Why Style Feels Different As Life Changes

Originally published on Substack March 31, 2026

I can dress better at 66 than I ever could before and now I understand why.

I’ve had so many style periods in my life.

From the time I was a baby until the age of 11, it was my hand-me-down stage. I didn’t get a new dress of my own until I was 10. All my clothes came from a set of older cousins. And they were way cooler than me, so mostly it was okay.

Then my mom taught me how to sew when I was nine. By fifth grade I wore the same “uniform” every day: either an olive green wide wale corduroy skirt or an orange plaid skirt, a long puffed-sleeve white blouse, a button-down sweater vest, white knee highs, and white low-top Chuck Taylors.

In seventh grade, my mom helped me make the perfect black and white checked bell bottoms with violets in the print. I thought I was groovy, man. In eighth grade home-ec, I made a dress with a matching smock top, very on point for the time, right down to the buttons covered in the same fabric as the dress.

My first jeans came from my skinny mini uncle’s closet. Levis, of course. I stole them in eighth grade and wore them, with patches on the patches, all through college.

Later, in high school, I moved on to a closet full of turtlenecks, bell bottom jeans, and corduroy pants, all bought with babysitting money. My pride and joy were my Swedish blue clogs, which all my friends had too.

Then came marriage shortly after college, and motherhood.

That’s when I really stopped paying attention to what I put on my body. I had three pregnancies in under four years, and my body was changing so fast and never quite getting back to what I thought of as “normal” that clothing simply wasn’t a priority.

I always had a good eye, so I wasn’t embarrassing in public, but I wasn’t dressing my best either. Styles, fit, and color were all over the place. I even intuitively knew it wasn’t right, but I had too much on my plate to do anything about it.

Then came the years when my children were teenagers. We were a theatre family, and I was a children’s theatre director. I spent my days in black sweatpants and show shirts.

Honestly, I loved that period of time. Even if I wasn’t the most stylish, those show shirts still hold so many memories.

Looking back, I can see that each of these phases wasn’t just about clothes. It was about what my life could hold at the time.

But now, I’m in a completely different stage of life.

I’m at retirement age, with no intention of retiring. And I’ve come back to style, something I always loved but never really allowed myself to fully engage with.

It took me years of study to become a Style Coach™ and color analyst, but more importantly, it took time to understand how I wanted to present myself to the world.

I had to learn how to dress my changing body and my changing hair. I stopped coloring it. And I discovered something surprising.

I can look better at 66 than I ever did in the previous 60 years.

That’s a hard thing to face.

Not because I don’t love how I look now. I do. I love the cohesive wardrobe I’ve built. I love how I show up.

But because I can see now that I could have looked better all along. Not perfect. Not styled to the nines. Just more like myself.

I never gave myself permission to pay attention to what I needed or how I wanted to show up.

And I don’t think I’m the only one.

For so many women, it’s not that we don’t have style. It’s that our lives, our responsibilities, and our changing bodies shift our attention elsewhere.

And by the time we look up again, what used to work no longer fits who we are now.

Maybe the next step is simply paying attention again.

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