I Let ChatGPT Pick My Makeup at 68 — Now I’m Wearing It for 30 Days
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At 68 years old, I did something I never thought I’d do.
I let artificial intelligence tell me how to do my makeup.
Yep.
ChatGPT looked at my coloring, analyzed my undertone, suggested colors that should work better for me, and basically told me, Gigi, we need to talk about some of these choices you’ve been making.
Okay, maybe it didn’t say it exactly like that.
But that’s what I heard.
And here’s the kicker:
I’m actually going to listen.
For the next 30 days, I’m wearing the makeup and colors ChatGPT recommended to see whether an AI really does know something I don’t.
Because apparently retirement wasn’t enough of an adventure.
Now I’m taking beauty advice from a computer.
Welcome to 68, baby.
This Isn’t About Looking Younger
Before we go any further, I want to make something very clear.
I’m not doing this because I’m trying to look 48.
I’m 68.
I’ve earned this face.
The lines, the changes, the things that aren’t sitting exactly where they used to sit — they’re all part of living.
What I’m curious about is something different:
Am I still choosing makeup based on what worked for me years ago instead of what actually works for me now?
That’s a much more interesting question.
Because reinvention after 60 doesn’t always have to mean changing your entire life.
Sometimes it’s changing your lipstick.
How This Whole Thing Started
This experiment actually started with a conversation by daughter, Stac about color.
I wanted to know my undertone and which colors would complement me best. So I gave ChatGPT photos and asked it to analyze my coloring.
From there, we started talking about makeup.
Foundation.
Blush.
Lip colors.
Eye colors.
The whole thing.
And some of the recommendations weren’t necessarily the colors I would have automatically reached for myself.
That’s when my curiosity kicked in.
Because if you’ve been around Gigi’s Unfiltered for a while, you already know how I am.
Tell me something might work and eventually I’m going to say:
Fine. Let’s find out.
So instead of buying the makeup, trying it once and deciding whether I liked it, I decided to make this a real experiment.
Thirty days.
🎥 Watch the Experiment: I Let ChatGPT Pick My Makeup at 68
Watch me apply the ChatGPT-recommended makeup for the first time, see my real reaction, and hear why I’m committing to wearing these recommendations for the next 30 days.
Day One: No Hiding
For the first day of the experiment, I started without makeup so we would have a real before.
No pretending.
No carefully chosen “before” designed to make the “after” look miraculous.
Just me.
Then I applied the products and colors ChatGPT recommended while recording my genuine reaction.
And that’s important to me.
I didn’t want to already know what everything looked like and then come back later pretending to be surprised for the camera.
You get the real reaction.
Good, bad or:
ChatGPT, what the hell were you thinking?
The Makeup ChatGPT Chose for Me
For this experiment, I’m focusing on the shades and products recommended for my coloring and undertone rather than chasing whatever happens to be trending.
I’ll update these sections with the exact products I’m using so you can find them if you’re curious about trying something similar.
But remember: what works with my coloring isn’t automatically going to work with yours.
That’s part of what makes this experiment interesting.
And Of Course There Was an OOTD
You didn’t really think I was going to put on a whole new face and then ignore the outfit, did you?
For my Day One look, I paired the new makeup with one of my Zeagoo tops.
And here’s something I always want to be transparent about: Zeagoo was already in my closet before there was ever an affiliate relationship involved.
I’d bought and worn their tops because they fit the kind of wardrobe I’m building now — comfortable, colorful and easy to wear without feeling like I’m disappearing inside my clothes.
So when the opportunity came along to work with them through Awin, it made sense.
I was already a customer.
And that fits this experiment perfectly.
Because my whole Funeral to Boho journey has been about letting color, personality and a little bit of that old hippie girl back out.
The makeup is becoming another piece of that.
The 30-Day Rule
Here’s where I’m making myself behave.
I’m not judging this experiment based entirely on Day One.
We’ve all tried something new, looked in the mirror and immediately thought:
NOPE.
Sometimes it’s actually wrong.
But sometimes it’s simply unfamiliar.
So I’m giving these recommendations approximately 30 days.
I’m going to wear the colors.
Live my normal life.
Film videos.
Take photos.
Get dressed.
Look at myself in different lighting.
And most importantly, give myself enough time to determine whether I dislike something because it doesn’t work — or because it isn’t what I’m used to seeing.
That’s a big difference.
Then Claude Gets a Turn
Oh yes.
We’re not finished.
After I’ve spent about a month testing ChatGPT’s recommendations, I’m planning to do the same experiment with Claude.
New analysis.
New recommendations.
Another real-world test.
And eventually we’re going to have ourselves a little showdown:
ChatGPT vs. Claude: Who Actually Knows My Face Better?
I have absolutely no idea who’s going to win.
It might be ChatGPT.
It might be Claude.
It might be 68-year-old Gigi saying:
Thank you both very much. I’ll take it from here.
And honestly, that may be the best possible ending.
Maybe We Should Question Our Own Rules Sometimes
This experiment is supposed to be fun.
But there’s something underneath it that feels very connected to everything I’ve been talking about lately.
How many things do we keep doing simply because that’s how we’ve always done them?
The same makeup.
The same hair.
The same clothes.
The same colors.
The same ideas about what women our age are “supposed” to look like.
I’m not saying we need to change everything.
I’m saying maybe it’s worth getting curious.
Try the lipstick.
Wear the colorful top.
Ask the ridiculous question.
Let the AI pick your makeup.
You might hate it.
You might love it.
But at least you’ll know.
At 68, I’m discovering that curiosity might be one of the best anti-aging products I’ve got.
And baby, that one doesn’t cost a dime.
Come Back in 30 Days
This is officially Day One.
I’ll be documenting what happens over the next month, and then we’ll come back and compare where we started with where we ended.
After that, Claude gets the same opportunity.
And eventually we’ll bring the whole experiment together:
ChatGPT vs. Claude — The Final Results
Same woman.
Same face.
A whole lot of curiosity.
Let’s see what happens.
And ChatGPT?
No pressure, baby.
But Claude is waiting in the wings.
