Should brands lean into millennial cringe?

"Just this week, GQ called out Supreme for resurrecting "another cringe 2000s trend", after the brand re-issued its brimmed beanie, once beloved of Fall Out Boy bassist Pete Wentz. Wired headphones (like those in the iPod ad) continue to be an It-item, beloved by stars like Addison Rae. Meanwhile, Taylor Swift - who's made a career out of her sincerity - announced her engagement with a series of twee, floral photographs."

"They were wildly successful, helping to catapult songs like Feist's '1234' and the Ting Tings's 'Shut Up and Let Me Go' to the charts, as well as selling hundreds of thousands of iPods. But today, their carefree vibe may be classed as 'millennial cringe', Gen Z's term for the raw earnestness of the late 2000s and early 2010s, which has been seeping back into popular culture in recent months."

Late-2000s millennial sincerity—raw, emotional, and un-self-aware—has resurfaced across fashion and pop culture. Early-2000s cultural artifacts such as Apple's iPod ads, wired headphones, and brimmed beanies have regained visibility among celebrities and brands. Taylor Swift's romantic, floral engagement imagery echoes the twee aesthetic of the period. Gen Z often labels this aesthetic "millennial cringe" and mocks its earnestness, while cultural debates—like those around the song "Home" by Edward Sharpe and the Magnetic Zeros—reignite conversations about authenticity. As consumers grow tired of pervasive cynicism and internet shorthand, brands can leverage this renewed sincerity as a compelling marketing approach.

Read at Vogue Business