Substack = the ChatGPT for getting dressed
Inside Substack fashion + beauty chats: the closest thing we have to a human-powered fashion search engine.
I’m obsessed with this topic. I’ve written about personalized search for dressing before—most recently about Daydream’s imminent launch. (Still curious how a fashion search engine fueled by pre-determined partnerships will manifest). I’ve been watching closely to see who would try to fill this obvious gap in e-commerce.
Despite how quickly our dollars have moved online—supercharged over the past five years—no one has effectively solved for this pain point.
Most new fashion tech has focused on B2B solutions, resale, and circularity, leaving consumer-facing search largely untouched. Maybe because of the breadth of the challenge, or, no one feels like going up against Google and probably Apple too.
But here’s the real David & Goliath story of fashion search: Substack.
As far as I understand it, this Substack search story traces back to a few key fashion influencers who joined the platform a few years ago—many bringing large audiences with them. Leandra Medine and ex-Man Repeller writers come to mind. Their newsletters gained traction, and at some point, so did their Substack chats. And that’s where the real magic lives.
I originally dove into Substack because I started a newsletter and am building a fashion tech product for consumers and need to understand what people want to buy and how they find it. I’m in ~13 different fashion or beauty adjacent chats. Some require a paid subscription to participate, but lurking is allowed. Most let you join in whether or not you pay for the newsletter itself.
Picture your friend group chat tailored to fashion and beauty subjects—every niche interest covered. There is enough anonymity that invites you to ask your burning consumption questions. I recently asked for, “the best glossy berry lip gloss suggestions.” I got 12 detailed responses within 20 minutes with background context, links, selfies and up voting from chat lurkers.
These chats are further evidence that the sheer number of choices in brands and products, have led to consumer overload, the demand for trusted input has skyrocketed. People are hungry for personalized recommendations.
The bulk of my IRL community isn’t in the Substack chats. Many of my friends probably never will be—it’s not for everyone. But when I bring up how into these convos I am, the most common response I get is: "It’s like Reddit?"
Eh, kind of. But more immediate responses and elevated for sure.
Crowdsourced Fashion > AI’s Style Advice (as is today)
As Fashion Substacker, describes her newsletter, “presenting product discovery in a less editorialized way.” And that’s the feeling. Each chat has its own distinct vibe, and I know exactly what kind of perspective I’m going to get from each one.
- As an older millennial, when I need some Gen Z insight, I’ll check in here—whether it’s for vintage shopping tips or niche brand discovery. The crowd is resourceful—if you’re hunting for the perfect vintage Helmut Lang jacket someone here will probably have an idea. - This chat is a fashion girl’s roundtable—a Zillennial playground where cheap thrills aren’t mentioned. It’s all luxury here. It feels like everyone in this chat has a strong sense of personal style. Here, you’ll hear about what’s peaking, what’s over, and what’s pre-mainstream. And yes, someone’s friend’s handmade balaclavas brand will get a mention. Chic. - The slow fashion devotees! Thoughtful, well-researched discussions on everything from shopping guides for Charleston to fiction book reviews. There are loads of styling advice threads, dissections of product launches, resale opportunities, and analysis of social media campaigns.Each of these chats function differently, but they all offer the same thing: a direct line to thoughtful, highly specific fashion convos & an answer to many of your phone-a-friend styling moments.
Why These Chats Work Better Than Anything Else (right now)
Crowdsourcing looks & personal styling
You post a pic of an item, and this crowd will give you their take on how to style it. Need an outfit for a work trip to Davos? First time at the opera? Packing for Paris? These are daily questions, and the responses are hyper-specific.
People don’t just ask questions—they provide detailed context. Price point? Open to custom? And at the end of the thread, a thank-you message from the original poster. And maybe even a follow up of how the group’s advice helped.
Product sourcing + discount codes
From hard-to-find RealReal gems to the best slip-free Pilates leggings to slouchy jeans that work for short girls, these chats are constantly sourcing.
Brand validation
Not sure if a brand is actually good? Ask here. From how to break in Wejuns to the best work tote, at various price points. Someone recently asked if, “Still Here denim is actually great denim or just a trend?” People seem to think its great.
"Should I keep, buy, or sell?"
Resale is happening here too—P2P sales in real time. P2P resale in these chats is an amazing opportunity to convert people who have been wary of secondhand shopping, especially those in certain income brackets.
Yes, it’s up to you to parse through this data, additional research is needed. These are mostly strangers in these chats, just to confirm. Some of the authors of the newsletter will chime in, which I think is part of the Substack appeal. This appears to be the case for some of Emily Sundberg’s success with
. Her personal interactions with her readers.Other chats to check out,
- , The Love List
I wish Styled by Code’s group chat would pop off! Maybe in a month or so, when we release our MVP, fun convos will emerge.
At the end of the day, the Substack chat is the only working fashion ‘search engine’ —opinions, context, and a shared understanding of style and taste.
How can brands get in on the action? That’s a topic for another time.
jumped in, in the cheekiest way! A hard act to follow.Leaving you with a quote I heard from Trinny Woodall on Bella Freud’s podcast:
"The right outfit can change your entire outlook on life."
This was such a fab article. Eating it up girl—gospel!!
love this