You’d think with all the traveling I do as founder of Wine Lovers Travel that I’d be able to pack for my trips in my sleep.
You’d be wrong. Yes, I do have certain steps I’ve adopted to make packing less stress-inducing. I keep my toiletry bag ready to go at all times. That includes my lotions, potions and make-up, all dupes of what I use at home. When I return from a trip, I immediately restock what I’ve used and order replacements from Amazon as needed. That way, I don’t have to scramble to remember what to bring every time I pull out a suitcase.
I’ve also become a disciple of packing cubes. They really do save space and make it much easier to unpack (or not) at my destination because each type of clothing is in its own cube.
But that leaves the bigger question. What do I put in those cubes? I’ve read hundreds, if not thousands, of tricks and tips. Have a simple color scheme, like black, white, cream and navy. Spice it up with a scarf. The problem is that’s not my look. My tastes run to colorful, one-of-a-kind pieces spiced up with some bling. Essentially, create a capsule wardrobe of basic clothing and accessorize it with a scarf to add a touch of brightness.
So, do I pack 1 or 2 unique outfits for every day of the trip and end up with more luggage than I can check for free?
Suddenly, the solution came to me. I’m using AI for so many other tasks, why not use it for packing? I’ll describe what I want to take and have it come up with a good wardrobe that can be mixed and matched so that even with my eclectic clothing, I don’t have to fill up multiple suitcases.
For my recent trip to Europe, I told my friend ChatGPT that I’ll be gone 17 days, including an 8 day small ship cruise from Nice to Barcelona, a few days exploring the Loire Valley in France by car and a quick wrap-up in Paris. Also told Chat the dates I was traveling.
Next, I described what I was thinking of taking, with a little detail about style and color (a yellow tank, a houndstooth cream blazer with clear sequins, for that bling I love). I suppose I could have taken photos of everything and attached them, but that was more effort than I wanted to make. I hit send and within a nanosecond, Chat is spitting out a capsule wardrobe for me.
Not bad ideas. The first go-round wasn’t quite right. For example, my functional trench is only to keep me dry if it rains, but it is not a fashion statement. It’s fine to bring it, but don’t count on it to dress up an outfit.
After a very few tweaks, I had a great packing list. Most of the items were pieces I already own, and it also gave me a specific shopping list for a few gaps I didn’t have. That meant when I made my last-minute trip to the mall, I didn’t panic. I had specific items I needed, which made the shopping much easier, without the anxiety I usually feel when I know I need things, but have no idea what.

Not only did Chat provide a shopping list, it also offered me a packing checklist to make sure I remembered everything and a calendar of how to mix and match by day and location so that I was always the fashionista I strive for without having to think about it.

Now the next time I travel, which is always just around the corner, I’ll ask ChatGPT to help me. It relieved the tension and allowed me to begin my trip confident that, no matter what happens on the trip, I’ll look great!
