Stop packing outfit soup

June 4, 2026

By Kim Komando

Before I went to California last weekend to escape the Arizona heat, I asked ChatGPT for help. I’m the person who packs three shirts for the same dinner, then wears the same black T-shirt four days in a row.

I was pulling things out of my closet, doing that deeply American ritual where you know the weather, sort of. You know the activities, sort of. You know your own clothes, sort of.

Then, I thought of a new use for ChatGPT’s camera feature. I laid my clothes on the bed, took photos and said, “Here’s the pile. Turn this into outfits before I overpack, underpack or spiral.” 

Not because AI is Anna Wintour. Because AI’s patient enough to do the annoying pattern matching my brain refuses to do. 

🧳 Do this before your trip

Open ChatGPT, Claude, Gemini or Grok and paste this:

You’re my pro travel outfit strategist and packing editor. I’m uploading photos of the clothes, shoes, bags and accessories I’m considering bringing. Your job is to turn them into a practical outfit plan, so I don’t overpack, underpack or wear the same thing every day.

● Trip details (destination, dates, length) 
● Weather: Look up the forecast and factor it in
● Laundry access: [yes/no/unknown]
● Luggage limit: [carry-on only/checked bag]
● Activities: [beach, dinners, hiking, work meetings, sightseeing, Pilates, running, etc.]
● Dress codes: [restaurants, events, work, workout, etc.]

After I upload the photos, create an image plan of “10 outfit ideas” using only the items shown unless something important is clearly missing. For each outfit, include the pieces, best occasion and a short caption. Then tell me what to cut, what’s missing and which pieces mix the best. Ask me clarifying questions only if you need them before making the list.

Done. Barry will pack one bag in three minutes. It’ll have swim trunks and a sport coat and nothing that goes with either. The AI has its work cut out.

📩 Send this to the person who packs seven tops, three pairs of shoes and still wears the airport hoodie all week.