What Is Age-Appropriate Dressing?

From left to right, actress Michelle Yeoh, Martha Stewart and Queen Letizia of Spain.

By MyLittleBird Staff

PSST! Isn’t that a little young for her!? Can you hear your mother’s voice even when you’re the one having the thought? We’re not supposed to be so judgmental, right? This is the era of no rules? Uh-huh. But in Manhattan, where there is endless foot traffic, there are also endless variations on street dressing and rule-breaking. And when the spindly legs of an 80-year-old are sticking out from a miniskirt worn with a sassy teenager-worthy T-shirt, well, the buzzer goes off automatically.

These thoughts are prompted by a recent reader question to Vanessa Friedman, chief fashion critic of The New York Times: What are the rules for dressing as you age? One thought both Friedman and LittleBird Janet Kelly had: If you followed a trend (miniskirt, palazzo pants) back in the day, think twice, or more, about wearing it again. Then again, trends are constantly being tweaked and can certainly accommodate age. No?

Not everyone worries about being appropriate. Actress Halle Berry’s stylist put her in a see-through babydoll dress for last year’s Vanity Fair Oscar party. Could the fit, gorgeous 57-year-old carry it off? Sure. Should she have? Well, maybe one guiding principle should be, What image of myself am I trying to project? For Berry, maybe it was “babe with killer legs who can still pull off a sexy role,” in which case, Congrats.

The rest of us may opt for elegant, strong, serious or, at times, playful but with dignity. You probably cannot rid yourself of your mother’s voice in your head. And you can listen to it. But then, knowing who you are now, it’s up to you whether to heed or ignore it.

To illustrate how some women are balancing fashion and age, we looked at red-carpet pix and retail offerings of the moment. We sprang ahead into the spring 2024 runways for how to, and how not to, wear statement sleeves (FYI: An exhibit on big sleeves opens next Wednesday at the Museum at FIT in New York.) On the retail front, tulle skirts caught our eye and we came up with some ideas of how to wear two versions in a grownup, modern way.

But again, listen to your mother. Or not.

Photo by Rob Latour/Shutterstock

Janet: Prior to snagging the 2023 Oscar for Best Actress in her role in sci-fi, action film Everything, Everywhere All at Once, 61-year-old Michelle Yeoh attended the Oscars Nominees Luncheon in Beverly Hills wearing a Chanel pre-fall 2023 tweed pantsuit with a flared leg. It’s appropriately dressy for the occasion and for Yeoh’s athletic build. I have two quibbles: The pant legs are too long, and her Richard Mille watch is too big and sporty-looking to play well with this elegant suit. She’s an ambassador for the brand, so I guess we will forgive her.

Photo by Kristina Bumphrey/Shutterstock.

Nancy: In this red-carpet shot, Martha Stewart looks as if she’s apologizing for coming to the premiere of  the movie About My Father without first changing from her gardening clothes. This isn’t a case of age-inappropriateness but event-deafness. The color-coordinated peep-toe shoes suggest she was pretty definite about what she was doing. And the jogger suit would, I guess, be fine for a Saturday lunch with friends, but I don’t think she did herself any favors here.

Janet: It doesn’t matter what age you are, this olive green velour sweat suit is inappropriate attire to wear for a red-carpet walk at a film premiere in New York City. Except for those matching platform heels, I’d be tempted to think Martha was heading for the gym or an appointment with her masseuse or, as Nancy mentioned, Martha had no time to change out of her gardening gear. Even if unintended, it sends a snooty message that says I’m too busy and important to dress for this event.

Kathy: I bet her fancy chickens like it.

Photo by JJ Guillen/EPA-EFE/Shutterstock

Janet: Arriving at a meeting with the Spanish Association Against Cancer in Madrid, Spain’s Queen Letizia is ready to get down to business wearing a collarless white blouse, navy blue cardigan with pockets, trim black pants, kitten heels and handbag and computer. Her outfit is classic, appropriate for her age and the occasion, and yet totally modern. And that navy sweater instead of matching the other black elements, makes the whole look less serious. The white top lights up her face.

Nancy: In the dozens of pictures I’ve seen, Queen Letizia always looks trim and modern yet elegant and appropriate to her age and ceremonial station (there are many photos of gowns and regalia). Maybe it’s the lack of hats, but Letizia’s style is a refreshing divergence from the British royal family’s trappings (forgive me, I’ve just been catching up on The Crown). Maybe there’s a downside to not looking overly royal, but in terms of age-appropriateness, the 51-year-old Spanish queen is a model to follow.

Kathy: I’ve always liked combining black and navy blue so this combo suits me just fine. I’ve noticed Letizia pictured in an array of shirtwaist dresses and coordinates that don’t scream royalty, just good taste. Of course, on her sleek, slender frame a burlap sack probably would look swell. However, she doesn’t seem to lean toward flashy and I admire that. She sticks to an adult tailored look that also manages to stay fresh and modern.

Nancy: Here’s a design trend I can get behind: extravagant sleeve action. Interested in getting out of your Gap comfort clothes? A foray into the land of billowing sleeves can take you there without damage to your dignity.

Now, before you assume I’m getting behind the idea of the short-short denim outfit by Sacai, on the right, take a look at the more fluid, and arguably more wearable, version of the sleeve trend by Khaite, on the left. Easy-peasy (at least if you’re not height-challenged) and elegant.

I confess I love the architectural stiffness of Sacai’s denim sleeve—but as a savvy fashion editor pointed out to me eons ago, by the time some of these runway trends reach the sales floor of a department store, guided by buyers who know their customers, most sleeves will be scaled back and the butt-cheek-exposing micro miniskirts and shorts will probably be cut longer. And the Sacai top will be shown, and bought, with less-challenging bottom pieces. Keep the lower half of you trimmed back (like Khaite’s cigarette pants, on the left) and you wind up with an outfit that’s refreshing, appropriate for grownup girls and quite on trend.

Janet: Mega sleeves have been an enduring trend for the past decade. In this look (left) from her spring 2024 runway, Catherine Holstein, Khaite designer, played with proportion, balancing the billowy sleeves of a romantic peasant blouse with tailored black cigarette pants, a combination we grownup girls can pull off. Agree, Nancy. On the other hand, in this denim short suit (right) from Abe Chitose of Sacai, the top half is so circular and sculptural, it is almost a sphere shape that overwhelms the short bottom half. Balance matters, so we’ll see how this runway outfit morphs into something mere mortals can wear.

Nancy: Fair enough!

Kathy: Okay, Nancy and Janet. I’ll take your word for it, but these billowing sleeves, even if pared down, are too much for me. Realistically, how often would a person wear this look? Makes me think of Jerry Seinfeld in the Puffy Shirt episode.

Nancy: Ouch!

Janet: There’s something about tulle that appeals to my inner ballerina, the one who fondly remembers Carrie Bradshaw’s tiered white tulle skirt from Sex and the City. Both of these skirts above are from Anthropologie and sell for under $175. I’d pair the one on the left with a hip-length, structured matching blazer or jacket—and kitten heels—and wear it to a spring wedding. Another possibility is wearing either one with a leather jacket and boots for a bit of grit to balance the girliness.

Nancy: Here, after all these years, is Carrie Bradshaw’s tulle skirt but made for real women. It might be easier to pull off the graceful swish of the pleated mid-length skirt on the left—I see the look on the streets of New York all the time, on all ages of women. But toning down the top, as shown on the right, makes even the flouncier of the two skirts a possibility. Yes, it takes some grit, but age doesn’t have to rule this trend out. Just sayin’.

Kathy: May I please have them both?