Stacy and Clinton Break Down the Style of When Harry Met Sally episode artwork

EPISODE · May 19, 2026 · 21 MIN

Stacy and Clinton Break Down the Style of When Harry Met Sally

from WHY'D THEY WEAR THAT? · host Simple Alien

In this episode of Why'd They Wear That?, Stacy London and Clinton Kelly revisit When Harry Met Sally and break down the film's fashion across twelve years of changing style. From Sally's preppy late 70s looks and early yuppie polish to oversized denim, off the shoulder party dresses, wedding fashion disasters, and Harry's truly unfortunate sweaters, they unpack how the wardrobe reflects real people living through real time. This is less about high fashion and more about character, era, and the kind of styling that quietly supports one of the most famous romantic comedies ever made. Special Thanks to Our Sponsor: The Knickerbocker Hotel → A legendary New York landmark reborn as the first luxury hotel in Times Square. https://www.theknickerbocker.com/ Produced by Simple Alien → https://www.simplealien.com/ Camera, Audio and Crew provided by TV Boy → https://tvboynyc.com/ About Why'd They Wear That?: A pop-culture and fashion commentary show where Stacy London and Clinton Kelly break down the on-screen looks that sparked trends, started debates and occasionally made audiences ask, "Why'd They Wear THAT?" → https://www.whydtheywearthat.com/ Find out more @ ALL CHEWED UP Channel → https://www.allchewedup.com/

Episode metadata supplied by the publisher feed · Published May 19, 2026

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Stacy and Clinton Break Down the Style of When Harry Met Sally

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