Productivity Hacks

Sydney Sweeney Just Took Underwear-As-Outerwear Past the Y2K Whale Tail and Pulled a Thong Over Her Jeans

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Instagram/@sydney_sweeney

By January Nelson
January Nelson

The whale’s tail peeked out. Sweeney’s SYRN shot skips and tucks the cord without the denim.

Underwear as outerwear is not new. Madonna’s 1990 Blond Ambition tour put Jean Paul Gaultier’s cone bras and corsets on stage as costumes. The slip dresses of the 1990s kept blurring the line. In the early 2000s they pushed it in the other direction with the “whale tail,” high-rise jeans that were so slimmed down that the high-cut thong belt rode above the belt of Britney Spears, Paris Hilton, and Christina Aguilera.

Paris Hilton arriving at the Motorola event in Hollywood in December 2000
Paris Hilton attended Motorola’s Hollywood party in December 2000, an early witness to Y2K underwear. Photo by Chris Weeks / Hulton Archive via Getty Images.

Sweeney’s version skips the accidental look. In a photo posted on February 18 on Instagram promoting SYRN’s Playful collection, which went the day before, she wore a Kiss This Mid-Rise Thong pulled over her blue jeans, and a First Base Scoop Neck Bralette layered over a baby pink tee. Tongo does not look at anything. It is the top layer.

Sydney Sweeney rings the Opening Bell at the New York Stock Exchange with executives from American Eagle Outfitters
Sydney Sweeney rings the Opening Bell for American Eagle Outfitters on the floor of the NYSE in New York City on February 9, 2026. Photo by Spencer Platt/Getty Images.

SYRN launched in January with the Hollywood sign and the backlash that followed, and Sweeney, 28, has been a strong model for the label ever since. Playful drop sits on the same list as blouses worn as tops, corsets as outerwear, and new jeans sold with a fake waist belt sewn into the whale tail effect without underwear. Sweeney just went the most realistic way possible.

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About the author

January Nelson

January Nelson

January Nelson is a writer, editor, and dreamer. He writes about astrology, sports, love, relationships and entertainment. January graduated with a degree in English and Literature from Columbia University.



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