The Y2K celebrity off-duty look is back in new ways for resort 2027.

Think track pants, baby Ts and athletic jackets mixed with ultra-feminine layers and accessories, made famous by the likes of Madonna and Victoria Beckham’s early 2000s wardrobes. Now designers are mixing well-known athletic silhouettes with girly details such as bows, pastel hues and playful prints to evoke a new take on sporty femininity.

Since last summer, Madelyn Somers’ Made Some Sportswear has been on fire for her meld of vintage novelty and vacation travel style, as seen through her viral beach-to-street board shorts. Since then, she’s expanded into board short-inspired miniskirts, pullover jackets and pants, which continue to push the off-duty, sporty-meets-girly look into new territories. The same can be said of Sandy Liang, who continues to be a leading contemporary designer driving the trend.

“I love the idea of like the gorp-y, dorky jackets that we all were forced to grow up wearing. That’s kind of the same language of why I started doing fleece [jackets] — like those fleece-lined windbreakers from Old Navy, that, yes, were hideous but now cool,” Liang told WWD of her resort collection, which features a strong new selection of sporty shrunken anorak jackets and heavier parkas in candy-colored hues with back-bow motifs.

Elsewhere, Amy Smilovic took her signature pragmatic approach to the season’s look by whipping up new takes on mainstay nylon layers with brightly colored poufed peplum “skirts” styled over casual cashmere blend T-shirts and sporty zip-up jackets with matching skirts.

Here, WWD spotlights the girly-meets-sporty trend from the contemporary collections, as seen from the likes of Sea, Made Some Sportswear, Alémais and Tanner Fletcher, alongside buy-now styles from NikeSkims, Gimaguas, Guest in Residence and more.

Styled by Emily Mercer

Model: Leah Simon at NY Model Management

Hair by Charles McNair

Makeup by Ashley Ciucci

Associate Market Editor, Ari Stark