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Kaia Gerber getting out of a car at the Olivia Rodrigo concert at MSG.
Photo by Jose Perez/Bauer-Griffin/GC Images.

Kaia Gerber has mastered the art of model-off-duty style. Her wardrobe is packed with timeless staples—with a few fun pieces thrown in. And that combination leaves all of Kaia Gerber’s outfits looking effortlessly stylish. She pulls off bucket hats, blazers, and breezy dresses with ease, throwing together outfits chic enough to bookmark and save for later. If there’s an intimidating trend you’re interested in trying, Kaia Gerber’s street style looks are the perfect place to turn for inspiration. She’s probably already worn in, showing us all how to style it with basics we already have in our closets.

Case in point? Kaia Gerber showed up to Olivia Rodrigo’s Guts Tour in New York City wearing two controversial Y2K trends we never thought we’d see again. In true Kaia Gerber fashion, she pulled both off and made the once-regrettable 2000s style choices look refined and expensive. Seeing Kaia flawlessly experiment with these trends makes us want to dust off our favorite aughts accessories. Any outfit she wears screams downtown cool girl, and this look is proof that even when trying out daring trends, Kaia manages to maintain her signature minimalist style.

We shouldn’t be surprised. The fact of the matter is, Kaia has a way of making the most basic pieces—and the most bizarre ones—look fashion-week-ready. The model knows that finding good staple pieces is the key to having a versatile yet stylish wardrobe. Paired with the right essentials, even the most unexpected pieces can look cool.

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