Should You Dress Like Younger Coworkers?

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The NYT had an interesting “Ask Vanessa” question recently: should you dress like younger coworkers? Let's discuss…

In the NYT article (gift link), the writer asks Vanessa:

I work with many younger peers in a job that includes a lot of launches, dinners and parties. While I “dress” for these events, my peers remain in the jeans, knits and sneakers they wore all day. In this situation I advertise myself as a relic, no matter how well the clothes suit me. Are there ways I can embrace a more casual approach while also respecting the occasion? — Ali, Sydney, Australia

Vanessa Friedman, the NYT's fashion critic, tells her that age is a hard thing to completely bamboozle people over — no one will think you're as young as your daughters unless you're Kris Jenner. But, she notes, you want to lean into your age and the experience that brings… and dress as you please.

Should You Dress Like Your Younger Coworkers?

I do agree with this advice — presumably, with age you have earned the right to dress however you want to. This is why we often advise younger women just starting out to look to a midlevel for fashion guidance instead of the boss — because the boss can dress however she likes.

I also think that people are OK with there being an adult in the room in most circumstances for work events. Who's in charge? The person dressed the best (in a conservative sense) is often a safe assumption.

That said, there are a few nuances here that I think are interesting, and I'd love to get your thoughts…

Does Wearing a Sheath Dress + Heels Age You?

It's one of those things that is particularly hard right now because fashion has taken a decidedly casual turn in recent years — and a great example of this is the sheath dress + heels, which always used to be a safe outfit for conferences, networking events, and more, as well as the office.

In recent years I'm sure we've all attended events where most people wore jeans and blazers or something similarly casual (especially the young'uns), and there were a few women still in sheath dresses and heels. I will note at the getgo that I'm sure they looked fabulous — it's been a very safe choice for a reason, it's so easy to look polished and put together. But… did it age them?

I think that question is kind of irrelevant, honestly — the more important question is, did they look like they were out of touch? Did they look like they didn't know what year it was, or how current fashions were? I don't think so — I think those people in heels and a sheath dress probably kept their gravitas and respect and looked in charge. Could they have gotten away with jeans and a blazer and loafers and still looked polished and in charge (or, in a more conservative setting, a pair of wide legged trousers and a lady jacket)? Absolutely, but while also meeting the occasion.

Does It Matter How Big of An Age Gap There Is?

Here’s an important point: the smaller the age gap, the harder the question becomes.

If you’re in your early 40s, you probably came of age professionally in an era where a sheath dress, blazer, and heels were not just acceptable, they were the default uniform for looking competent at work. Many women built entire wardrobes around that formula, and it worked reliably for years.

Meanwhile, coworkers in their late 20s (and even early 30s) may have started their careers during or after the pandemic, when offices were already moving toward softer business casual. They didn’t “reject” formal workwear — they simply never adopted it. To them, the visual language of professionalism is different: trousers, knits, flats, and layers instead of suits and pumps.

So when the two groups meet at a work dinner or networking event, it can feel less like a fashion disagreement and more like a time-travel moment. Both groups are dressing professionally according to the rules they learned… but the rules aren’t the same.

The Real Issue: It’s Not Age… It’s Formality

I don’t think a sheath dress and heels automatically ages someone. What it can do, however, is signal a level of formality that no longer matches the environment.

For many years, the safest strategy was to dress slightly more formally than everyone else. Today, that can sometimes read less as “polished” and more as “out of sync,” especially in offices where hierarchy is flatter and approachability is valued.

In other words, the question isn’t:

“Do I look older than my coworkers?”

It’s:

“Am I speaking the same visual language as my workplace?”

Clothes communicate role, authority, and adaptability. When most of the room is in relaxed tailoring and you are in a full traditional professional outfit, the difference can stand out more than you intend — not because you look bad, but because the dress code has quietly shifted.

So What Should You Actually Wear?

The goal isn’t to dress younger. The goal is to dress current.

That does not mean adopting every trend your coworkers are wearing. It means updating the structure of your outfit while keeping your personal style and level of polish.

Some easy translations:

Instead of:

• sheath dress + pumps
  Try:
• column dress + flats or loafers + soft jacket

Instead of:

• suit + blouse
  Try:
• tailored trousers + knit top + structured sweater blazer or lady jacket (column of color!)

Instead of:

• blazer as the only finishing layer
  Consider:
• knit jacket, refined bomber, sweater blazer, or elegant cardigan

You keep the authority and polish, but you just remove the stiffness.

What You Don’t Have to Do

You do not need to:

• wear sneakers to professional events
• copy your younger coworkers’ casual outfits
• abandon tailoring or quality clothing
• chase trends that don’t feel like you

Vanessa Friedman is right that you won’t convince anyone you’re 26 by dressing like a 26-year-old. But you also don’t have to dress like it’s 2012 to look competent.

Professional style has moved toward “polished real clothes.” The sweet spot is clothing that looks intentional and current without looking like you tried to blend into a different age group.

A Useful Rule of Thumb

If you want a practical guide, try this:

Match the formality of the room, not the age of the people in it.

Younger coworkers are often unconsciously calibrating to workplace culture; they just started from a different baseline. When you adjust formality rather than copying specific items, you stay aligned with the environment while still looking like yourself.

And, in many situations, there is still value in being the slightly more polished person in the room… just not the only person dressed for a different decade.

Readers, let's hear from you. Have you run into this at conferences, recruiting events, or office dinners? Have you ever changed an outfit because everyone else showed up more casual (or more formal) than you expected?