TLDR: ThredUp rebuilt its platform around AI. Visual search, style chat, and smarter discovery make secondhand shopping feel as easy as fast fashion, and the stock is up about 641% y/y as of recording the video above. The company is growing fast, but if its buyer-facing AI tools don’t meet basic standards, they will break trust and risk losing the platform’s super users.

I have never claimed to be a minimalist. I am someone who enjoys window shopping at curated vintage stores and Brooklyn boutiques far out of my price range, with the hope that the next pair of jeans I get will finally be “the one.” I now have over 30 pairs of jeans, and while none of them are “the one,” some of them are “these will work just fine.”

Over the past year, I have started to venture more and more into the secondhand online shopping world, a place I previously didn’t look much into in fear of getting a product that still smelled like someone’s dog or didn’t fit and was unreturnable. Poshmark has burned me too many times. The RealReal has been a flop. eBay scares me.

Then I found ThredUp, a secondhand platform that lets users buy clothing or have their clothing sold by the company, similar to a consignment store. In this case, all clothes that do not sell are kept and donated. I don’t remember the first time I came across it, but I do know I get a lot of their ads on Instagram and they sponsor some lifestyle YouTube videos.

ThredUp offers high-and-low items at prices that make my eyeballs fall out of my head. You have to hunt a little, but that’s why the term “the thrill of the hunt” exists.

It has been my site for getting $12 100% cashmere sweaters, $60 suede Gucci flats, and more vintage athletic apparel than I care to admit, but what can I say. It was way better back then, and I think I look like Jennifer Aniston when I wear it. Almost all of my items have been returnable. My Prada sandals broke after two wears. They refunded me - no questions asked.

The high I felt when I first found ThredUp was akin to when I first used Pinterest. I got in the flow state.

Then things changed.

Well… things changed enough to bug me a little, but not to totally stop using it.

I was scrolling their app recently while out, pretending I was looking busy on my phone while waiting for my friend, Caroline Fish was in the bathroom because what was I supposed to do, sit there and enjoy a calm moment like a crazy person? It became a very not-calm moment for me when I realized that some of the products I was looking at looked different across the photos in the listing for a Madewell top. The model was simply just wearing a different top and it gave me no guidance on what it looked like. To make matters worse, I could tell it was AI and she looked awful in the top that looked like it was almost melting and warping around her. They could have at least had some decency and given this poor AI character a chance. Now it was just a poorly done AI depiction of what the top would look like on a real human, and it was ugly.

If I keep having issues with ThredUp, could become just another Poshmark.

A feather in the wind.

I miss it already.

That hasn’t happened yet though. They added some tech to the platform that basically makes it as easy as shopping on a fast-fashion site.

ThredUp went all-in on AI

ThredUp has rebuilt itself around AI this year. The platform rolled out Style Chat (natural-language styling), visual search (upload a photo to find similar items), automated tagging, 360-degree product photography, and AI-generated model images (the bane of my existence).

Half of all new customer searches now use visual AI components. I used that feature too - it was great. It was similar to using Google Image Search, but directly on the app. Shoppers who use image search are 85% more likely to buy. The company’s adding 60K new items daily, making AI-powered discovery basically essential at this scale.

Daily Edit serves up 100 AI-curated items at login, and although it wasn’t the first place I used to go when opening the app, the selection had some hits. Weekly Trend Report maps AI-generated trend analysis to inventory. One reason things seem to have fell into place is ThredUp hired Teleport cofounder Danielle Vermeer meer to build a more social, TikTok-native interface. She obviously knows her shit. I got hooked.

The business is responding well. After years stuck between $1 and $4 per share, ThredUp’s stock hit $10, with double-digit revenue growth, more new buyers, and higher total orders.

Even the inside of their warehouses are impressive, I hope the people that work there are treated well, because man, photos of this place make Amazon look like chump change. Workers inspect every item and QR codes track each garment through a 100K-square-foot hanger system. Automated photo rigs capture 360-degree imagery and a dedicated team authenticates luxury brands that come through.

The backlash

With all of the efficiencies and customizations AI is offering, and good hires ThredUp went through to get it to where it is today, Reddit isn’t celebrating.

