Two weeks ago I was cleaning out my parents’ garage in Sacramento and found myself weeding through a shoebox full of receipts. Old receipts I’ve been hoarding since college. Ok ok plug plug judge me for #receiptgate but let me explain.
I started keeping receipts to track work clothing deductions, but they ended up becoming a little time capsule documenting my journey from tech-bro-in- hoodies > lazy-dude-in-t-shirts > trying-to-care-about-fashion-things adult. If my mum had her way she would’ve tossed that shoebox long ago but lucky for me I had her ship it all the way to my flat in SF. I emptied that shoebox onto my kitchen table and spent an entire Saturday night (yeah… sue me) calculating cost-per-wear on every item I still own from that god forsaken shoebox.
As I was jotting down notes on each items purchase price with a highlighter my girlfriend walks in around midnight seeing me drown in a pile of folded receipts armed with only a calculator and an Excel spreadsheet. She laughed, shook her head and said “This is why people think engineers are weird” and went back to bed.
But shit man, digging through +10 years of purchases really gave me a newfound perspective on how most people misunderstand “investment pieces.” How many times have we heard people tell us 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 sentiments.
But when I sat down and did the math on my own closet the actual numbers told a completely different story. Mind. Blown.
Turns out expensive clothes don’ t always equate to “best value.” Some pretty penny items I bought actually had horrible cost-per-wear ratios because I just ended up wearing them way less than I thought I did. Other budget buys were worn so much they practically paid for themselves. Hands down winner of all winners in my wardrobe?
This baby right here. Navy crewneck made from 100% merino wool by Everlane I picked up in 2020 for… wait for it $68. Man this jumper… I can’t even begin to explain how many times I’ve worn this thing.
Conservatively I wear it twice a week, which means this bad boy has been worn over 400 times. That’ s right – 400+ wears at $68 bucks. That puts its cost per wear at 17 cents. We salute you Champion jumper.
You’ve been to 3 different jobs with me, multiple countries, worn with shirts, jackets, jumpers on top, washed so much your probably half way through your lifespan and still look like new. Client meetings > coffee dates > wedding (under a blazer) > pretty much every zoom call of the pandemic… you name it I’ve worn it with this jumper. My White Common Projects Achilles are another story of the same calibre.
Who honestly wakes up and says “ Yeah I know! I’ ll spend $400 on some white trainers today.” Any other brand name and you’ re looking at half that price. BUT hear me out.
I’ve worn mine almost 250 times in just under three years. That puts cost-per-wear at $1.60 and counting. They still look brand new ( CP ages like a dream ), are versatile enough to go with jeans, chinos, dress trousers you name it… and WILL last me a decade.
Compare that to the trendy Yeezy’ s I dropped 220 bucks on last year….I probably wore those trainers 25 times total. They already look dated to me at this point. 25 wears at $220 equals $9 cost per wear.
I will probably donate these within the next year. Same story with clothes as footwear. My Red Wing Iron Rangers were $320 but are on pace to hit over 300 wears by the end of this year.
Thats just slightly over $1 each time I put those on. I spent more than I wanted too on those Paraboot loafers at $450 but because I wore the shit out of them for the last two years they’ re down to $3 wear. My Patagonia Better Jumper has been worth every penny of that $99 price tag after 4 years of wear.
We are talking maybe $.50 per wear and those stupid things still look new. But that $650 designer jumper I swore I’ d wear all the time? 18 total wears. $650/18 = $36 each time I wore that thing.
Which I basically refuse to wear now because it just feels like I’ m trying too hard. Why do these items get worn more than others? 3 simple reasons. They fit your lifestyle. When choosing an investment piece ask yourself “ will I wear this?” I see too many people buy trendy items they think they should wear, but end up hanging in their closet. You can actually see yourself wearing the item multiple times a week.
NOT once every other month. The item is well made enough to actually look better with age. There is nothing worse than a “quality” item that looks new but has already lost it’ s shape. Lastly, and most important… they’ re basic enough that they don’ t ever go out of style. If I can’ t see myself wearing it 5 years from now when it comes to trends… I don’t buy it. TLDR – The true “investment” is spending your money on items that suit your lifestyle. Not what blogs and instagram tell you is “worthy” of spending money on. The real kicker is … How well an item fits you is MORE important than how good of an item it actually is. Fact for all you cheapbillies out there buying that $450 pair of boots because “it’s supposed to last you forever.” If that button falls off every time you sit down because of your whopping inseam then you ain’t gonna wear those boots.
They’ ll sit in your closet and gather dust. An item can be made with all the fancy Korean thread count fabric but if it’ s not YOUR SIZE it’ s not worth it. Lesson learned – fit matters more than you might think.
I have an inexpensive pair of $45 Uniqlo chinos I wear CONSTANTLY and have worn close to 200 times because they actually FIT like a glove and feel amazing on my body. Compare that to that $150 “better” version of the same style chino I bought from that super popular heritage brand. I’ ve worn them maybe 20 times because they just don’ t FIT my body right.
