How to Use AI to Style Yourself

I recently tried something a little different with how I shop—and it didn’t go the way I expected —in a good way.
You can read that here → StitchFix vs. AI

1. Build a Pinterest board

   Pull together outfits you actually love—not what you think you should like.
   The more consistent it is, the better this works.
   Take screenshots of your board.

2. Open ChatGPT

   Start a new chat.
   Upload your screenshots
   Drop the images directly into the chat.

3. Add your measurements

   Be specific.

   Include:
   Bust
   Waist
   Hips
   (Height optional)

4. Be clear about what you want

   1. Don’t be vague.

      Say things like:
      “Blouses that work under a blazer”
      “Structured but not stiff”
      “No clingy fabrics”
      “Nothing trendy or oversized”

5. Ask for specific items

   Say:“Find me specific tops I can buy that match this.”

6. Refine the results

   If something is off, say so:

   “Too casual”
   “Too boxy”
   “Not my style”

7. Order a small batch

   Start with 4–6 pieces.

8. Try them on and adjust

   Tell it what worked and what didn’t so it can improve the next round.