The Divisive Y2K Trend Taking Over Celeb Street Style—Here’s How to Wear It

The latest controversial fashion trend to take over city street style? Skirts over pants. You heard that right.

Millennials may remember this polarizing layered look from Disney Channel’s early and mid-aughts era, but celebrities are showing us that the outfit combo can look chic in 2026.

Instead of sequins and bootcut denim (yes, we’re referring to that 2005 Ashley Tisdale red carpet look), stars including Dua Lipa, Shakira, Anne Hathaway, and Myha’la are opting for sleek silhouettes, top-notch tailoring, and unexpected pairings.

• The skirt over pants pairing peaked in the early and mid-2000s, with stars taking a maximalist approach to the trend.
• In 2026, stars like Kendall Jenner, Jennifer Lawrence, and Kaia Gerber are styling the controversial combo in a modern way.
• Built-in styles that combine skirts and pants into one piece are the best way to avoid extra bulk.

How to Rock the Skirts Over Pants Trend in 2026

While the skirt and pants pairing of the 2000s was all about maximalism, these days, celebs are taking a more subtle approach to the trend. Think solid hues, streamlined designs, and modern textures for an elevated feel.

Or you can also take a page from Industry’s Myha’la’s book with a voluminous midi skirt and patterned pants for a whimsical feel.

They make the ideal summer-to-fall transition piece, too. Wear them with a lace trimmed satin cami in the summer and a sleeveless turtleneck in the fall.

Because layering a skirt over pants can often look a bit bulky, it’s best to opt for built-in styles that combine skirts and pants into one piece.

With the celebrity nod of approval, are you ready to rock the daring combination?