I never imagined, at 58 years old, that I’d find myself watching video tutorials on how to apply eyeliner.
I’d always had a bohemian, makeup-free vibe that had worked just fine when I was younger. I used to laugh at the idea of coloring gray hair and swore I’d never ever consider plastic surgery.
Of course, those are easy positions to hold when you’re in your teens and 20s. However, when you’re staring 60 in the (somewhat wrinkly) face, it’s a different story.
Then one day, my company changed its remote work policy. Faced with the reality of going back to working with others in person, I realized I was in trouble.
I knew I had to do something about my appearance … fast.
For me, returning to the office meant I had to put more work into how I looked
Though I looked forward to seeing colleagues and collaborating IRL, I was worried.
The thing is, everyone on my team is younger than me. Some are much younger — in their 20s. Less than half my age. In our video calls, they all seem to have amazing makeup, hairstyle, and fashion skills that I don’t.
My appearance had only gotten frumpier while working from home every day. In fact, I kind of let myself go.
At best, I wore a white blouse and black blazer paired with plaid pajama bottoms and fuzzy unicorn slippers. (Professional on top, naptime on the bottom.)
Soft-focus filters on video calls helped me feel mostly fine with my appearance. It was a comfy lifestyle.
I didn’t want to go back to wearing real pants … or shoes with heels. However, I didn’t have a choice. My team was about to see the real, unadulterated, unblurred, undyed me.
It was time to get serious about putting in some effort and making myself look better — and yes, trying to look younger.
First, I used a ChatGPT color analysis to help me make more flattering choices
I knew I wasn’t going to be able to do some kind of miraculous makeover in a few weeks, and I didn’t want to look unrecognizable, either.
In desperation, I turned to generative AI. I asked ChatGPT for a color analysis so I could understand which shades of makeup and clothing would look best on me.
I uploaded a headshot taken in natural light, without makeup. Then I used a photo-editing tool to pinpoint the hexadecimal colors in my face, hair, eyes, and lips.
Using those colors, I asked ChatGPT to detect my undertones and contrast and tell me which “season” of shades would flatter me most.
Based on the analysis, I’m a “soft autumn.” I learned that my most flattering colors were shades like olive, sage, camel, rose, and terracotta.
I discovered that I should try to keep my wardrobe and accessories warm and subtle — never stark or icy. I’d been wearing black and white my whole life, and apparently, it’s not the best idea for my complexion.
Good to know! I sorted my wardrobe accordingly. Now, if I wear a black or white shirt, I soften it with a rust-colored scarf or a sage sweater.
I learned about applying makeup by watching tutorials, and finally dyed my hair
I then turned to YouTube, which is a fountain of knowledge for finding a fountain of youth.
After watching an overwhelming number of tutorials on how to put on makeup, I realized I’d been doing it wrong my whole life (when I did it at all).
For example, with eyeliner, I found out I should use go for a soft, smudgy look instead of a hard line or a winged shape if I want to best enhance my eyes.
I also got my eyebrows threaded (ouch!) and bought an eyelash curler (ugh).
At my next salon visit, I got warm gold highlights to blend the gray in my hair with the brown. My stylist also showed me how a diffuser could give my hair bounce and body.
I’d been fighting the natural wave of my hair all my life, but as I’ve gotten older, the waves have been winning. So I surrendered and was pleasantly surprised.
All in all, looking better helps me feel better, too
When I walked back into the corporate world, in person, I felt a lot more confident. I felt I looked less like a crazy cat lady and more like a cool aunt.
And when I told my team my real age, they all seemed gratifyingly shocked.
In the end, I made some incremental improvements that didn’t cost much and gave me a great return on my investment. What’s even more important is that these efforts feel sustainable.
I can spend a few minutes in the evening choosing an outfit for the next day. I’m willing to devote more time in the morning doing makeup and hair. And it’s certainly worth it to go to the salon for a cut and touch-up every few months.
I’m still not wearing heels, though. You have to draw the line somewhere.
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