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I logged my entire wardrobe into a Clueless-style closet app

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It taught me not everything is worth optimizing

An image of Cher from Clueless tabbing over the app that allows her to plan outfits. Image: Paramount Pictures

When I tell people that I have my entire wardrobe uploaded to an iPhone app, I eagerly anticipate the response I’ll receive: Will they be curious and impressed by this digital masterpiece, or low-key aghast at my compulsive need to organize and categorize everything in my life? I’m never offended by the latter; in fact, I lean into it as I walk them through, in great detail, how the Stylebook app allows me to not only upload photos of each clothing item I own, but also tag the entries with the brand, size, cost, color, season, and more. But while I love showing off my digital closet, even to people who think the very concept is slightly unhinged, I don’t actually use Stylebook very much anymore. And yet I’ve never been happier with the app.

I downloaded Stylebook in 2015 as a way of helping me get a better sense of what I owned and how often I wore each item. I’m equally frugal and analytical, and I wanted to get data-based wisdom to help me determine which pieces were worth investing real money into instead of getting cheaper fast-fashion items that would likely fall apart within a year.

I spent weeks — OK, months — getting my Stylebook closet ready to use. This involved taking photos of the 200-some clothing items and pairs of shoes I owned, manually erasing the background in each picture, and then inputting facts and descriptors for each piece (Sorel boots: black, size 6, waterproof, $80; 1861 sweater: gray, size small, very cozy, $73). These literal and aesthetic labels helped me track my purchasing habits and spot trends across my closet. The app’s Style Stats section even turned this information into graphs visualizing the breakdown of colors, price points, and brands that make up my wardrobe.

A few of the statistical breakdowns of my wardrobe. Aren’t they beautiful?
Image: Apple Store via Polygon

Then, I built folders grouping the items by type and created tags to easily surface options for what to wear to a specific event, like a job interview or wedding. I created packing lists for upcoming trips and put together outfits without the bother of trying things on, saving my favorites to the app and ultimately saving me a lot of time. Sometimes, I’d even plan out my outfits a week in advance, taking the weather forecast and any social engagements into consideration.

Every day for years, I’d wake up and log what I wore. It was as much a part of my morning routine as washing my face, and I took immense satisfaction in seeing my Stylebook calendar filled out with my daily looks. By meticulously keeping the app up to date, I could see the cost-per-wear of each item, which I then used to justify splurging on some nice pieces, like upgrading my H&M faux-leather jacket to a high-end one and investing in an Outdoor Voices sweat set to upgrade my lounge game.

Conversely, by being able to see how long it had been since wearing each item, the app helped me identify the clothes that should be donated or resold. Of course, I still kept some pieces for sentimental reasons, like the dress I was wearing when I met my husband, but Stylebook encouraged me to be better at letting go of the clothes I’d grown out of, literally and figuratively.

A snapshot of what my Stylebook closet looks like.
Image: Apple Store via Polygon

It was a glorious time. And then the pandemic hit. All the clothes I spent so long logging into Stylebook sat unused in my dresser. In April 2020, I packed every pair of jeans I owned into a suitcase and shoved it into the dark recesses of my closet, not to be opened again until November 2021. After five years of being a key part of my daily routine, Stylebook suddenly felt irrelevant, like it belonged to another person in another life.

I briefly tried to revive my daily outfit log in January 2021. I’d just been laid off and was desperate to reclaim any sense of structure in my life. The practice lasted a few months, even though I found myself just logging a rotation of the same sweatshirts, sweatpants, and sweaters every morning. After a while, I accepted that the daily pressure to keep it updated was more exhausting than rewarding, and gave up on the log again. But I could never bring myself to delete Stylebook, or even remove the app from the prime spot on my home screen’s top row, nestled between Messages and WhatsApp.

My most-worn item this month was a $16 pair of gray Old Navy sweatpants (culmulative cost per wear: $0.66).
Image: Apple Store via Polygon

I no longer document what I wear — therefore negating the entire purpose of getting the app — but I still maintain my digital wardrobe with as much attention and care as I did before, uploading each new purchase and deleting items I’ve donated. At a time when I’m trying to be more purposeful about where I spend my time and energy, I’m not sure why I continue to keep my Stylebook app up to date. Maybe it’s in the hopes that I’ll eventually become a person for whom it’s more useful again — one who socializes, travels, and gets to dress up more. Maybe it’s an affectionate memorial to who I used to be. Or maybe it’s simply because I just like organizing things, even if creating the organizational system is the purpose rather than a means to a more actionable end.

No matter the reason, I don’t think I’ve ever had a healthier relationship with Stylebook. It’s been incredibly freeing to accept that it’s OK to only take advantage of a small percentage of an app’s purpose or potential. I no longer feel guilty over forgetting to input that day’s outfit, and it’s nice knowing that if I ever do want to scroll through clothing options or make another packing list, the app is patiently waiting for me at the top of my screen.

Now that the weather’s nice and I’m starting to get out and travel more, maybe I will even begin using Stylebook more regularly again. But to be perfectly candid, I hope I don’t.

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