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No amount of thread count will fix bad fit. Another hard lesson I learned through this.. For most clothing categories, YOU DO NOT need to spend the “luxury price point.” Once you start crossing that threshold where prices grow exponentially the value you’ll get from that item doesn’ t increase at the same rate.
The jump between a $50 and $150 t-shirt is huge. but the jump between a $150 and $300 one? That my friends is just pure marketing and diminishing returns. Ask yourself how many times you’ll wear that item BEFORE you buy it.
You can easily toss that number into this handy dandy spreadsheet I made to estimate cost per wear. Shit, I even held myself accountable and calculated cost per wear on a bunch of my old purchases. Winner = Champion jumper.
Loser = My trendy ass tie-dye shirt I bought last summer and wore twice. My biggest shopping regrets?? Things I bought to wear for one specific occasion and ended up wearing once.
Onesies I bought “just because they were on sale.” ( hello ~ $200 Christmas party shirt I wore once ) And obviously whatever trendy item is popular when you read this. Moral of the story – Stop buying shit you don’ t need. Something else I learned when digging through old purchases?
I’m THE WORST at buying similar items because something was too expensive. I’ve wanted a pair of white trainers for YEARS but every time I go to buy them they are always $100 more than I want to spend. Instead of waiting and buying them I end up buying the cheaper $100 option.
Then halfway through trying to justify that cheap pair I forget about them and buy the $250 pair I originally wanted. If only I would’ve waited and bought that original pair I would have saved $150. White trainers are only one of many times this has happened to me.
Same story with navy jumpers and even khaki trousers. Next time before you buy that “close enough” item ask yourself if you wanted THAT item months ago why not now? Value vs Worth.
What are some “true” investment pieces that DO live up to the hype? After going through every single item in my closet I’ve found these to be my go-to’s year after year: -Dark jeans that FIT YOU REALLY WELL from a brand you trust ( my favourite are Levi’ s 511) -White leather trainers ( I love CP but there are options at literally every price point) -Brown leather boots that aren’ t trendy and will last you years. ( Think Red Wing, Thursdays, etc) -Solid navy merino jumper that doesn’ t have any “ extra crap” going on. -White and light blue button ups. ( I’m a stickler for Everlane and Uniqlo because they FIT) -Basic zip up hoodie or cardigan. ( I know boring af but I have three of each and wear them ALL THE TIME) -Olive or khaki trousers that don’ t look “like you’re about to stage a country music concert” and FIT YOUR BODY. -A plain navy blazer that goes with everything including your jeans. -Plain t-shirts in white, grey, and navy. (buy as many of these as you can when you find ones that FIT) -A decent leather belt. I like to own one brown and one black.
Notice how there isn’ t a single trendy thing, flashy item, or any “ haute couture ” rubbish on that list. The TRUE “investment pieces” are probably the ones nobody else will notice. But that’ s kind of the point..
They WORK. They do their job and will never go out of style. Now don’ t get me wrong, I still buy trendy things.
Heck we spend entire weekends trying on stupid clothes because we love “ playing dress up ” in my household. But I’ ve learned not to feel bad about those trendy items either. When I buy stuff I know I won’ t wear often I know I’ m buying them for fun.
They’ re like a hobby to me at this point. But I promise myself I WILL NOT delude myself into thinking they’ re “ worth it” or “ investment pieces.” I honestly can’ t tell you how much of a different shopper this has made me. Last week I almost bought myself this nice wool coat I saw online.
It would’ve been easy to justify too. Timeless cut, cool brand, neutral colour. But then I really sat down and thought about how often I’ ll actually wear that coat.
I work from home 3 days a week > it rarely gets that cold in San Fran where I need a coat > and on the days I do… do I NEED a wool coat? Probably 10-15 times a year? Clothes that are too expensive and you wear too little destroy your cost per wear.
If I wore that coat 3 times a week for 10 years….that’ s right. 300 total wears. Which is still significantly worse than everything else I own. So instead of ruining my own cost per wear I kept shopping and spent that money on my home office instead. Win win.
Choose the experience that suits your lifestyle. I know guyswear has had us hunting these “investment pieces” since we got our weirdos started on our style journey. Don’t get me wrong there are definitely items that are just better than others and worth spending more money on.
But before you throw down $500 on that new shirt.. see if you already have something that could fill that void.. Would you wear that $500 shirt more than my $68 Everlane jumper? If not why buy the expensive option?
To me that jumper is now THE investment because I know I’ ll wear it hundreds more times. There’ s a reason we put together that cost per wear calculator. Wear count matters more than you think when building out your wardrobe.
Sure that $450 shirt from the “ best brand ever ” will last you longer. But if you hate wearing that thing DOES IT REALLY MATTER if it lasts? Buy what you want to wear, not what you think you should wear. 🙂
