The Best and Worst Dressed Stars at Vogue World: Milano 2026 — Heidi Klum, Jennifer Lopez, Pamela Anderson & More — Photos

Milan Fashion Week delivered no shortage of contrasts, as celebrities stepped out in everything from polished gowns and sharp tailoring to sheer, skin-baring designs.

Some embraced classic glamour, while others experimented with metallic fabrics, dramatic proportions, and unexpected styling. Several of those choices also divided opinion online, drawing both enthusiastic praise and pointed criticism from netizens.

Here is a closer look at the fashion moments that stood out - and what social media users had to say about some of the most discussed looks.

A Celebration of Italian Fashion

Much of the action unfolded at Vogue World 2026: Milan, staged inside the Galleria Vittorio Emanuele II. According to Vogue, the fifth edition celebrated Italy's century-spanning contributions to fashion while examining the value of human craftsmanship in an increasingly technology-driven era.

The production drew inspiration from different periods of Italian history, from the ornate craftsmanship of the Renaissance to the transformations of the Industrial Revolution. It also looked toward the future, considering how Italy's heritage fashion houses could influence fashion's next chapter.

The spectacle extended beyond the traditional runway. Celebrity guests watched from the front row, while some surprise participants also appeared in the show itself.

Pamela Anderson

Pamela Anderson went all-in on gold at Vogue World: Milano 2026 on Sept. 22. Her metallic gown favored volume over a body-hugging silhouette, falling loosely through the body before gathering into an exaggerated, balloon-like skirt.

The accessories stayed firmly within the same color story. Anderson layered on chunky gold jewelry, while a structured black handbag provided a sharp contrast. Her platinum-blond hair, sculpted into vintage-style curls, brought an Old Hollywood touch to one of the more unconventional silhouettes of the occasion.

The Milan appearance also marks Anderson's latest experiment with makeup after she became known for embracing a pared-back beauty routine. In a TikTok "Get Ready With Me" video, Anderson explained that she started with fresh-looking skin using products from her Sonsie brand before Pat McGrath's team stepped in.

"I'm convinced that skin just looks better raw," she said. For the finishing touch, she wanted "a little bit of Cleopatra inspiration" around the eyes to complement her Ferragamo outfit.

Anderson's move away from heavy makeup has a deeply personal history. The "Baywatch" star told Elle in 2023 that she reconsidered her signature glam after her longtime makeup artist, Alexis Vogel, died of breast cancer.

"She was the best," Anderson said of Vogel. Going without makeup later became "freeing, and fun" for Anderson, who also called the change "a little rebellious" as elaborate beauty looks remained popular.

The shift also reflected Anderson's changing perspective on aging and her appearance. She told the magazine that looking in the mirror had become part of "a journey," adding, "I feel good. I'm in a good place."

That change has not stopped her from occasionally revisiting her past.

Anderson brought back elements of her '90s beauty aesthetic for a Smashbox Cosmetics campaign in 2024. In an Instagram post about the collaboration, she called the project a "fun 'wink to the past'" while making clear that the high-glam style was no longer her usual aesthetic.

"It was very flash back then… but those were the days…Rock'n roll… bedazzled, shiny everything… silver, black and red… oh my ha," she added.

She also offered a broader view of beauty and cosmetics: "Make up is a fun extension of who we are, but it isn't all we are."

Donatella Versace

Donatella Versace brought silver and leather together for one of the edgier combinations in Milan. The Italian designer paired a gleaming sleeveless top with a black leather miniskirt, while a statement belt added another flash of metallic hardware.

Towering black platform boots gave her outfit a rock 'n' roll edge, complemented by her signature straight platinum-blond hair. Beside her, fellow Italian designer Pierpaolo Piccioli echoed the leather theme with a black leather jacket, loose black trousers, white sneakers, and dark sunglasses.

While Versace went high-shine and fitted, Piccioli kept his look relaxed and understated, giving the pair two very different takes on black leather.

Ciara

Ciara gave the little black dress a dramatic new shape with a fitted mini that showed plenty of leg before dropping into a long, trailing panel on one side. The contrast between the abbreviated hem and floor-skimming fabric gave the otherwise streamlined dress its defining twist.

She added even more height with towering black platform stilettos, while an oversized gold charm necklace and stacked bracelets brought color and shine to the all-black look. Her voluminous waves completed the styling, balancing the dress's sleek, body-skimming silhouette.

Jason Momoa

Jason Momoa put his own spin on pale pink pinstripes, pairing the softly colored suit with a simple white top instead of a dress shirt and tie. The relaxed styling immediately took some of the formality out of the tailored two-piece.

He doubled down on that approach with tinted glasses, statement rings, and a slim crossbody bag. Brown slip-ons replaced traditional dress shoes, while his pulled-back hair and visible hand tattoos added to the laid-back contrast. Even in pastel tailoring, Momoa kept the look firmly within his easygoing style.

Uma Thurman and Daughter Maya Hawke

Uma Thurman and Maya Hawke approached mother-daughter dressing by not dressing alike at Prada's Spring/Summer 2027 womenswear show. Thurman leaned into warm shades with a vivid red knit top, pleated brown skirt, and sweeping chocolate-colored coat.

Hawke went cooler and more casual beside her. A dark V-neck sweater and powder-blue knee-length shorts formed the base of her outfit, while purple pointed pumps delivered an unexpected pop of color. Together, the contrasting looks put their individual styles on full display.

Matthew McConaughey's Wife, Camila Alves

Brazilian model Camila Alves went head-to-toe white in a wrap-style ensemble with a plunging V-neckline and a long, fluid silhouette. With no bold colors or heavy embellishment competing for attention, the draped shape of the outfit did most of the work.

