What’s Someone My Age ‘Supposed’ To Wear? Older Women Share Their Thoughts

When I look at photos of myself from 20 to 30 years ago, I realize that I had no idea how good I looked. I never thought twice about wearing short skirts and dresses when I was in my 20s, 30s and even 40s. I’m now in my early 50s.

Recently, I tried on some of the things in my closet and deemed them “too short” — not something a younger me would have ever done. That got me thinking: How short is too short when you’re a half-century old or more? Is it different than when I was 22? Should it be different? How else have my style and fashion choices changed as I’ve aged?

I became intrigued by the answers to these questions — if there were answers, and if those answers even mattered — as well as the thoughts, worries and fears that other women my age have about their fashion and style choices. So I spoke to as many of my peers as I could, and also got insight from a psychologist. The stories and conversations we had were illuminating, validating and wonderfully insightful.

I’ve known Natalie Flores, age 49, for about 25 years. We worked together when we were in our 30s and became close friends. Those were the days of short skirts, tank tops and cowboy boots in Austin, Texas. Bare legs and arms were our norm. Though I have since moved to a place much less swampy, Nat still lives that state. Some of her fashion choices have changed, though.

“I no longer wear shorts because of the way my inner thigh curves, although I have no problem with a short skirt because it hides that inner thigh curve,” she told me. She also said she no longer wears cap sleeves because they “point” to a soft and pale inner arm that she’d rather hide (from both her own reflection and the public).

Joan, a 69-year-old cyclist and retired lawyer who requested to keep her surname private, told me that since she passed the 50-year milestone, she no longer wears miniskirts.

“I stopped because I just didn’t feel like showing off that much anymore — didn’t feel the need to advertise, as it were.” she said. “As I got older, no skirts whatsoever. Didn’t like stuff flapping around my legs. Besides, if I dropped something or had to climb over something, I didn’t want the hassle of a skirt. Both of those things happened in my 40s and 50s.”

Stephanie Ruksyio, a 50-something French woman I met a couple of decades ago in a bistro, had an effortless, sexy style that I myself was never very good at. When we talked, she told me that her style has definitely changed, and that she feels as if she is still undergoing changes, both fashion and otherwise. This, I think, is a state we should all aspire to: perpetually growing and becoming. I mean, are we ever really done?

“The wonderful thing is now I don’t have any pressure or drive to impress,” Stephanie said. “My fashion and style decisions have gradually become … comfortable yet funky, but above all true to myself, instead of hypothetically pleasing the times and/or people. I feel and love my age in the sense that I dress completely in tune with my needs and wants, regardless of exterior inputs.”

Some of the women I talked to lamented that their skin has begun to sag. Joan told me that despite her good muscle tone and the fact that she is in great shape, the packaging is sagging.

“Unfortunately,” she said, “gravity has been around as long as I have. That one breaks my heart.”

Jeannie Barbato, a 70-year-old woman who is also active and fit, said something similar: “I am more aware of showing skin — wrinkly neck and arms, legs that are increasingly scarred and mottled. But, not infrequently, I do it anyway.”

“If a lot of your self-esteem is based on your appearance, you’re going to have more anxiety as you get older because your appearance changes. And I think this is especially true for women,” Ann Kearney-Cooke, a licensed psychologist and wellness coach in Ohio, told me.

“You need to define yourself by the choices you make each day, not what’s happened in the past or how culture’s perceiving you,” she said. These include deciding to be a better person or a better friend, to eat healthy, to move, to experience the arts.

“Focus on the choices you make to feel good about yourself and your body,” she added. “You get affected about a lot of things, like who your partner is, what fashion has meant in the past to you, how important people in your life dressed.”

At the end of the day though, the trick is just finding colors, fabrics and styles that look good on you, that you feel good in, that really express who you are now.

“A gift to getting older, I think, is that we’re more clear about who we are,” Kearney-Cooke said.

Thankfully, as I’ve gotten older, I care less about what other people think of the way I look. Not that sometimes I still don’t worry about how I’m perceived, but ultimately I am better about not giving those kinds of concerns much credence. One person responded to my miniskirt question by saying: “No worries. No fear. I wear what I want.”

And when it comes to the gaze of others, there’s a certain freedom to be found in acknowledging that not everyone is watching you. “I look at other women my age and think, nobody cares how we dress anyway, which also gives me a certain amount of carefreeness,” Jeannie said.

Natalie told me that she’d recently been feeling nostalgic for her college years look and questions whether she’s trying too hard to look young.

“I have been experimenting on adding elements of that look to my choices. And I definitely pause and wonder if it looks forced, if it makes me look like I’m trying to look younger or if I look out of touch with what someone my age is ‘supposed’ to wear,” she said.

Many of us spend a good deal of time worrying about how we look and whether we will appear attractive to others. And this, of course, is always tied up in how we choose to dress, as well as our relationships with our own bodies, Kearney-Cooke said.

“We also have to teach people how to talk about our bodies,” she said. She told me a story about one of her clients who received a clean bill of health from her doctor. The woman was very pleased, but when she told her husband, he asked if the doctor had said anything about her “big butt.”

“And this is the best part,” Kearney-Cooke told me. “The woman replied, ‘No, he didn’t ask about you.’”

A big part of accepting aging is the maturity that comes along with it. As Stephanie put it: “It’s a hard-won freedom to disregard how one is perceived by others. And I, for one, am so grateful to all who were pioneers in carving the road to openly expressing oneself unapologetically.”

“When I was younger, I had no idea how good I looked,” Joan said. “No one does. But then you get older and you look at pictures of yourself when you were young, and you think: ‘Jeez, I really looked great. I wish I’d appreciated that more and stressed less.’”