After the creative director Daniel Lee celebrated Burberry’s 170th birthday in London, the Spring/Summer 2027 spotlight shifted to Milan Fashion Week. Before Marie Claire editors could process the celebrity looks at McQueen, Simone Rocha, and Burberry, celebrities dashed to Italy for the third installment of Fashion Month, which runs from September 22 to the 28.
On Day 1, Prada set high style standards for fellow luxury fashion houses like Fendi, Roberto Cavalli, and Emporio Armani—and we’re not just talking about the runway show. While statement skirts fluttered down the catwalk, everyone from Alexa Chung to Uma Thurman followed Miuccia Prada and Raf Simons’s lead by modeling standout midis in the front row.
Once the sun started to set over the Galleria Vittorio Emanuele II, an entirely new guest list of VIPs attended Vogue World. Jennifer Lopez—whose peekaboo bra announced her arrival the night before—turned heads in a tea-length little black dress from Dolce & Gabbana’s Alta Moda show. Vogue’s fifth annual fashion show also welcomed Ciara, Pamela Anderson, and Jordyn Woods. The A-listers honored the black-tie dress code in different ways: While Anderson opted for a metallic gold Ferragamo gown, Woods protested the “no white after Labor Day” rule in a creamy Stéphane Rolland number.
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Milan Fashion Week is just getting started: Gucci, Alberta Ferretti, and Marni have yet to take center stage, meaning some of the best celebrity looks remain in the queue. Before applauding Marie Claire‘s favorites below, bookmark this page to stay up to date on all the street style updates.
Jennifer Lopez at ‘Vogue’ World 2026: Milano
Jennifer Lopez at Milan Fashion Week.
(Image credit: Getty Images)
Before Jennifer Lopez delivered a surprise dance performance at Vogue World, she posed for the paparazzi in a strapless Dolce & Gabbana dress. Glossy embroidery made the tea-length dress shine, but all eyes went to the aquamarine-looking pendant on her Dolce & Gabbana necklace.
Ciara at ‘Vogue’ World 2026: Milano
Ciara at Milan Fashion Week.
(Image credit: Getty Images)
Being pregnant with her fifth child didn’t stop Ciara from returning to Vogue World. (The pop star RSVP’d “yes” in 2024, too.) This time, she kept it classic in a little black dress, platform stilettos, and a gold necklace stack.
Pamela Anderson at ‘Vogue’ World 2026: Milano
Pamela Anderson at Milan Fashion Week.
(Image credit: Getty Images)
Pamela Anderson stepped outside of her less-is-more comfort zone for Vogue World, arriving in a bubble-hem, metallic gold gown from Ferragamo’s Fall 2026 show.
Jordyn Woods at ‘Vogue’ World 2026: Milano
Jordyn Woods at Milan Fashion Week.
(Image credit: Getty Images)
For her first Milan Fashion Week sighting since 2023, Jordyn Woods sourced Stéphane Rolland for a structural, shoulder-padded turtleneck and a skintight, ankle-sweeping skirt. The Woods by Jordyn founder earned extra style points for shade-matching her pointy pumps to her waistband’s gold-dyed strands.
Heidi Klum at ‘Vogue’ World 2026: Milano
Heidi Klum at Milan Fashion Week.
(Image credit: Getty Images)
Lopez limited her look’s sheerness to mesh opera gloves, but Heidi Klum held down the naked fashion fort in a lacy, thong-revealing dress by Celia Kritharioti. If the Greek designer’s name sounds familiar, that’s because, last July, Lopez watched the designer’s Paris Couture Week show in (what else?) a semi-sheer slip dress.
Maya Hawke at Prada
Maya Hawke at Milan Fashion Week.
(Image credit: Getty Images)
Meanwhile, at Prada, Maya Hawke proved summer’s Bermuda shorts trend has major fall potential in a cool-blue pair, a navy V-neck sweater, and razor-sharp slingback pumps, which brought NYFW’s purple color trend to Milan.
Naomi Watts at Prada
Naomi Watts at Milan Fashion Week.
(Image credit: Getty Images)
Perhaps anticipating the statement skirt takeover on Prada’s runway, Naomi Watts paired a silky black blouse with a pleated aqua midi. Zoom in to appreciate the skirt’s bridge illustration, which added even more dimension to the already bold design.
Nara Smith at Prada
Nara Smith at Milan Fashion Week.
(Image credit: Getty Images)
Among Prada’s sea of unconventional skirts, bralettes and peekaboo lingerie played a part in the Spring 2027 show. Nara Smith brought the trend onto the street style scene, wearing a white bra top with a black pencil skirt and a matching east-west bag.
Uma Thurman at Prada
Uma Thurman at Milan Fashion Week.
(Image credit: Getty Images)
NYFW’s red color trend resurfaced in Milan, thanks to Uma Thurman. The actor’s short-sleeve sweater featured the same crimson shade seen at Michael Kors and Carolina Herrera. She tucked the top into a pleated camel-colored skirt.
Emilia Clarke at Prada
Emilia Clarke at Milan Fashion Week.
(Image credit: Getty Images)
Leave it to Emilia Clarke to elevate a zip-up sweatshirt at Prada’s spring show. The Game of Thrones star’s loungewear looked surprisingly luxe with an office-friendly pencil skirt and day-to-night pumps.
Gabrielle Union and Dwyane Wade at Prada
Gabrielle Union at Milan Fashion Week.
(Image credit: Getty Images)
Just by wrapping a thick headband around her hair, Gabrielle Union gave her all-black look—complete with a belted pea coat and peekaboo LBD—a Fashion Week-worthy twist.
Alexa Chung at Prada
Alexa Chung at Milan Fashion Week.
(Image credit: Getty Images)
This Fashion Month alone, Alexa Chung has been to NYC, London, and now Milan. Following an appearance at Burberry, the model’s style series continued at Prada, where she buttoned a tomato-red cardigan over a sequin midi skirt. She even revived spring’s little pouch trend, which Prada endorsed early in the year.