She kept the styling similarly restrained with layered necklaces and neutral open-toe heels. Her long dark waves provided a sharp contrast against the crisp white fabric and completed the minimalist look.

Paul Walker's Daughter, Meadow Walker

Meadow Walker took a bolder approach with a brown two-piece tied together by black ribbon details. Her cropped top featured puffed sleeves, a plunging neckline, and a prominent bow at the center, leaving her midriff exposed.

The matching skirt carried the ribbon detailing down the front, while a multicolored jeweled necklace added an unexpected burst of color. With her hair slicked back, the dramatic neckline and decorative ties remained front and center.

Jennifer Lopez

Jennifer Lopez went for full-scale drama in a strapless black ball gown covered with dark floral embellishments.

The fitted corset-style bodice opened into a sweeping, voluminous skirt, while sheer opera gloves added another glamorous layer. The "Office Romance" star finished the look with diamond jewelry, including a necklace centered with a large green stone, and wore her highlighted hair in loose waves.

The gown became even more dramatic once Lopez moved. One photo captured her posing with her hands at her waist, while another showed her twirling during the showcase, sending the enormous skirt flying around her.

The reaction online, however, was not entirely about the dress. On Facebook, several users focused instead on Lopez's expression. One netizen said, "This woman always has her mouth open 🤣," poking fun at the expression she made for the cameras.

Another user shared, "You look beautiful, but it would sure be so much nicer with a smile!" while still complimenting her appearance. A commenter wrote, "That's a pretty dress, but she needs a new facial expression!"

On Instagram, the conversation swung much more heavily toward praise. One user wrote, "JLo [sic] finally dressing age appropriate." Another commenter declared, "JLO [sic] looks incredible 😍😍 wow 😮😮😮😮."

Someone else went even further, writing, "Another tough day for the J.Lo haters!! She looks absolutely spectacular-so glamorous and beautiful!!! I love it!!!❤️❤️👑👑"

Dakota Johnson

Dakota Johnson took the opposite approach, making barely there black the centerpiece of her look. She paired a tiny black minidress with a loose, cape-like layer that fell from her shoulders and extended well below the dress.

A sheer lace panel continued down to the "Fifty Shades of Grey" star's legs, while black peep-toe heels and a small handbag kept the entire outfit in the same dark palette.

Her signature bangs framed her face, and the simple styling left the plunging neckline and sheer fabric to do most of the talking. The result was one of the more revealing fashion gambles in the lineup.

On Facebook, the revealing outfit quickly split opinion. One netizen asked, "Where's Dakota Johnson's bra?? (That's her name right?)," reacting directly to the plunging neckline.

Another user shared a much broader criticism: "Women no longer dress, they undress, and the worst thing is that they do it at any age, there is no longer respect or modesty in the eyes of others."

Not everyone objected. A commenter wrote, "Her Face is the outfit. So beautiful." Someone else offered the blunt one-word verdict, "Vulgar."

On Instagram, one admirer kept the praise simple, writing, "Dakota looks Amazing🔥❤️🥵." Another commenter took aim at her appearance rather than the outfit, writing, "Face fillers should be banned."

Heidi Klum

Heidi Klum made sheer lace the entire point of her outfit. The model stepped out in a floor-length black lace dress that revealed a black bodysuit underneath, with floral patterns and vertical lace panels running from its high neckline to its hem. Black sunglasses, open-toe heels, and a clutch completed the monochrome styling.

The German supermodel gave photographers plenty of different angles. She waved while walking outside, smiled as she moved through the venue, and later turned over her shoulder for a closer look at the intricate lacework across the back.

On Facebook, the amount of skin on display became the main point of debate. One netizen wrote, "She's gone through menopause and has thickened in her mid section. Shes [sic] hanging on to her youth with everything she has. It's tough. I know."

Another user said, "Pls [sic] to know your age and what's appropriate." A third commenter took a softer approach, writing, "She is a beautiful, mature woman. She has a wonderful figure. But I feel she doesn't always need to be almost naked."

On Instagram, the response supplied a sharp contrast. One commenter wrote, "Best look she has had in a while 🔥. She looks fabulous ❤️." Another simply said, "That dress fits you perfectly."

Naomi Watts

Naomi Watts showed that Milan style did not have to mean maximum exposure.

In one daytime appearance, the "Mulholland Drive" star paired a short-sleeved black blouse with a vivid turquoise pleated midi skirt decorated with black sketch-like graphics. White cat-eye sunglasses, glossy black loafers, and a structured white Prada handbag made the color-blocked combination even more distinctive.

The British actress later switched directions completely. Watts stepped through the venue in a clean white midi dress with jeweled detailing along the neckline, silver strappy heels, and sparkling earrings. A black jacket draped over her shoulders supplied the only major dark contrast, turning the second outfit into a far more minimalist fashion statement.

Michelle Williams

Michelle Williams offered a quieter counterpoint to some of the week's most revealing outfits. The "Dawson's Creek" actress wore a fitted cream midi dress scattered with tiny pink-and-green flowers, with a slim belt defining the waist. Pointed black slingback heels and a small black handbag gave the delicate floral print a sharper finish.

Williams wore her blond hair slicked back with a center part and kept her jewelry minimal. Photographed from the front row and again outside, the simple silhouette remained the focus rather than oversized accessories or dramatic layers.

Milan Fashion Week offered everything from metallic volume and enormous ball gowns to sheer lace, plunging necklines, and quieter floral looks. The stars may have shared the same fashion spotlight, but their approaches to dressing for it were anything but alike.

The differences carried over to social media, where some netizens applauded the boldest looks while others questioned whether certain outfits revealed too much or missed the mark. If anything, the divided reactions showed just how subjective celebrity fashion can be.