In February, at Veronica Leoni’s debut show for Calvin Klein in New York, one bold menswear look stood out. Stylist Julie Ragolia immediately thought of actor Pedro Pascal when she saw a model wearing a sleeveless knit with deep-cut armholes paired with simple black trousers. Knowing Pascal’s fearless approach to fashion, she reserved the outfit. When he wore it on the Cannes Film Festival red carpet, the look went viral. Headlines declared that “Cannes Is Warm but Blacked-Out Calvin Klein is Hot,” and the internet lit up with praise for Pascal’s daring style.
Cannes 2025 offered a masterclass in men’s fashion as a form of bold self-expression. Alexander Skarsgård strutted in thigh-high boots, Jeremy Strong wore a full pink corduroy look, and A$AP Rocky donned a white Miu Miu suit complete with sparkling jewelry. These daring choices reflect a growing trend: male celebrities are enjoying fashion like never before, breaking traditional style rules and embracing creativity.
This wave of expressive menswear isn’t the work of a single stylist but the result of dynamic collaborations between talented stylists and celebrities with strong personal style. For example, Colman Domingo and stylist duo Wayman Bannerman and Micah McDonald have consistently delivered standout red carpet looks, such as a hot pink Versace suit at the 2021 Oscars. Domingo’s 2025 Met Gala appearance as cochair featured two bold Valentino ensembles, including a striking blue cape and a sharp black-and-white suit.
Bannerman and McDonald credit their success with Domingo to a shared willingness to take risks. “He has been one of our greatest collaborators over the years because he is always open to play and have fun,” they explain. Domingo’s style also thrives under the creative vision of Valentino’s Alessandro Michele, known for romantic touches like silk pajamas, classic footwear, and vintage-style scarves.
Ragolia, meanwhile, finds inspiration in designers like Miuccia Prada, Anthony Vaccarello of Saint Laurent, and Pierpaolo Piccioli (formerly of Valentino and now at Balenciaga), as well as emerging labels such as 3.Paradis, Aubero, and Kartik Research. “Men’s fashion is in one of the most dynamic states ever,” she says. “Menswear has long understood consistency and form, and that reliability is now driving how women dress too.”
Daniel Todd, buying director at Mr. Porter, echoes this sentiment. He sees modern menswear icons like Timothée Chalamet, A$AP Rocky, and Domingo as symbols of a wider fashion shift. “Brands like Bottega Veneta, Loewe, and Lemaire are reinterpreting classic menswear through relaxed silhouettes, luxurious fabrics, and thoughtful detailing,” Todd says. These fresh takes on tailoring allow men to explore both structure and fluidity in their clothing.
This evolution in menswear goes beyond aesthetics—it’s reshaping social expectations. “The appetite for self-expression has grown,” Todd adds. “There’s more freedom and more options than ever for men to show individuality through fashion.” As the boundary between formal and casual styles continues to blur, designers are responding with pieces that blend proportion, texture, and color in new, innovative ways.
The most powerful fashion statements often mix elements that were once considered opposites—masculine and feminine, formal and relaxed. Ragolia’s outfit for LaKeith Stanfield at the 2021 Academy Awards, a Saint Laurent jumpsuit based on a womenswear design, is one such example. Bannerman and McDonald also routinely incorporate traditionally feminine accessories—like hats and gloves—from womenswear lines into Domingo’s outfits. Even though his Valentino pieces are labeled menswear, they often include soft, romantic details.
This isn’t the first time men have experimented with womenswear, but celebrities like Harry Styles helped normalize the trend in recent years. Styles, with the help of stylist Harry Lambert, wore feminine blouses, dresses, and accessories like feather boas and beaded necklaces. Chalamet recently turned heads by accessorizing with women’s Chanel bags, sparking excitement across social media. “Anything goes now in menswear!” Bannerman and McDonald say. “Men can have just as much fun on the red carpet as women.”
But what really makes these fashion risks work is authenticity. “I don’t intentionally take risks, nor do I invite anyone to take risks for the sake of it,” Ragolia emphasizes. She points to Kristen Stewart—who famously protested Cannes’ dress code by walking barefoot—as an example of pure, genuine expression. Pedro Pascal echoes that authenticity, wearing T-shirts with powerful messages like “Protect the Dolls,” advocating for trans women, and “Adult Content,” a design by trans artist Pippa Garner used to raise money for trans rights.
“I support my clients in expressing who they are,” Ragolia says. “Playfulness is great, but they need to feel like themselves. We’re a team.” This teamwork results in fashion moments that resonate deeply with fans. For instance, Pascal’s rise as a style icon didn’t start with over-the-top outfits but with something simple: sweaters. A silver cardigan, a knit draped around his shoulders, or a regular cardigan worn with confidence sparked widespread attention. “That was exciting,” Ragolia recalls, “because everyone has a sweater in their closet. There were no tricks—just a fresh take on the everyday.”
In an era where fashion is more inclusive and diverse than ever, menswear has emerged as a powerful space for creativity, activism, and joy. The modern man is no longer bound by tradition. Whether it’s a dramatic cape or a simple knit, what matters most is how the clothing makes him feel—and that, more than anything, is what’s truly fashionable.
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