Hailey Bieber, low-rise jeans, and a CD player blasting The Cranberries: Gap is once again turning up the nostalgia dial, reviving its late ‘90s and early aughts aesthetic for a new generation of shoppers. Yes, 1996-born ‘Zillenial’ Bieber is her usual effortlessly cool self, and yes, the denim is trendy; but that’s not all Gap is selling.  The brand has mastered the art of monetizing the "millennial ache”—nostalgia for the pre-algorithm era and the pop culture and fashion that defined it—with ads that nod to its Y2K heyday, fronted by Gen Z favorites like Troye Sivan and Katseye.  The strategy is working. In Q1, Gap Inc. CEO Richard Dickson attributed its 10% sales boost to the brand’s “culturally relevant storytelling,” which has won over millennials and Gen Z in the last 18 months. Fresh research from music video platform Vevo shows it’s actually Gen Z leading the Y2K resurgence. Sixty-six percent of the demographic (born between 1996 and 2010) feel “borrowed nostalgia” for times they didn’t live in, compared to 55% of Millennials and 54% of Gen X. Laura Vanison, Vevo’s vp of research and measurement, said the endless online scroll is fueling this appetite. “Gen Z audiences have immediate access to so much content that, ironically, everything can feel fleeting,” she told ADWEEK. By discovering or reliving vintage moments, they can feel that sense of community, making nostalgia “core to their media diet.”  When brands harness this in a way that feels natural, as Gap’s nod to the ‘90s does, it can strengthen emotional connections with consumers by 22% and increase re-engagement by 17%, according to Vevo’s “Then is Now” report — which surveyed more than 1,800 Gen Z, Millennial and Gen X consumers across the U.S., U.K, and Australia. Reviving Y2K icons for a new era While Gap jumped on Gen Z’s longing for Y2K early, others have followed suit. Some of the biggest success stories come from brands that were icons of the era themselves, like Coach. Under CMO Joon Silverstein, Coach has revived its 2003 Soho shoulder bag and expanded its (Re)Loved vintage program. Bella Hadid and Charli XCX have embraced the styles.  As a result, parent company Tapestry revealed in its Q3 earnings, so too has Gen Z. The cohort accounted for more than 35% of the company's 2.4 million new customers in the three months to March, when Coach generated $1.7 billion in revenue—up 29% year over year.  Ahead of her tour, Bath & Body Works recently tapped Millennial icon and Lizzie McGuire star Hilary Duff as a creative partner and brand ambassador to promote its Gen Z-coded fruit and fusion range. In the same month, Pizza Hut put its own spin on Y2K nostalgia marketing with a throwback value menu featuring ‘90s and ‘00s classics, like $3 personal pan pizzas and s'mores sticks. It also launched a capsule collection inspired by vintage Pizza Hut uniforms.  It’s all part of its broader “Hut Originals” strategy to tug at Millennial heartstrings and bring Gen Z into the brand. Pizza Hut CMO Melissa Friebe told ADWEEK this playbook is carefully backed by “decades of cultural relevance,” from the chain’s red dining booths to the role it's historically played in family celebrations. “For us, leveraging nostalgia feels earned, and not like something we’re trying to create from scratch,” she explained. Nostalgia trip  Bath & Body Works and Pizza Hut’s results won’t be fully baked until next year. But for Lisette Sand-Freedman, co-founder and chief Visionary officer at Shadow, Y2K reboots aren’t a shortcut to success.  “It only gets you so far,” she said. “We advise clients not to mistake familiarity for relevance. As more brands lean into throwback references, the brands that stand out won’t simply recreate the past; they'll use the reference to create something entirely new, to connect to existing audiences or to invite new audiences in.” Her agency is responsible for E.l.f’s Judge Judy-fronted work targeting Gen Z. For that one, she said, “nostalgia opened the door,” but it was cultural relevance that kept people talking. Nicole Stetter is head of social at L.A. creative agency Saylor, which has built campaigns to introduce Gen Z to franchises including Disney’s Goosebumps series. She said what gives brands like Gap, Coach, and Pizza Hut leverage is their emotional tug: the idea that younger generations can experience the “magic humility of Y2K” through a product or service. “You may not have been in elementary school when Pizza Hut gave out free coupons for cute little individual pizzas because you finished reading a book, but you can relive some of that quaint simplicity by joining their rewards program today,” Stetter said.  “And in a world where ‘doomscrolling’ is at the forefront of the lexicon, who doesn’t want an escape to simpler times?” she asked.