I Spent a Year Obsessively Tracking Every Piece of Clothing I Bought (The Results Were Brutal)

It started with me standing in my tiny SF apartment at 2 AM, staring at another Amazon package I’d apparently ordered but couldn’t remember. Was it the gray henley? Another pair of dark jeans? Honestly, I had no clue. My credit card statement was… well, let’s just say it was getting embarrassing. Here I am, supposedly this minimalist wardrobe guy who writes about intentional purchasing, and I was basically shopping like someone having an extended identity crisis.

The wake-up call was realizing I’d bought three nearly identical navy t-shirts in two weeks. Three. Of the same shirt. Because apparently my brain just shuts off when I see “30% off” in an email subject line.

So I did what any engineer would do when faced with a problem—I decided to track everything. Every single clothing purchase for an entire year. Not just what I spent, but where I bought it, why I thought I needed it, and most importantly, how much I actually wore it. My girlfriend thought I’d finally lost it completely. “You’re going to spreadsheet your wardrobe?” Yeah, basically.

The system was simple but required serious dedication. Every item got logged immediately—date, description, price, store, and what I called my “justification category.” These ranged from practical stuff like “replacing worn out item” to the more honest “saw it on Instagram and got weird FOMO.” I also created a category called “optimistic lifestyle purchase” for items bought for a version of me that doesn’t actually exist.

Then came the tracking part. I put tiny dots on clothing tags and noted every single wear in my phone. Sounds obsessive because it absolutely was, but after a few weeks it became automatic. Standing in the bathroom each morning, picking out clothes, making a quick note. My coworkers definitely thought I was having some kind of breakdown.

Twelve months later, I had data on 97 purchases totaling… Christ, I don’t even want to say the number. Let’s just say it was more than my rent for several months. But the real shock wasn’t the total—it was how little I actually wore most of this stuff.

Ready for the brutal truth? I wore only 38% of my new purchases more than ten times. More than half sat in my closet basically untouched. That expensive Japanese denim I convinced myself would be my “everyday jean”? Worn exactly four times because they were too stiff and uncomfortable. The olive green chinos that looked great in the store lighting? Turns out they made me look like I was cosplaying as a park ranger.

The worst category was what I labeled “fantasy lifestyle purchases.” You know those items you buy for the person you think you might become? The linen button-down for all those outdoor brunches I never attend. The wool bomber jacket for my nonexistent weekend trips to wine country. The leather Chelsea boots for… I honestly have no idea what I thought I’d do in leather Chelsea boots in San Francisco.

These fantasy purchases ate up 24% of my annual clothing budget while delivering maybe 5% of my actual wear time. I was basically funding a costume department for an alternate universe version of myself who’s way more social and lives somewhere with actual seasons.

But it wasn’t all depressing financial self-awareness. Some clear patterns emerged about what actually worked.

The boring basics absolutely destroyed everything else in cost-per-wear. Plain white and gray t-shirts from Uniqlo got worn 40+ times each. My two pairs of Levi’s 511s in dark indigo averaged 58 wears. A simple navy crewneck sweater from Everlane hit 73 wears, making it roughly 41 cents per use. Not exactly Instagram-worthy, but incredibly practical.

Here’s what surprised me about dress shirts—the sweet spot wasn’t where I expected. The really expensive ones ($200+) barely got worn because I was “saving them for important meetings” that never seemed important enough. The cheap ones ($40 and under) looked like garbage after a few washes. But the mid-range options from brands like Proper Cloth and Taylor Stitch? Those got consistent rotation and held up well.

My biggest shock was in footwear. I’ve always been a shoe guy—it’s my weakness, probably because my dad drilled into me that “you can tell everything about a man from his shoes.” I assumed my expensive minimalist sneakers and handmade leather boots would be the workhorses. Wrong. A pair of absolutely basic Adidas Stan Smiths racked up 89 wears, while the $300 Italian leather boots I’d lusted after for months sat at 12 wears. Why? Simple comfort. Turns out I consistently choose what won’t make my feet hurt during long days walking around the city, regardless of how cool they look.

The wild cards were interesting too. A bright yellow rain jacket I almost returned because “it’s not really my style” ended up with 34 rainy day wears and got more compliments than anything else I bought. A vintage Pendleton shirt from a thrift store in Oakland became one of my most-worn pieces, beating out options that cost ten times as much.

The data also revealed my absolute worst shopping triggers. Travel was the big one—I spent an average of $280 before every work trip on stuff I convinced myself I “needed.” That weekend in Portland? Apparently required new shoes. The conference in Austin? Somehow demanded three new shirts. None of this made any sense in retrospect.

I also discovered specific price ranges that triggered completely different behaviors. Under $50, I barely thought about purchases and often ended up with duplicates of things I already owned. The $50-120 range was dangerous territory—expensive enough to feel like a treat but not expensive enough to really consider. Most of my regrettable purchases fell here. Above $150, I actually did research and generally made solid choices, though sometimes I overthought things to death.

The timing factor was huge too. My worst purchases invariably happened under pressure—last-minute needs before events, rushed lunch break shopping, late-night browsing after a few beers. Every single item I labeled “what was I thinking?” came from pressured circumstances.

Meanwhile, the pieces that worked best were ones I’d considered for weeks or months. Items I’d tried on multiple times, left the store without buying, then returned for when I couldn’t stop thinking about them. Time turned out to be the best predictor of purchase satisfaction.

So what changed after this year of obsessive tracking? I implemented a mandatory 72-hour waiting period for anything over $75. Goes on a list, can only buy it after three days if I still want it. This alone cut impulse purchases by about 65%.

I started doing “wardrobe rehearsal“—trying potential purchases with at least three existing items before buying. If I can’t see multiple realistic combinations, it doesn’t come home. I deleted shopping apps from my phone and unsubscribed from sale alerts, which were clearly just impulse buy triggers.

I also run monthly “orphan checks”—identifying items that haven’t been worn in 30 days and either forcing myself to wear them immediately or admitting they were mistakes and donating them.

Has this made me perfectly rational about clothes? Hell no. Just last month I bought a vintage Carhartt jacket I absolutely didn’t need because I’d been watching too many workwear Instagram accounts and briefly convinced myself I was some kind of rugged craftsman instead of a software engineer who complains when the office WiFi is slow.

But the numbers don’t lie. In the eight months since my official tracking ended (though I’m still doing it because apparently this is my life now), total spending is down 67% while satisfaction with new purchases has gone way up. The success rate—items worn 15+ times in the first three months—jumped from that depressing 38% to a much healthier 81%.

The biggest benefit hasn’t been the money saved, though my bank account appreciates it. It’s the clarity about my actual lifestyle versus the fantasy version I was shopping for. I finally understand my real patterns and the environmental factors that lead to stupid decisions.

For someone who supposedly helps other people build better wardrobes, it was a necessary reality check. I had to admit I wasn’t following my own advice about intentional purchasing. But now I have data backing up what actually works versus what I think should work.

My closet is smaller, more functional, and everything in it actually gets worn. My girlfriend still thinks the tracking system is weird, but she admits my clothes fit better into our shared space now. I’d call that progress.

Yeah, I’m fully aware that creating an elaborate spreadsheet to track clothing purchases is objectively insane behavior. But at least I got some good data out of it, and my bank account has stopped sending me those concerned “unusual spending pattern” notifications.