The Best Celebrity Looks Are Bringing the Drama to Milan Fashion Week
Cardi B and Naomi Watts are making the city their runway.
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 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.
Fast forward to Sept. 25 and the street style spotlight shifted to Gucci's star-studded guest list. While Camila Morrone and Keke Palmer answered the spring runway show's call for statement coats, Naomi Watts's fitted satin suit added a fresh new shade to her growing color palette: magenta. That same day, Tod's welcomed a slew of neutral supporters, including Katie Holmes in a white T-shirt, a khaki trench coat, and the celebrity-beloved belt bag trend.
Milan Fashion Week is not over yet: Bottega Veneta and Giorgio Armani 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.
Katie Holmes at Tod's
Katie Holmes at Milan Fashion Week.
Migrating her neutrals series from New York City to Milan, Katie Holmes attended the Tod's show in a white T-shirt, a classic trench coat, and ivory trousers. The actor shade-matched her black leather loafers to the Italian label's T Signature Small Handbag, personalized with her initials as charms on the belt worn for decoration.
Diane Kruger at Tod's
Diane Kruger at Milan Fashion Week.
Diane Kruger brought the same It bag to Tod's spring runway show, except in a slightly smaller size. The personalization element separated the silhouette from other popular belted bags, including the Prada Bonnie and the Miu Miu Aventure.
Camila Morrone at Gucci
Camila Morrone at Milan Fashion Week.
Channeling the energy of an Italian donna, Camila Morrone gave her lace-trimmed little black dress a more-is-more twist. The Daisy Jones and the Six star layered on a cream-colored fur coat, courtesy of Gucci's Fall 2026 show (Demna's debut).
Naomi Watts at Gucci
Naomi Watts at Milan Fashion Week.
As soon as Naomi Watts slipped on her satin magenta suit, the actor went full movie-star mode for Gucci. She also went shirtless under the fitted blazer, accessorizing only with shield sunglasses and a classic Gucci horsebit bag.
Keke Palmer at Gucci
Keke Palmer at Milan Fashion Week.
Keke Palmer picked the perfect power blazer for the Gucci show: a double-breasted pinstripe design with chocolate brown fur covering each sleeve. To finish her front-row look, the actor click-clacked into the venue in the high-vamp heels trend.
Bianca Jagger at Gucci
Bianca Jagger at Milan Fashion Week.
Bianca Jagger made her Gucci debut in an all-white skirt suit that resembled her famous 1971 wedding look, which still influences brides today (including, most recently, Dua Lipa).
Olandria Carthen at Blumarine
Olandria Carthen at Milan Fashion Week.
Serving Cruella de Vil fabulousness outside the Blumarine show, Olandria Carthen paired a lacy, lingerie-looking bodysuit with a black-and-white furry stole that stretched far beyond the Love Island star's tights and pointy pumps.
Cardi B at Roberto Cavalli
Cardi B at Milan Fashion Week.
Cardi B brought the drama to Roberto Cavalli's front row: The rapper wore the most fabulous fur-trimmed coat, which revealed a peekaboo corset, a plunge neckline, and cool-toned animal prints. Don't miss the leopard-spotted stilettos that emerged from beneath the robe's sidewalk-sweeping train.
Sloane Stephens at Roberto Cavalli
Sloane Stephens at Milan Fashion Week.
Not only did the tennis player serve a style Grand Slam outside Roberto Cavalli, but Sloane Stephens endorsed an unconventional color combination for fall: electric pink and purple (which is already having a Milan Fashion Week moment on its own).
Adria Arjona at Max Mara
Adria Arjona at Milan Fashion Week.
By layering the peekaboo bra trend under her espresso blazer, Adria Arjona demonstrated her Max Mara outfit's day-to-night potential.
Kate Mara at Max Mara
Kate Mara at Milan Fashion Week.
Early in the month, Kate Mara arrived at the 2026 Venice Film Festival in a full Max Mara Resort 2027 outfit. For the brand's Milan Fashion Week show, she sourced the same collection for a belted coat, matching mini skirt, and the (sold-out) Max Mara Whitney Bag.
Leighton Meester at Max Mara
Leighton Meester at Milan Fashion Week.
Leighton Meester reunited with her Gossip Girl co-star, Kelly Rutherford, at the Max Mara show. Serena van der Woodsen would've adored the green sequins on her BFF's Resort 2027 skirt.
Kelly Rutherford at Max Mara
Kelly Rutherford at Milan Fashion Week.
If Kelly Rutherford's Gossip Girl character, Lily van der Woodsen, were to test fall's funnel-neck jacket trend, she'd choose this black Max Mara coat. The beige T-strap shoes added a touch of softness.
Madelyn Cline at Etro
Madelyn Cline at Milan Fashion Week.
Hours after Madelyn Cline was spotted wearing Adidas Samba Jane sneakers and a vintage Chanel bag in Milan, she reappeared at the Etro show. But not before slipping into a paisley-printed, sheer feather-trimmed dress.
Cardi B at Off-White
Cardi B at Milan Fashion Week.
Surrounded by the glitz and glamour of Milan Fashion Week, Cardi B pulled a storied Fashion Month staple out of her luggage: a sleek little black dress for the Off-White show.
Jennifer Lopez at 'Vogue' World 2026: Milano
Jennifer Lopez at Milan Fashion Week.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
