Three weeks ago, I was helping my parents clean out their garage in Sacramento and found this old shoebox stuffed with receipts I’d been hoarding since college. Yeah, I know – keeping every clothing receipt for over a decade is probably certifiably insane, but hear me out. It started as a way to track tax deductions for work clothes, then somehow turned into this weird documentary project of my journey from tech-bro-in-hoodies to someone who actually cares about what he wears.
My mom was ready to toss the whole box, but I convinced her to ship it to my SF apartment instead. When it arrived, I dumped everything onto my kitchen table and spent an entire Saturday night (don’t judge) calculating cost-per-wear on every single purchase I still owned. My girlfriend walked in around midnight, saw me surrounded by tiny receipts with a calculator and spreadsheet, and just said “This is why people think engineers are weird” before going to bed.
But here’s the thing – this nerdy exercise completely destroyed my assumptions about “investment pieces.” You know how we’re always told to “buy quality,” “invest in classics,” and “spend more on things that last”? I’ve literally written blog posts using those exact phrases. Turns out the real math is way more interesting than the marketing.
The biggest revelation? Price doesn’t automatically equal value. Some of my most expensive purchases had terrible cost-per-wear ratios because I barely wore them. Meanwhile, some mid-range pieces had essentially paid for themselves through sheer frequency of use.
The undisputed champion of my wardrobe is this navy merino crewneck from Everlane that I bought for $68 in 2020. I’ve worn this thing at least twice a week for four years – that’s roughly 400+ wears, making the cost-per-wear about 17 cents. It’s traveled with me to three different jobs, survived countless washes, and still looks basically new. I’ve worn it to client meetings, coffee dates, my cousin’s wedding (under a blazer), and probably half the Zoom calls of the pandemic era.
My Common Projects Achilles sneakers tell a similar story. Yeah, $400 for white leather sneakers sounds insane when you say it out loud, but I’ve worn them probably 250 times over three years. That’s $1.60 per wear and dropping. They still look great, age beautifully, and work with everything from jeans to tailored trousers. Compare that to the trendy chunky sneakers I bought for $180 last year – I’ve worn those maybe 15 times because they already look dated. That’s $12 per wear for shoes I’ll probably donate soon.
The footwear category generally performed well in my analysis. My Red Wing Iron Rangers ($320) are approaching 300 wears over five years, putting them at just over a dollar per use. Even my “splurge” purchase – Paraboot loafers that cost a painful $450 – is down to about $3 per wear after two years of regular rotation.
Outerwear was more hit-or-miss. My Patagonia Better Sweater ($99) is absolutely crushing it at maybe 50 cents per wear after four years of San Francisco fog duty. But that designer bomber jacket I convinced myself was an “investment” at $650? I’ve worn it exactly 18 times. That’s $36 per wear for something I barely touch because it feels too try-hard for my actual life.
The pattern became obvious: the best “investment” pieces share three qualities – they fit seamlessly into your real lifestyle, they’re made well enough to improve with age, and they’re aesthetically simple enough to never look dated.
Here’s what really surprised me though – personal fit matters more than objective quality. I have this pair of $45 Uniqlo chinos that I’ve worn probably 200 times because they fit me perfectly and feel great. Meanwhile, those $150 “premium” chinos from a heritage brand? Maybe 20 wears total because the rise is wrong for my body type. Better construction means nothing if you don’t reach for the item.
Another insight – the sweet spot for most categories isn’t at the luxury price point. It’s in that premium-but-reasonable range. The difference between a $50 t-shirt and a $150 t-shirt is usually significant. The difference between a $150 t-shirt and a $300 t-shirt? Often just marketing and diminishing returns.
The absolute worst performers in my cost-per-wear analysis? Anything I bought for a specific occasion (that $200 holiday party shirt I wore exactly once), anything ultra-trendy that dated itself quickly, and – this one stings – anything I bought on sale without trying on first because “it’s such a good deal.”
Looking at the receipts also revealed my dumbest repeated mistake: buying the almost-right version of something because it was cheaper, then eventually buying the actually-right version later. I’ve done this with white sneakers, navy sweaters, and khaki chinos. If I’d just bought the right thing first, I’d have saved hundreds.
So what are the actual investment pieces that proved their worth? Based on real math from my own closet:
Well-fitting dark jeans from a solid brand (my Levi’s 511s are undefeated here)
Simple white leather sneakers (Common Projects or similar)
Brown leather boots with a classic silhouette (Red Wing, Thursday, or similar)
A navy merino sweater without any fancy details
White and light blue button-down shirts (I like Everlane and Uniqlo)
A versatile zip-up hoodie or cardigan (sounds basic, but gets constant wear)
Olive or khaki chinos that actually fit your body
A simple navy blazer that works with jeans
Basic t-shirts in white, gray, and navy (I buy multiples when I find ones that fit well)
A decent leather belt in brown and black
Notice what’s missing? Logo pieces, statement items, anything too fashion-forward, or anything that screams “expensive” to casual observers. My best investment pieces are basically invisible – they just quietly do their job year after year without drawing attention to themselves.
This doesn’t mean I never buy anything fun or trendy anymore – that would be incredibly boring. But I don’t pretend those purchases are “investments.” They’re entertainment expenses, and that’s totally fine as long as I’m honest about it.
The receipt analysis completely changed how I shop. Last month I was eyeing this gorgeous wool coat that cost about the same as a nice vacation. I had all the justifications ready – timeless design, heritage brand, classic color. But then I thought about my actual life in San Francisco, where I work from home three days a week and the weather rarely requires serious outerwear. Maybe I’d wear it 15 times a year? Even keeping it for a decade, that’s still terrible cost-per-wear compared to everything else in my closet.
I passed on the coat and put the money toward upgrading my home office setup instead. Way better use of funds for my actual lifestyle.
This whole exercise taught me that the menswear world’s obsession with “investment pieces” often misses the point. The real question isn’t whether something is well-made or from a prestigious brand. It’s whether you’ll actually wear it enough times to justify the cost. My $68 Everlane sweater is a better investment than most people’s $500 designer pieces because I reach for it constantly.
The math doesn’t lie – frequency of wear trumps everything else when it comes to value. A moderately priced item you love becomes an incredible deal over time. An expensive item you rarely touch is always a waste of money, no matter how “classic” or well-constructed it is.
Now if you’ll excuse me, I need to go put on my cost-per-wear champion sweater and get back to optimizing my wardrobe like the engineering nerd I am. At 17 cents per wear and counting, it’s practically paying me to wear it at this point.
Ruth lives in San Francisco and swears by “fewer, better things.” His posts explore minimalist wardrobes, quality basics, and dressing intentionally without turning fashion into clutter. Practical, efficient, and quietly stylish—just like his closet.
