It’s impossible to imagine Cher without Bob Mackie, or Madonna sans Gaultier. Despite all the talk about “Hollywood hair theory,” generational talents are just as easily defined by their clothes. And these days, pop stars’ looks are directly tied to their entire act: both their “eras,” and the universes they create where their music (and fans) live. It isn’t a coincidence that Gen Z’s preeminent pop faves—Chappell Roan, Charli xcx, Sabrina Carpenter—reached new echelons of stardom following drastic shifts in image. It’s Law Roach’s principle of “the right girl in the right dress.”
“People like Prince, David Bowie, and Björk created an entire world and stayed so true to that world within everything that they did, not only sonically, but visually,” Roan’s stylist, Genesis Webb, tells W. “It’s how you let people know how to feel.” In 2026, that translates to both IRL and online personas, which call for special and eye-catching looks. Webb herself is a world-building whiz, having successfully lent a more refined eye to Roan’s wardrobe. Not long after dressing the “Pink Pony Club” artist for a series of headline-making festival performances in the summer of 2024, sales for her album The Rise and Fall of a Midwest Princess—which had debuted nearly a year earlier—skyrocketed.
Webb and Roan have tapped into their mutual reverence for drag and Club Kid culture to create viral fashion moments, such as the singer’s Statue of Liberty-inspired look at Governors Ball in 2024. The stylist collaborated with fetishwear designer Monique Fey to reimagine the sculpture’s signature toga in latex, leading to raucous applause when Roan turned around to reveal her bare buttocks peeking through a cutout in her skirt. Such hijinks recall the era of Madonna’s Blond Ambition Tour, when she famously ripped off her pantsuit to showcase a satin leotard complete with conical cups, devised by a then lesser-known designer by the name of Jean Paul Gaultier. But reinterpreting the familiar is key to creating a sustainable image, adds Tyla’s stylist Ron Hartleben. He frequently works with vintage and archival fashion, looks made before his client was even born. Case in point: Tyla’s Tom Ford for Gucci minidress at the CFDA Awards. Donning rare pulls on the red carpet is no newfangled thing, but when creating an entire universe around a pop girl, nostalgia can be a potent ingredient to add to the mix.
“Wearing historical pieces puts talent in new lights, and it invites them to be examined in a different way. It’s a more intellectual approach to clothes rather than just wearing the shiniest, newest thing,” Hartleben says. “Adding that level of knowledge with looks is always going to propel any talent’s star power, because there’s more depth to the outfit than we’re realizing on the surface.”
He also played a major role in Carpenter’s reinvention, having dressed her for the “Feather,” “Espresso,” and “Please Please Please” music videos. His styling work was instrumental in ushering Carpenter out of her teeny-bopper phase. “She wanted to have a new visual language that was a little bit more fashion-forward, playful, and tongue-in-cheek,” Hartleben says.
Sabrina Carpenter during her Short n’ Sweet tour in 2024.
Carpenter, a former Disney Channel idol, had a solo career for some time before the release of “Feather,” but the chart-topping track marked her first true taste of mainstream success. When the video generated controversy after the singer danced scantily clad around a church—in frou-frou Carolina Herrera tulle, no less—it primed Carpenter for her musical coming-of-age, which would culminate with the release of her breakthrough album, Short n’ Sweet.
Old Hollywood and pin-up silhouettes were motifs Hartleben and Carpenter sought to repackage for a younger audience. Although she now works mainly with stylist Jared Ellner, this concept continues to guide much of Carpenter’s wardrobe today. Take her rhinestoned bodysuits and négligées from the Short n’ Sweet Tour, for instance: these modern riffs on vintage lingerie were designed by Victoria’s Secret, a newer brand that simultaneously sparks nostalgia for Gen Z.
As children of the 2000s, the decade’s aesthetics are sources of inspiration for pop’s new guard. Cartoons and dolls of the period, such as Winx Club and Bratz, are cited by Zara Larsson’s stylist, Caterina Ospina, as sartorial influences, while Hartleben has dressed Tyla in Rock Revival, a noughties mall brand akin to True Religion and Affliction.
“Y2K was a moment in time that was all about freedom and taking sexual liberties with clothes, feeling empowered in your body and taking risks without being scared of being labeled as slutty or tacky,” Hartleben explains.
Ospina echoes this sentiment when she describes her approach to working with Larsson, whose star has only risen since the release of her album Midnight Sun and her tour of the same name.
Zara Larsson performs on November 5, 2025 in London.
“Zara’s style transmits this feeling of being sexy and free, that you can be anyone or anything, and people love her for that,” Ospina says. “She’s not dressing for any gaze specifically, she’s just dressing for herself.”
The same could be said of any pop talent du jour, from Rihanna to Beyoncé and Lady Gaga. These particular artists inspired Tyla, Larsson, and Roan as they’ve forged musical careers of their own. It’s why paying homage to one’s cultural predecessors is another trick of the pop star stylist’s trade.
Tyla nodded to Aaliyah at the MTV European Music Awards in 2024, rocking a fur-trimmed Roberto Cavalli gown printed with the label’s trademark tiger stripes. She also wore a teal version of the dress, which Aaliyah originally sported in yellow at the MTV Video Music Awards in 2000.
Tyla at the MTV EMAs in 2024.
These memorable visual cues aren’t always reinterpreted so literally. Roan, for example, captures Lady Gaga’s style ethos without ever directly referencing her: it’s in her choice of designers (like Alexander McQueen, who cited Gaga as a muse) and her ability to tell stories with clothing. Webb separated Roan’s looks at the 2024 VMAs into three acts, not unlike how Gaga traipsed up the steps at the 2019 Met Gala while shedding layers of Brandon Maxwell satin.
“It’s more about capturing the same essence of what was so captivating about those artists,” Hartelben explains of his strategy, a point of view that Ospina and Webb also share.
Chappell Roan at the Grammy Awards on February 1, 2026.
Homing in on elements that set one apart are crucial. Larsson is hardly ever seen without a hibiscus blossom, while Tyla often flips the waistline of her jeans, wearing them unbuttoned.
Tyla in Paris on January 28, 2026.
This, combined with a stylist’s knowledge of emerging trends—read: Larsson’s keychain miniskirts and Tyla’s reimagining of a ’90s Chanel top as a dress—is how artists can establish themselves as distinct personalities.
Uniqueness is also achieved by collaborating with independent and emerging designers, like Zana Bayne, in Webb’s case, who crafted a full set of leather armor for Roan’s VMAs performance. Ospina, meanwhile, has tapped the talents of Sorcha O’Raghallaigh to create sparkling dresses and miniskirts that embody Larsson’s “never-ending summer” aesthetic.
“I can create new stuff from scratch with smaller designers, things that you’re just not seeing on the runway, and things that are going to be only for Zara,” Ospina says.
After all, putting someone else on is a way of paying it forward.
“It’s a moment to be able to showcase someone’s talent on a larger scale,” Webb adds. “As celebrity stylists, we have an obligation to younger designers, to propel those voices into mainstream success, because that helps fashion evolve.”
