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

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.

Stylebook was a tool that helped me to see what items I had and how frequently I used them. 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 — okay, months —My Stylebook closet is now ready to go. The process involved taking pictures of 200 items of clothing and footwear, then manually erasing background to create facts and descriptors. This helped me to track my buying habits and identify trends in my wardrobe. 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.

Polygon image of the Apple Store

I then created folders that organized the items by type. Tags were also used to help you find what clothes to wear for a particular event like a wedding or job interview. It saved me time and helped me save valuable time by creating packing lists and putting together outfits for future trips. 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. This was a regular part of my morning routine, as well as washing my skin. It gave me immense pleasure to see my Stylebook calendar with every day’s 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.

The app also allowed me to track how many times I had worn each piece, which helped me determine whether it was time for the clothing to be donated or sold. 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.

Polygon image of the Apple Store

This was an amazing time. But then, the pandemic. My dresser remained empty of all the clothes I spent hours logging into Stylebook. All my jeans were packed in a suitcase. I then put them into a bag and put it away. It was not opened until November 2021. Stylebook, after five years, felt like an irrelevant part of my daily life.

In January 2021, I tried briefly to revive my daily outfit journal. I’d just been laid off and was desperate to reclaim any sense of structure in my life. The routine lasted for several months even though it was a repetitive rotation of sweatshirts, sweaters and sweatpants each morning. It was exhausting and rewarding to maintain the log, but I eventually gave up. 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.

Polygon image of the Apple Store

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 okay 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 You might also want to use Stylebook regularly. But to be perfectly candid, I hope I don’t.