AI Startup #4: Fashion or Disaster

Richard Reis
3 min readApr 27, 2024


Link here

It’s been two months since I started my “25 AI Startups in 50 Weeks Challenge.”

So it’s time to unveil startup #4: Fashion or Disaster!

Sidenote: Launching on Product Hunt in 3 days. Please check it out 🙂

The story

“Can you build Cher’s closet app from Clueless?”

Paige Harriman threw me this curveball after our podcast interview.

Sidenote: I recommend giving the episode a listen if you’re an audio person and want to know more about the AI challenge! (Spotify link, Apple podcast link)

Now, if your last Clueless viewing involved dial-up internet and a high school sweetheart (like mine did), here’s a reminder:

Basically, the app judges your outfits.

The crazy thing is, Paige’s question couldn’t have been timelier. OpenAI had just launched GPT-4 Turbo with Vision, and I was actively looking for an image analysis project.

And then there was this tweet…

So, huge thanks to Paige for the idea and her help in building it!

The product

Introducing Fashion or Disaster!

Note: If this app reminds you of anything else, it’s purely coincidental… Also, I’m joking.

Upload a picture of your outfit and the AI will deliver its verdict: “FASHION” or “DISASTER,” along with a short (and sometimes hilariously honest) opinion.

Sometimes the AI is nice.
Other times… not so much.

Think of it as your own digital Miranda Priestly or Edna Mode.

It’s a fun little app 🙂 Plus, you get one free judgment when you create an account (after that, it’s $1 for 10 searches)


Now, I’ll admit, my personal style is more “black t-shirt and shorts” than “haute couture.”

So, I sent Fashion or Disaster to some friends who actually own clothes with buttons, and their reactions blew my mind…

I’m… speechless.

Turns out, there’s a genuine opportunity here!

I looked into the “AI Stylist” niche, and found growing apps like Style DNA, Aiuta, and Stylee.

It’s a brand new space (low competition, yay!) with real demand.

Working on this project was a joy. Give it a try and share your thoughts.

Now if you’ll excuse me, I must shift focus to AI Startup #5 (launching in two weeks because who needs sleep anyway?)

Catch you later! 🙂

Thanks for reading!

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Relevant Links

I Will Build 25 AI Startups in 50 Weeks” (what announced the challenge)

25 AI Startups List

  1. AI Document Translator: Translate documents cheaply, with superior AI quality. (post here)
  2. AI Hypnosis: Experience hypnosis tailored uniquely for you. (post here)
  3. AI Subreddit Finder: Find relevant subreddits instantly. Without endless browsing. (post here)
  4. Fashion or Disaster: Your personal AI stylist, inspired by Cher from Clueless’ app. (post here)
  5. Blog Memorizer: If Anki and blogs had a baby. (post here)
  6. AI Personalized Resumes: Tailor resume to job descriptions. (post here)



Richard Reis

"I write this not for the many, but for you; each of us is enough of an audience for the other." - Epicurus