dressing in the age of the algorithm

meditations on 5 years of getting ready on tiktok

john singer sargent, nonchaloir (repose)

The weekend leading up to the tiktok ban, I spent the final hours death scrolling my 5ish years of posting on the app. Beyond the mix of emotions, I was reminded how much my personal style and consumption habits have shifted in a relatively short amount of time.

This week’s essay is a reflection of how my personal style has changed in the past 5 years (all of which is conveniently and permanently documented on the internet!!!) It was inspired by this comment from ryan (note: if there’s anything you’d like to see in a future post, please drop me comment!)

Looking back, it’s hard not to get annoyed with myself at outfits I put together or trendy purchases I made, but I’m reminded of this quote from menswear guy:

When it comes to buying things, I’m fine with buying on impulse. Sometimes, I’ll give it a day or two to see if my initial enthusiasm holds, but I’m very comfortable buying things on a whim. If the purchase works out, that’s fantastic; if it doesn’t, don’t let it bother you. There’s a Chinese phrase for when you lose money on something that translates to “paying school fees.” I’ve paid a lot of school fees, and I don’t consider any of it wasted money. Even through the mistakes, I’ve learned a lot.

Hopefully you can take away some of the lessons I learned (without spending nearly as much money):

---

2021

marked a time where I started to pay closer attention to what I was wearing, and posting about it online. The challenge was that I was still working with the closet I had in college/post-grad so the bulk of my wardrobe consisted of aritzia and miscellaneous thrift finds.

I often think that your wardrobe is a lagging indicator of your current fashion taste. The outfits I’m putting together today are mostly a result of the shopping I did throughout the last 12 months. Naturally, a lot of 2021 was spent aimlessly flipping through my closet and frantic trips to the williamsburg buffalo exchange.

#1 - Tread carefully with inspiration: The biggest ‘mistake’ I made is that in a period where I was trying to figure out how to revamp my wardrobe, my tastes became an echo chamber of what I saw online. The outfits I put together were all over the place, and I was susceptible to whatever was trending at the moment (read: fuzzy bucket hat). While I believe in experimentation, none of the outfits I recreated ever felt quite right . Now, I try to stick to the silhouettes/styles that look good on me and swapping out one or two things.

2022

was notable because it marked my first purchase on TheRealReal and a foray into designer vintage. I shopped a lot — mostly secondhand (eBay, TRR, vintage stores in brooklyn) and started acquiring versions of the basics I still wear today. I actually don’t mind many of the outfits here: you can see the “messy minimalism” start to emerge, although this also marked a departure from wearing any sort of color.

#2 - Try not to hyperfixate: I find that shopping designer is a much more emotional experience — I was very susceptible to hyperfixating on an item because I thought it would unlock a guaranteed **leveling up** of my closet. I spent most of 2022 hyperfixating on a pair of proenza schouler loafers that I eventually caved, purchased and spent a year stomping around in. But no matter how many times I thought one specific piece would “complete” my wardrobe, it never seemed to be the case.

2023

is where I gravitated towards more utilitarian minimalism — I still fell victim to some trendier items (the infamous Baggu collab), but mostly I had my basic looks mostly locked down.

#3 - Try before you buy: One of the things that really helped my shopping was that I started to organize my Pinterest by items that I wanted to buy vs just looking at blanket “outfit inspo”. This helped me figure out if there were enough ways to style a piece (with things already in my wardrobe) or if an item was a slippery slope into more purchases. Oftentimes my worst outfits are when I’m trying to emulate someone’s vibe vs an aspect of their outfit. A good litmus test for this is: do I actually like this outfit or do I just think this person is cool/ hot???

2024

I would say that I didn’t feel settled into my style until around 9-12 months ago. It felt like the previous three years, I was constantly racing to shop in order to put together outfits that caught up to my tastes. I’m rounding out a “no shop” january and I feel more confident in my personal style as I don’t feel a constant, insatiable need to shop (although I do still scroll TRR more often than I should).

#4: Invest in a steamer… seriously Utilitarianism is one of the things I prioritize in my wardrobe, but there inevitably will be items that need a good hem, steam or fix. I started to actually steam my clothes this year and spent ungodly sums of money on a good tailor and cobbler. Honestly getting clothes maintained can be such a chore, but it’s way more satisfying in the end to make something you already own fit perfectly than to buy something new that fits just okay. I think the meta learning here was to be way more critical in the clothes I buy and pay closer attention to how things fit rather than articles that I like on the rack.

Looking forward

Last month I wrote about engaging in fashion in deeper ways than just buying clothes — one nuance to this is that certain mediums will scratch that itch more than others. While I love making videos, I find that doing it too often leads me to be anxious about constantly coming up with new outfits. I’ve said before that 2025, I want to invest more into substack and reflecting, analyzing and researching fashion rather than just feeding the machine.

#5: To end, some ways to engage in fashion more creatively:

• listen to fashion podcasts

  • Fashion Neurosis: one of my favorite new fashion podcasts, i started with this one with Rick Owens

  • Articles of interest really peaked my interest in fashion history. A good bite sized listen is with the Tibi founder on How To Dress

• follow fashion writers on substack!!

  • anna’s post re-wired my brain into how to shop better and determining what is realistic vs aspirational in my wardrobe

  • emily north just published this brilliant essay that i think everyone should go read and then re-read every few months on how to make style more personal

• read fashion history books

  • I read Gods and Kings last year which was a deeply researched account into the rise of McQueen and Galliano — it’s dense but highly recommend if you want an inside look into some of the most influential voices in couture in the past few decades

• watch fashion adjacent films

  • I’m famously not a cinema girl, but that’s something I want to change so would love any recommendations here! some i’ve gotten so far: dior & me, the september issue, and according to my tiktok algorithm, the entirety of the devil wears prada in 30 second increments.