Ever wondered whether you should dress more casually like your younger co-workers – jeans, knits and sneakers, well, here's something to think about.
First of all, you are going to look different from your younger peers no matter what.
Maybe not if you are Kris Jenner and get refreshed by Dr Steven Levine and come out looking like your daughters, but for most of us, this is a simple reality of age. No style of clothing is going to fool anyone.
So the real questions here are: Why the concern about standing out, and is it worth trying to dress to fit in at all?
The employment market is scary. And there is a world in which looking old or, more important, looking like you are stuck in older ways, becomes a handicap. It suggests you can’t keep up with technological advances.
AI! In that context, dressing like a fogy could plant subliminal cues that might work against you in an office reorganisation, or layoffs.
Conversely, if you wear clothes that make you feel uncomfortable or awkward, you’ll probably telegraph a similar message, and that won’t be good, either.
Read more: Are jumpsuits still fashion-forward, or is it time for a wardrobe change?
If wearing, say, jeans and sneakers to a work event makes you feel like you are faking it, those around you might also get the sense that you are faking it.
That undermines the image you probably want to convey, which is that you really know what you are doing.
An attribute that generally comes (duh) with age.
In fact, the best solution may be to lean into your age and the experience that brings. It is, after all, the thing you have that your colleagues presumably don’t.
That means dressing the part, which just means dressing as you want.
If spiky pumps make you feel elegant and confident and help you walk into a room, then wear them, even if everyone else is in Chuck IIs.
They will be a subtle reminder to those around you that you bring a different, valuable perspective to the table. Not to mention attention to details.
Besides, you don’t have to completely transform to “dress up”.
Read more: What are snoafers – and did the trend turn out to be a fashion misstep?
If you normally wear a jacket with a button-up, consider swapping the button-up for a T-shirt, but choose one, as well as the jacket, in a plush material like silk or velvet.
You can wear jeans, but rather than faded denim, opt for tailored dark denim – or maybe some generous tweeds (channel Katharine Hepburn).
Wear a knit like your colleagues, but one with some beading or metallic yarn for shine. You might be surprised at the reaction.
Never forget the 2015 film, The Intern, in which Robert De Niro plays a 70-year-old “senior intern” at an etail startup staffed largely by 20-somethings wearing T-shirts under unbuttoned shirts and jeans, or crew necks (this was before the time of the quarter-zip).
In one scene, De Niro’s character shows up every day in his customary suit and tie, just as he did in his previous career.
When told by the chief executive that he doesn’t have to because “we’re more cazh (slang for casual) here,” he simply says, “I’m more comfortable in a suit.”
For him, it... well, works. – ©2026 The New York Times Company/Vanessa Friedman
This article originally appeared in The New York Times.
