Hollywood’s Best Dressed Men: 10 Style Icons Who Always Steal the Show

Photo: Tyler Mitchell | Vogue

From red carpets to front rows, Hollywood's leading men are no longer just relying on classic tuxedos and tailored suits. These days, the most stylish gents are pushing the envelope with daring silhouettes, bold prints, and signature flair that turns every appearance into a fashion moment. Whether it’s luxury streetwear, high fashion or a nostalgic nod to retro cool, these ten men know exactly how to wear the clothes and not let the clothes wear them. They're not just wearing trends; they're creating them. Each one brings a distinctive energy that makes the fashion world take notice.

1. Shaboozey: The Cowboy with Couture Cred

Shaboozey brings Western swagger to the red carpet with a high fashion twist. Known for blending Americana with streetwear, he’s the kind of artist who can wear cowboy boots and a ten-gallon hat with a designer trench coat and make it look effortless. His style nods to his music, which fuses country and hip-hop, creating a refreshing aesthetic that feels both nostalgic and new. He’s not afraid to embrace his roots while giving them a modern edge. With each look, he reminds us that individuality is the ultimate statement piece.

2. A$AP Rocky: The Fashion Killa

There’s a reason why A$AP Rocky is beloved by both rap fans and fashion editors. The Harlem-born rapper is fearless in his style choices, often mixing high fashion with vintage finds, streetwear staples, and unexpected textures. Whether he’s in a silk headscarf or a quilted skirt, Rocky turns looks that are provocative, polished, and always ahead of the curve. He collaborates with designers just as easily as he headlines festivals. His fashion sense is rooted in confidence, making every outfit a moment of cultural commentary.

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3. Jason Momoa: Bohemian Brawn

Jason Momoa is proof that masculinity and fashion aren’t mutually exclusive. He’s become synonymous with flowy pink suits, layered necklaces, and well-loved boots. With a wardrobe that leans into earthy tones, eclectic fabrics, and boho accessories, Momoa’s style feels like a desert rock star who just stepped out of an art gallery and we love him for it. He wears his heritage proudly, often incorporating Native Hawaiian and Polynesian elements. His approach to fashion is laid-back yet deeply intentional, never performative.

4. Bad Bunny: Genderless Glamour

Bad Bunny is revolutionising menswear with fearless gender-fluid fashion. Whether he’s donning latex bodysuits, painted nails, or skirts on stage and on the red carpet, the Puerto Rican superstar is making a powerful statement: wear what you want. His fashion sense is bold, theatrical, and gloriously unbothered by norms. This is what makes him a true trailblazer. He brings a sense of freedom to every look, blurring lines between genres and genders. Bad Bunny’s style is as unpredictable and magnetic as his music.

5. Pharrell Williams: The Visionary

Pharrell is more than a fashion icon, he’s a creative force shaping the industry. From oversized hats to Chanel pearls and now as Louis Vuitton’s menswear creative director, his wardrobe is a masterclass in avant-garde meets street luxe. He’s never afraid of colour, texture or whimsy, and that sartorial bravery has made him one of the most influential dressers of our time. Pharrell’s looks often challenge traditional fashion hierarchies, blending luxury with subculture. Every appearance feels like a curated exhibit of the future of menswear.

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6. Jacob Elordi: The Modern Gentleman

Jacob Elordi has become the poster boy for elegant minimalism. Often dressed in clean silhouettes, crisp tailoring, and muted palettes, he brings a quiet luxury to the red carpet. Whether in classic Saint Laurent or vintage Prada, he makes old-school movie star glamour feel contemporary. His style feels intentional and well-researched, always polished but never too try-hard. Jacob’s looks resonate with fashion lovers who favour timeless pieces over trends.

7. Bruno Mars: Retro Royalty

With a love for vintage Versace, silk shirts, and gold chains, Bruno Mars channels a '70s lounge lizard vibe—only sharper and shinier. His style is flamboyant, funky, and dripping in throwback cool. Whether performing or posing, he serves full character, proving that fashion is also about performance and panache. Bruno’s wardrobe is built around a persona that’s equal parts charm and swagger. He reminds us that confidence is the real key to pulling off bold fashion.

8. Colman Domingo: The Sartorial Storyteller

Colman Domingo brings elegance and boldness in equal measure. He’s mastered the art of colour and tailoring. Think fuchsia suits, brocade jackets, and eye-catching lapels. Domingo’s red carpet looks often tell a story, blending old Hollywood charm with modern silhouettes and subtle references to Black excellence and queer identity. His fashion reflects his deep understanding of culture, history, and presence. Colman dresses with purpose, making every outfit a meaningful statement.

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9. Daniel Craig: The Timeless Rebel

As James Bond, Daniel Craig wore a suit like it was second skin and off screen, he hasn’t missed a beat. His personal style blends classic British tailoring with just enough ruggedness to keep it interesting. Think bespoke suits with a rebellious twist: rumpled linen, unexpected colours, or a cheeky accessory. He’s not flashy, but he knows how to stand out with quiet authority. Daniel’s style proves that refinement and rebellion can exist in the same look.

10. Lewis Hamilton: The High-Speed Fashionista

Lewis Hamilton isn’t just fast on the track, he’s lightning quick to clock fashion trends, too. The Formula 1 champ is known for his bold streetwear, designer collaborations, and gender-inclusive looks. From pastel suiting to oversized puffer jackets, his style is eclectic, expressive, and refreshingly fearless. He uses his platform to champion sustainability and inclusivity in fashion. Hamilton's wardrobe choices reflect his personal evolution and global influence.

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These ten men remind us that fashion is a playground, not a rulebook. Whether through tailoring, texture, or total transformation, they continue to redefine what it means to be stylish in Hollywood. Each with his own flavour, these icons aren’t just best dressed—they’re shaping the future of menswear, one outfit at a time.

They’ve proven that great style is about more than just appearance—it’s about self-expression, identity, and storytelling. In a world obsessed with trends, these men are carving out timeless legacies through their clothes.