What Does It Mean to ‘Dress Your Age’? (2024)

I have always dressed fashionably. I still want to, but, as I get older, I don’t want to look silly in an outfit for a 20-year-old. For example: Right now I’m wondering about pants. Everything seems to be really, really wide and ballooning. I like them, but they aren’t the most flattering. What about hemlines? Should they be long or short? Are there rules to dressing as you age? — Liz, Akron, Ohio

This is a question I ask myself a lot. After all, just because you can wear something doesn’t mean you should.

A few years ago, when I was watching a fashion show and saw a model in a tuxedo-shorts jumpsuit, I thought: “Aha! A tuxedo-shorts jumpsuit. That will solve a lot of black-tie problems.” Then, almost immediately, I thought: “Who are you kidding? You can’t wear that.”

Physically, the look would have fit me just fine (especially with tights), but psychologically I would have felt as if I were in a very fancy playsuit. And that’s the thing about that issue of “dressing your age.” It isn’t about a list of garments you can or can’t wear. It’s about all the associations and assumptions embedded in those garments.

Strict social or cultural rules about what to wear as you age don’t really exist anymore. The few that do tend to be contextual and institutional and have to do with workplace dress codes. And you don’t have to check a desire to be chic at the door of, say, 50. Just because fashion still insists on showing clothes on bodies under the age of 25 doesn’t mean those clothes aren’t actually meant for women twice that age.

But how you dress is a statement about who you are and how you want to be perceived. And that changes as we grow up — even more, sometimes, than our bodies or dress sizes (though those, of course, change, too).

Personally, I feel like my years have been hard won, and experience is worth wearing. Which means I have said goodbye to clothes I generally associate with my youth: hemlines above my knees (especially attached to skater and rah-rah skirts), tops that show off my belly button, ruffles, slip dresses. Anything, really, that takes me sliding down a wormhole into an era when I was a much less formed person, or one that I lived through once already. That has as much to do with personal associations as it does with actual years.