Hilary Duff and Shailene Woodley Lead Front-Row Glamour at Fendi Show in Milan

Milan Fashion Week opened with a splash of glamour at Fendi’s show, where Hilary Duff and Shailene Woodley led the front row during the brand’s Spring/Summer 2026 presentation. The two actresses sat among a star-studded guest list that included Naomi Watts, Isabela Merced, Ryan Destiny, and Ren Meguro, all eyes fixed on the mood and silhouette that the house teased on the catwalk. Duff arrived in a bold red color-block blouse paired with a turquoise satin skirt, finishing the look with pink peep-toe heels and a hot-pink basket bag. Woodley followed with a brown velvet fishtail midi dress featuring a delicate lace bodice, complemented by gold statement earrings and a burgundy handbag. The pairing underscored the current season’s mix of color-block drama and tactile textures that Milan’s fashion crowd has come to expect from Fendi.

The appearance came on the heels of a flurry of personal-news headlines for Duff, who has been navigating a major career shift in real time. In the weeks leading up to the show, the 37-year-old former Disney star announced that she had signed with Atlantic Records and is developing a docuseries that will chart her long-awaited return to music. Duff posted three candid studio photos in which she records alongside her husband, Matthew Koma, a singer-songwriter and producer, signaling a new chapter after years focused on acting and family life. Her last studio album, Breathe In. Breathe Out., was released in 2015, and fans welcomed the prospect of new music after a decade away from the music stage.

Duff’s social post accompanying the studio images suggested she was exploring “new music … or something,” pairing the update with emojis of a disco ball, sparkles, and cherries. While specifics about the music release date or a formal premiere for the docuseries remain under wraps, multiple outlets reported that the project will offer an inside look at her balancing act as a mother of four, a performer, and a creator stepping back into the recording studio after a prolonged hiatus. The docuseries is described by Variety as being directed and executive produced by Sam Wrench, and it will follow Duff as she prepares to perform on stage for the first time in more than a decade.

Duff’s return to music also comes as she has gradually shifted back into acting projects. Her Instagram posts in recent years have highlighted her ongoing work in television, including roles on Younger and How I Met Your Father, while the Lizzie McGuire reboot, which was in development for Disney, was ultimately shelved before it could premiere. Her last music release prior to the current project was a 2020 collaboration—covering Third Eye Blind’s Never Let You Go with RAC and Koma. The renewed focus on music accompanies a broader conversation about how the multi-haceted star intends to balance family life with touring and live performances.

Duff is a mother to Luca Cruz, 13, from her marriage to Mike Comrie, and shares daughters Banks Violet, Mae James, and Townes Meadow with Matthew Koma. The couple has been married since late 2019, and Koma has been openly involved in Duff’s new music endeavors, including production contributions visible in her social media posts. In addition to her personal life, Duff’s professional trajectory has included a steady return to screen acting, with fans watching closely for how her music might intersect with future performances, live shows, and any forthcoming documentary material.

The Fendi event highlighted how fashion can intersect with an artist’s evolving career, serving as a high-profile platform for announcements, teases, and collaborations alike. While the exact timing of Duff’s new music rollout and the docuseries premiere remains to be announced, the Milan appearance underscored the momentum behind her reemergence in the entertainment landscape. For Shailene Woodley, the moment reinforced her ongoing status as a fashion-forward fixture in front-row spaces, adding to a year that has seen her balancing film projects with high-profile style moments that resonate across culture and entertainment audiences. Other guests at the show, including Naomi Watts in a grey suit, Isabela Merced in pink, Ryan Destiny in a turquoise suit and fur jacket, and Ren Meguro in all-leather, contributed to a mood many described as elegant yet fearless, a hallmark of Fendi’s design philosophy for the season.

As Milan Fashion Week continues, industry observers will watch not only for the collection’s reception but also for how Duff and Woodley’s public-facing projects evolve in tandem with their appearances on runways and at shows. The pairing of fashion-forward front-row moments with announced music and documentary ambitions illustrates how the modern celebrity landscape often blends multiple creative disciplines in a single news cycle. With the docuseries in development and Atlantic Records now in the fold, Duff’s fans may expect a multi-pronged return that could bring new dimensions to her public narrative—from stage to screen and beyond.