Don’t Tell Me I Can’t Wear Ripped Jeans in My 60s

By Sheryl Kraft
February 26, 2024

Don’t Tell Me I Can’t is a series designed to celebrate all the ways you can forge your own path well into midlife and beyond.

A few years back while visiting my 90-year-old father at his assisted living facility, he looked at me and then pointed his finger toward my knees, or more specifically, to my jeans. My ripped jeans.

That look was familiar: a mix of curiosity and judgment. It brought me back to 50 years earlier, when, in defiance, I’d painted bold, red stripes on the front of my bedroom door—without his permission.

“He can’t tell me what to do!” I thought. I rarely broke the house rules, but in this instance, my passion outpaced my docility. My explanation was that I wanted the door to look “different,” “less boring,” and “stylish.”

But that fell on deaf ears, and my defiance angered my father. My punishment: missing my best friend’s birthday party to painstakingly scrub the thick layers of stripes with a paint stripper (that burned my nostrils and stung my eyes with tears) and then restoring the door to its original (and very unexciting) white.

“Do you know that your jeans are torn?” my father asked, his finger quivering slightly, suspended midair. “Why would you wear jeans with holes in them, anyway? Can’t you afford new ones?” His glasses slid down his nose, and he looked over the top of them, struggling to focus his eyes.

This time, half a century later from when I was judged and rebuked for painting a door, I didn’t feel embarrassed or self-conscious; I felt emboldened and confident.

“Dad, they’re supposed to be this way! That’s the style.” I shrugged and smiled back, tilting my head slightly while he gazed at me, looking confused, as if to say, “Here she goes again.”

I quickly changed the subject. “So, Dad, tell me about your activities today” was all I could muster.

My father is long gone. And if he were still alive, he probably still wouldn’t understand it anyway.

“Oh, I’d never wear ripped jeans!” declared my sister when she visited along with me that day. There’s slightly less than two years between my sister and me, but in many ways, we are worlds apart. “That’s for teenagers! I dress for my age,” she said.

Does that mean I don’t dress for my age? And what does “dressing for your age” really mean, anyway?

I don’t let my age strictly define me. Even when it sometimes has to. For instance, I recently became a grandmother. It’s the greatest bliss I’ve felt since my own two children were born more than 30 years ago.

But does being a grandmother mean I’m old or out of touch? It might have meant that in previous generations. But today’s grandmas are chic and cool.

I stay feeling young in other ways, too: by eating a mostly plant-based diet, walking everywhere I can, and working out frequently. I stay engaged in my life and try to learn something new every day. I returned to college for my master’s degree at age 50, accepting my diploma among my mostly 20- and 30-something classmates. I never want to stop growing and evolving.

I’ve always loved fashion. My younger self would sit down on Sunday nights and judiciously map out a daily schedule of outfits for the following week, careful not to repeat (horrors!) the same outfit for at least two weeks.

I don’t give in to all the trends, of course, but rather, like to mix them in to keep things interesting and, well, less boring. After all, nothing balances a pair of ripped jeans better than a tailored, crisp button-down shirt.

To be sure, I have a line. Sadly, no matter how flat my stomach or shapely my buttocks might be, I won’t wear a belly shirt or cheek-revealing denim cutoffs. And no matter how good my legs are, still, 10-inch miniskirts look wrong on me. Short skirts are still part of my wardrobe—just not too short (as dictated by me).

But ripped jeans? Why not.

I recently spoke with 72-year-old Lyn Slater, also known as the Accidental Icon, who has a broad social media presence in the beauty and fashion world. She gave me her thoughts on fashion “rules.”

“There are useless rules that have nothing at all to do with age,” Slater says. “I know 18-year-olds who would not wear a short skirt, and 70-year-olds with long legs who would. What we wear is personal and should be dictated only by ourselves.”

We have so many icons, if only we look. Betsey Johnson looks adorable and funky at 79. Diane Keaton, 75, has a quirky and cool personal style, replete with glasses and fun hairstyles. Blondie (aka Debbie Harry) is still blond at 76 (who cares if it might not be natural any longer) and looks great in both leather and a slightly more conservative silk dress.

Older doesn’t have to mean over the hill. We don’t need to shy away from bright, vibrant colors or fade into the background. We can make a statement, too.

My father, may he rest in peace, might not have understood my need, at age 10, to express myself with some defiance by coloring outside the lines. But now I know that the only person I need to please is myself.

When I gaze into the mirror, I don’t see a woman trying to be who she once was. I see a 66-year-old woman celebrating the person she has become.

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