objectively good the item is. Sure that $450 pair of boots from an acclaimed heritage brand will probably last you decades. But if that button is constantly falling off every time you sit down because of your wide legs, you’re not going to wear them. They’ll just gather dust in your closet. An item can be made with the highest quality materials and still be a complete waste if you don’t wear it.
Lesson I learned here is that great fit matters more than you might think. I have a pair of $45 Uniqlo chinos that I’ve worn probably 200 times because they actually fit really well and feel great. But those $150 "better" chinos I bought from that heritage brand? Maybe 20 total wears because they just don’t quite fit my body right. No amount of quality will make up for poor fit.
Another lesson – most clothing categories don’t justify spending the luxury price tag. Once you’re above a certain threshold the price increases way faster than the value you’ll get from the item. The jump between a $50 and $150 t-shirt is significant. The jump between a $150 and $300 t-shirt? Mostly marketing and diminishing returns.
The worst things I found in my cost-per-wear journey? Clothes I bought to wear for one specific occasion and wore once (hello $200 Christmas party shirt), trendy items that’ll date themselves, and
<insert massive pantsweater sweats closet nod> stuff I bought on sale without even trying it on first “because it’s such a good deal.”
Scrolling through old receipts also made me realize my most frequent shopping mistake: buying the close-but-not-quite-right product because it cost less, then later forgetting about that first item and buying the actually-right product. I’ve done this with white sneakers, navy sweaters, and khaki pants. If I had just waited and bought the right thing the first time I would have saved myself hundreds.
So what are true investment pieces that actually lived up to the hype? After crunching the numbers on my entire closet I’ve found these to be the items I reach for again and again year after year:
– Dark jeans that fit you really well from a brand you trust ( Levi’s 511 are my go-to)
– White leather sneakers (I’m partial to CP but there are options at every price point)
– Brown leather boots in timeless style (Red Wing, Thursday, etc)
– A solid navy merino sweater with no extra nonsense
– White and light blue button ups (I prefer Everlane and Uniqlo)
– Basic zip up hoodie or cardigan (sounds boring but I wear them all the time)
– Olive or khaki pants that don’t look “stage worthy” and fit your body
– A plain navy blazer that goes with your jeans
– Plain t-shirts in white, gray, and navy (buy multiples when you find ones that fit you well)
– A decent leather belt in brown and black
Notice how there’s nothing trendy, flashy, or stuff that “looks expensive” on that list. My most valuable "investment pieces" are probably the ones nobody else notices. But that’s kind of the point- they just work. They do their job and won’t ever go out of style.
This isn’t to say I never buy trendy things or fun fashion forward items anymore. I do! We have whole weekends dedicated to "broke ameture fashion blogger clothing hunts" in my household where we will try on all the silly clothes. But I don’t delude myself into thinking those clothes are "worth it" or "investment pieces." They’re fun as hobbies but that’s about it.
This experience has made me a completely different shopper. Last week I was coveting this beautiful wool coat I saw online. I could justify it easily too – timeless cut, prestigious brand, neutral color. But then I paused and thought about how I actually live in San Francisco. I work from home 3 days a week, it rarely gets cold enough here to where I need a coat, and when I do… do I really need a wool coat? Maybe 10-15 times a year? Expensive clothes bought too infrequently end up killing your cost per wear.
Even if I kept that wool coat for 10 years I’d only wear it about 150 times. That’s still way worse than everything else I already own. So I kept browsing and spent that money on my home office setup instead. Went with a much better experience for my lifestyle.
I realize now how obsessed the menswear industry has made us all about chasing "investment pieces." Buying things that are just objectively better doesn’t always mean you should buy them. Before you drop $500 on that new shirt spot check your closet and see if you have something that serves that same purpose you’re trying to fill. My $68 Everlane sweater is more of an investment than the bag sweater I’m currently lust crying over because I know I’ll wear it countless more times.
The math is there for a reason- how often you wear something matters more than price. A slightly expensive shirt you actually love becomes a steal over time. An ultra expensive shirt you hate wearing is never worth it no matter how fancy it looks or how well it’s made.
Alrighty I need to go throw on my champion sweater that’s single handedly paying for itself right now. At 17 cents per wear and counting I may as well wear it all the time.
