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

By

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

The whale tail peeked. Sweeney’s SYRN shoot skips the peek and wears the thong on the outside of 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 clothing. The 1990s slip dress kept blurring the line. The early 2000s pushed it the other direction with the “whale tail,” low-rise jeans cut low enough that a high-cut thong strap rode above the waistband on Britney Spears, Paris Hilton, and Christina Aguilera.

Paris Hilton arriving at a Motorola party in Hollywood in December 2000
Paris Hilton makes her entrance at Motorola’s Hollywood party in December 2000, an early front-row witness to the Y2K underwear-as-outerwear moment. Photo by Chris Weeks / Hulton Archive via Getty Images.

Sweeney’s version skips the accidental peek. In a February 18 Instagram photo dump promoting SYRN’s Playful collection, which dropped the day before, she wore the Kiss This Mid-Rise Thong pulled on over her blue jeans, with the First Base Scoop Neck Bralette layered over a pink baby tee. The thong isn’t peeking out of anything. It’s the top layer.

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

SYRN launched in January with the Hollywood sign stunt and the backlash that followed, and Sweeney, 28, has been the label’s steadiest model ever since. The Playful drop sits in the same lineage as bralettes worn as tops, corsets as outerwear, and the newer jeans sold with a fake thong waistband stitched in for the whale-tail effect without the underwear. Sweeney just went the most literal route available.

Thanks for spending time with Thought Catalog. Connect with us on Facebook and browse the rest of our website.

Read more Gossip.

About the author

January Nelson

January Nelson

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