How to Wear a Y2K-Inspired Maxi Skirt Now, According to a Stylist

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Those last weeks of summer and early weeks of fall can be weird, weather-wise: The lingering humidity will have you automatically reaching for the mini skirts, while the evening breeze will have you wanting more coverage. And short hemlines have had such a hold on fashion for the last few years, they’ve become a sort of default in styling. However, the pendulum seems to be swinging in the other direction, with longer skirts emerging as a seasonless piece suited for a range of occasions and forecasts.

“I love the fact that maxi skirts can be sexy while still possessing a sense of mystique,” says stylist Mickey Freeman, who works with celebrities for red-carpet and editorial projects. “This versatile piece can be incorporated into a look appropriate for any of the four seasons.”

Unsurprisingly, we can thank the Y2K trend for the maxi skirt’s resurgence. Freeman has noticed a few key features from that era’s styles that remain in 2023, such as strategically-placed slits and styling with chunky ankle boots and a midriff-baring tops. It made a powerful statement then, and it still has that impact now.

“On the music video for ‘Are You That Somebody,’ Aaliyah debuted a highly-slit black maxi skirt, complete with a cropped top and sheer bolero that was the perfect segue into a sexier and more mature image for the entertainer,” Freemans offers as an example.

That’s the energy we’re bringing for all of our fall outfits. Scroll through for some stylist-approved ways to wear a maxi skirt.

How to Style a Denim Maxi Skirt

For a denim maxi skirt, Freemans favors a look similar to the one he styled Keke Palmer in for a 2019 Paper spread: “a classic white dress shirt tied with a front knot to create a cropped look,” paired with white cowboy boots and finished with oversized, chunky jewelry. Just add a day coat.

DL1961 Asra Low-Rise Denim Maxi Skirt, $239, available here (sizes 24-31)

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How to Style a Cargo Maxi Skirt

To offset the utilitarian feel of a cargo maxi skirt, the stylist suggests “a dainty semi-sheer or lace top to create a look that exudes ‘brick and lace.'” You can top it off with a fitted bolero, which “can add dimension without drowning out the top,” he adds. “A raw hemline can add an interesting and edgy element needed to complete the look.”

Garage Poplin Parachute Skirt, $60, available here (sizes XXS-XL)

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How to Style a Maxi Slip Skirt

You already knew that slips act as a perfect anchoring piece in an outfit. They also serve as a great foil for the fluttering ruffles that are currently having a moment. Metallic finishes add some additional texture.

Retrofête Silvana Silk Maxi Skirt, $378, available here (sizes XXS-XXL)

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How to Style a Printed Maxi Skirt

When styling a printed maxi skirt, Freemans favors a coordinating set. “Even after going through hell and water, finding a two-piece set with a matching print would be the route that I would want to take to accentuate the entire body, as opposed to just its bottom half,” he says.

Tia Adeola Read All About It Set, $250, available here (sizes XS-XL)

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How to Style a Low-Rise Maxi Skirt

A low-rise maxi skirt may sound daunting, but Freemans insists it’s all in your choice of top. “I like to use a low-rise maxi skirt with a cropped top to flatter the midriff, or a corseted top for those who prefer coverage,” he says. “The skirt itself and jewelry lend movement to the overall look.”