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 our 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.

One good role model for this style is Catherine, Princess of Wales, perhaps the ultimate former proponent of skinny jeans and riding boots (or ballet flats), who has managed to wean herself off that look, at least part of the time, in favor of suit jackets with a longer line, semi-flared trousers and court shoes. She looks grown up and comfortable, as if she can just get on with life.

Then consider adding some classic outerwear, like a swishy trench coat or a neat car coat. And, per Mr. Do, layering: a pleated skirt over tailored trousers, for example, or a very long white shirt or dress (he made a great one in his Banana Republic collaboration) worn unbuttoned from the waist over slouchy pants.

The point is to adapt a wardrobe, not abandon it. After all, the one approach to dressing that will immediately identify you as up to the minute is to start with sustainability in mind. And there is nothing more sustainable than thinking of whatever you wear, and buy, in the most long-term way possible — for this generation and beyond.

Your Style Questions, Answered

Every week on Open Thread, Vanessa will answer a reader’s fashion-related question, which you can send to her anytime via email or Twitter. Questions are edited and condensed.