How Can I Update My Millennial Style?

Now that I’m finished having children and my size is stable, I would like to invest in a quality capsule wardrobe, one that works every day and can easily be dressed up for the occasional work presentation or meeting. Here’s my problem: I am stuck in a millennial sense of fashion — tight jeans, a looser top, cardigans and ballet flats or riding boots. What’s the easiest way to update my style? — Jen, Columbia, Md.

Gen Z has been mocking millennial style with so much glee in the last few years that doing so has become its own TikTok trend. But seeing this as a generational issue is, it seems to me, a mistake. It’s more of a decade issue in that our style is often formed by the ethos of the time in which we came of age, started buying out own clothes, and had to figure out what it meant to navigate identity in the outside world.

I’m not sure when that thinking was reduced to a monolithic generational stereotype — probably around the time Gen X started trying to distinguish itself from baby boomers, and then millennials came along — but this kind of categorization hasn’t done any of us any good.

That said, there is a very simple solution to feeling as if your wardrobe dates you, and it is not chasing the next hot (young) thing — or retreating to the frumpy thing. Do not fall into either trap.

In fact, do not think in terms of time periods and their fashion. What is au courant today is passé tomorrow. Rather, think in terms of clothes that are timeless. And how they may adapt to your own sense of self.

For example, while I would never tell you to give up your skinny jeans entirely — as far as I’m concerned, jeggings aside, they now count as a classic — every designer I asked about updating a wardrobe, including Peter Do, the millennial designer for Helmut Lang, and Tommy Hilfiger, came up with the same answer: looser pants. But not all looser pants are created equal.

Rather than going straight to giant cargo pants and feeling as if you have gone straight down a rabbit hole to the 1990s (a.k.a. Gen Z’s favorite decade they missed), try easing into a higher-waist, more tailored style. Think Katharine Hepburn instead of Britney Spears. Pair those pants with a boxy knit — a silhouette that was all over the Theory collection I just saw — or a blazer as opposed to a tank top or a little cardigan.

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