Over on the Subreddit r/ThredUp, they are freaking out and saying “If it has an AI image, I’m not buying it.”

Reddit users in r/ThredUp describe patterns that appear “warped,” “melting,” or “stretched,” along with colors that look oversaturated or altered. Models often seem to be the wrong size for the garment, making the fit look misleading.

Some users are even saying that the AI could be working with bad inputs from rushed warehouse staff feeding incorrect data, which then generates distorted model images.

Multiple longtime shoppers say they’ve stopped using the platform entirely because they can’t trust the AI-generated photos.

Losing a few shoppers probably won’t hurt them, and I actually don’t think crappy AI-models would keep most people from using the app. Things will start getting sticky if AI quality control does not expand to other areas. With so much change happening, there needs to be a way to sustain excellence.

ThredUp is a sustainability-focused brand. The whole pitch is “buy secondhand, reduce waste, make fashion circular.” If the AI imagery misrepresents the actual clothing, even unintentionally, it breaks the trust that makes secondhand shopping work in the first place.

(Important caveat: these are Reddit user complaints, not confirmed platform issues)

Tech in the processes

Thrifting online is inherently risky. You can’t touch the fabric. You can’t try it on. You’re basically betting on if measurements taken in a warehouse at lightning speed, some product photos, and now an AI-model, translate into something that will live up to your expectation. That bet only works if all attributes of the listing are honest.

The AI-model part of this all adds a layer of artificiality on top of that very tangible process, and shoppers can totally tell.

The company is betting that AI can make secondhand fashion accessible enough to compete with fast fashion’s convenience. Convenience is the biggest barrier to secondhand adoption, so if ThredUp can get new buyers (especially the 25–35 demo they’re targeting) to choose thrifting over ordering from Zara, that’s a win.

The Reddit backlash is a big warning sign though. People came to ThredUp because they wanted actual clothes, actual sustainability, actual secondhand shopping. If the AI tools make the experience feel less authentic, they risk alienating the core audience that made the platform work in the first place.

If you’ve shopped ThredUp recently (with or without the AI images), I’m curious, did the photos match what showed up?

Check out their company Substack at Thredit.

Tech News

• Speaking of secondhand, Facebook Marketplace got a glow up. Meta updated Marketplace with features like collections, collab buying (great for you and a roommate or partner), comments (these will get so messy lol) and AI integrations.(Meta)

• Jack Dorsey is funding diVine, a reboot of Vine that brings back more than 100K old videos and lets people post new ones. The app blocks suspected AI generated videos and verifies that uploads are recorded by real people. It is built on the decentralized Nostr protocol and arrives before Elon Musk’s promised Vine revival. (TechCrunch)

• OpenAI dropped GPT 5.1 in the API, including “no reasoning” mode and up to 24 hour retention to generate faster responses. I am most excited for Sam Altman saying that ChatGPT will now actually follow requests for no em dashes. Huge. (OpenAI)

  

• Cursor raised a $2.3B Series D led by Accel and Coatue at a $29.3B valuation. This comes after the AI coding startup’s $900M Series C raise in June, which valued the company at $9.9B. We need some more details here. (Cursor)

• Fei Fei Li’s company World Labs just launched Marble, its first commercial world model that turns text, images, or videos into editable 3D environments. Marble creates persistent, downloadable worlds and comes with editing tools that let you shape the scene before the AI fills in the details. This is about to make VR and VFX so much cooler. (World Labs)

• Gartner surveyed 700 CIOs and says that by 2030, all IT work will involve AI, with bots handling a quarter of it. That shift comes with new buzzwords: an “AI accuracy survival kit” for tracking model errors, “pipeline choke” when AI replaces beginner tasks and no one learns the basics, and “experience compression” when juniors perform like seniors with AI tools. They also warn about skill atrophy as people outsource simple tasks, and a “capacity paradox,” where faster AI-powered teams risk looking unnecessary if leaders don’t put that extra bandwidth to good use. (The Register)
  

Thanks for reading! Let me know if you like this format, or if the section up top was too long. I am always switching it up around here. - Rachel Braun

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