Hilary Duff and Shailene Woodley Lead Front-Row Glamour at Fendi in Milan as Duff Signals Return to Music

Milan Fashion Week got a star-heavy moment on Wednesday as Hilary Duff and Shailene Woodley led the front row at Fendi’s Spring/Summer 2026 show, a centerpiece of the Italian label’s Milan outing. The star power underscored a presentation that blended bold styling with the label’s latest designs, drawing a who’s who of entertainment figures to the front row.

Duff, 37, arrived in a striking red colour-block blouse paired with a turquoise satin skirt. She finished the look with pink peep-toe heels and a vibrant hot-pink basket-style bag, projecting a fearless palette that matched the event’s high-gloss mood. Woodley, 33, chose a more restrained yet daring silhouette in a brown velvet fishtail midi dress accented by a delicate lace bodice, complemented by gold statement earrings and a burgundy handbag.

In addition to Duff and Woodley, the guest list included Naomi Watts in a stylish grey suit, Isabela Merced in pink, Ryan Destiny in a turquoise suit and fur jacket, and Ren Meguro in a leather-clad look, among others. The gathering came just weeks after Duff signaled a major shift in her career, announcing a move into music with Atlantic Records and the launch of a docuseries about her long-awaited return to song.

Duff shared a trio of candid studio photos with her husband, Matthew Koma, a singer-songwriter and record producer who appears to be contributing to the production side of her new musical project. Her caption played coy about the timing, writing “new music ... or something” alongside disco-ball and cherry emoji icons, signaling an imminent artistic comeback without detailing a timeline for releases.

The project details remain under wraps, but industry outlets reported that the docuseries will be directed and executive produced by Sam Wrench and will chronicle Duff’s complex life as a mother, actress, musician and multi-hyphenate as she navigates balancing a family with live rehearsals and an onstage return after more than a decade away from the spotlight.

Duff’s move into music follows a long period focused on acting. Her last studio album, Metamorphosis, released in 2003, is commemorating its 22nd anniversary this year, a milestone Duff acknowledged in a recent social post featuring throwback photos and reminisces about writing and performing as a teenager. She previously released a 2020 cover version of Third Eye Blind’s “Never Let You Go” with RAC and Koma, marking a more recent foray into recording before the current push toward new material.

The Milan appearance, paired with the music-news momentum, signals Duff’s broader career strategy: maintain her strong acting presence while pursuing a renewed musical path and a documentary project that offers fans a closer, candid look at her life and aspirations. The upcoming music release date and the docuseries premiere have not been announced, but the collaboration with a major record label and the involvement of a noted director suggest the project could reach a broad audience when ready.

Duff is a mother to Luca Cruz, 13, from her marriage to Mike Comrie, and to daughters Banks Violet, 6, Mae James, 4, and Townes Meadow, 1, with Matthew Koma. She has been married to Koma since late 2019, and the couple has increasingly been linked to Duff’s artistic revival, including glimpses of studio work and production involvement in her upcoming material. The docuseries is described as following the ups, downs and everything in between as she balances family life with touring, rehearsals, and the emotional expectation of performing on stage again after a long hiatus.

As Fendi rolled out its latest collection on the Milan runways, Duff and Woodley’s presence underscored the design house’s appeal to a new generation of multi-hyphenate stars who blend fashion with music, film and streaming-era storytelling. The show’s reception aligned with a broader trend in Milan Fashion Week, where style and entertainment intersect to spotlight cross-disciplinary talents and high-profile collaborations.