Major Fashion And Culture Moments From Vogue World Milan

Major Fashion And Culture Moments From Vogue World Milan
Source: Getty // Major Fashion And Culture Moments From Vogue World Milan

Vogue World Milano kicked off Milan Fashion Week on September 22 as fashion month continues. The fifth iteration of the legacy fashion magazine’s now-signature event took over the Galleria Vittorio Emanuele II, celebrating Italian fashion through archival pieces, custom designs and current collections.

The designer lineup was fire, the celebrity and fashion-insider sightings were as exciting as we’d expect, and fashion history was everywhere. Versace, Prada, Armani, Gucci, Valentino, Fendi, Bottega Veneta and Dolce & Gabbana were among the major houses represented.

The pictures from the event alone have us swooning!

Fashion moments happened on the catwalk, in the audience and even during rehearsal. Cardi B walked the runway. Alicia Keys helped close the show. Naomi Osaka, Taraji P. Henson and Jordyn Woods were among many celebs bringing style and attitude to Milan. And other Black Hollywood favs like Ciara, Gabrielle Union, Dwyane Wade, Naomi Campbell and Alton Mason were also spotted during the event.

Scroll for some of our favorite fashion moments.

Thanks To Donatella Versace, Cardi B Brings A Little Bronx Attitude To Milan

Vogue World: Milano 2026 - Runway / Show
Source: Arnold Jerocki / Getty

Cardi B made rehearsal part of her Vogue World moment before the show even started. Vogue shared footage of Cardi practicing her walk in a fitted blush-pink look with the caption: “Cardi B turned Vogue World Milano rehearsal into the main event.”

For the show, Cardi went into the Versace archives. She wore a body-skimming Spring 2018 Versace dress covered in pop-art interpretations of vintage Vogue covers. Donatella Versace created the collection in honor of Gianni Versace, revisiting prints tied to his work. Cardi finished the look with Tiffany & Co. bone cuffs, Versace shoes, purple nails and full curls. The print was bold and colorful, and the silhouette was made for Cardi’s curvy bawdy. With this Donatella look, the femcee brought a little Bronx attitude to Milano.

Naomi Osaka Took Her Fashion Prowess Across The Pond

Naomi Osaka has been serving fashion all month long. The tennis champion turned the U.S. Open into a peek inside her fashion closet and sports inspirations as she gave us look after look at practice, on game day and after. Naomi took this fashion prowess to Milan with a completely different energy.

For Vogue World, she wore Roberto Cavalli Fall/Winter 2026/27 Look 44, pairing a sheer black lace top with a voluminous skirt covered in layers of feathery texture. The look was ethereal yet fierce, dark and feminine at the same time. Black strappy heels, a small black bag and oversized rectangular gold earrings finished the fit.

Makeup artist Sheika Daley gave Naomi deep, glowy skin, smoky eyes and a soft nude lip. Hairstylist Aminata Kamara pulled her hair into a sleek, long braided ponytail that showed off Naomi’s gorgeous cheekbones and put even more attention on her melanin glow. Against the sheer black lace and dramatic texture, the beauty look added another layer of femininity to the fit.

Jordyn Woods Gave Us Shape, Structure And Gold

Vogue World: Milano 2026 - Arrivals
Source: Daniele Venturelli / Getty

Fresh off front-row appearances at NYFW and her gorgeous wedding to Karl-Anthony Towns, Jordyn Woods added to the star power in Milan. She looked grown, sophisticated and oh-so chic in Stéphane Rolland. Her Spring/Summer 2025 look featured strong shoulders, a sharply defined waist and a fitted column skirt. Her curves were curving, OK?!

Long gold fringe dropped from the center of the bodice, adding movement against the clean white silhouette. Jordyn paired the look with metallic gold pumps, a gold clutch and statement earrings. The sharp shoulders, snatched waist and gold details gave us a grown-woman fashion moment from Jordyn.

Taraji P. Henson Came Through In A Snatched Corset

Vogue World: Milano 2026 - Arrivals
Source: Daniele Venturelli / Getty

Taraji P. Henson gave us one of the sexier black looks of the night. Styled by Kollin Carter, Taraji wore a Yara Shoemaker gown with a strapless satin corset, lace cups and sculpted hips that hugged and celebrated her curves.

The sheer skirt brought lace, embroidery and sparkle, while drop earrings, stacked rings and a diamond bracelet added even more shine. Taraji wore her short hair slicked close to her head with dramatic lashes and a nude lip. From the corset to the sheer detailing, Taraji reminded us why she and Kollin continue to be one of our favorite fashion pairings.

Alicia Keys Closed Vogue World Looking Like A Werk Of Art

Vogue World: Milano 2026 - Runway / Show
Source: Daniele Venturelli / Getty

Alicia Keys helped close Vogue World with Donna Summer’s “I Feel Love,” performing at the piano while models dressed in white surrounded her.

Alicia wore a custom Francesco Risso creation made with satin, chiffon, georgette and crêpe de Chine. Artist Flaminia Veronesi hand-painted the massive train with blues, creams, oranges and darker brushstrokes spread across the fabric. Alicia described the night as one where “fashion became art,” and she looked like a werk of art herself.

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