From award shows and premieres to fashion's biggest night out, these unforgettable looks set a new standard for men's fashion.

Men's <a href="https://www.hommessingapore.com/culture/a-roundup-of-timothee-chalamet-best-style-fashion-moments" target="_blank" title="In Celebration of 'Wonka', Here are Timothee Chalamet&rsquo;s Best Style Moments" rel="noopener">red carpet outfits</a> are often overlooked or constrained by conventional standards that lean towards a more traditional and "masculine" aesthetic. However, behind the scenes of award shows, premieres, and the <a href="https://www.lofficielsingapore.com/fashion/met-gala-2024-theme-announcement-details-hosts-fashion-news" target="_blank" title="The 2024 Met Gala Theme Has Officially Been Announced" rel="noopener">Met Gala</a>, a revolution in men's fashion has been quietly unfolding, thanks to the risk-takers. From Michael Jackson's iconic appearance at the 1984 Grammy Awards to <a href="https://www.hommessingapore.com/culture/decoding-the-viral-soft-boy-aesthetic-of-frank-ocean-harry-styles-et-al" target="_blank" title="Decoding The Viral Soft Boy Aesthetic Of Frank Ocean, Harry Styles Et Al." rel="noopener">Harry Styles's</a> fearless embrace of traditionally "feminine" fashion at the 2019 Met Gala, the red carpet has become the stage for cultural milestones in their own right.&nbsp;
With award show season upon us, the anticipation for more viral-worthy men's red carpet outfits is heating up. In the meantime, let's revisit some of the most iconic men's red carpet outfits of all time.&nbsp;

At the 1984 Grammy Awards, Michael Jackson donned a sequin jacket, pants, and his signature white glove. That year, he ended up with the most wins and most nominations, taking home 8 out of the 12 categories he was nominated for. Photo courtesy of Ron Galella Collection via Getty Images.

Lenny Kravitz and Cindy Crawford turned heads as they arrived at the 1993 MTV Video Music Awards. Kravitz wore a striking silver bodysuit and green sunglasses, while Crawford wore a sheer black gown. Photo courtesy of Vinnie Zuffante/Getty Images.

Will Smith hosted the 1994 MTV Movie Awards, which he attended with his then-wife Sheree Zampino. Smith wore a black shirt and pants with a striking red jacket. Photo courtesy of Ron Galella Collection via Getty Images.

Matt LeBlanc attended the 1995 People's Choice Awards in a simple black suit with a leather vest. At the time, Friends had only come out with 1 season. Still, the Friends cast was in complete attendance upon accepting the award for Favorite New Television Comedy Series. Photo courtesy of Jim Smeal/Ron Galella Collection via Getty Images.

Dennis Rodman’s outfit at the 1995 MTV Video Music Awards was certainly an eye-catcher. He donned a silver tank top, grey pants, and silver accessories. Photo courtesy of Getty Images.

The 1999 Emmys was truly a star-studded event, featuring A-listers like Brad Pitt and his then-wife, Friends star Jennifer Aniston. Just 2 days before the event, Fight Club, in which Pitt starred, premiered. Photo courtesy of Getty Images.

Back when Justin Timberlake and Britney Spears were the it couple of the early aughts, the two attended the 2001 American Music Awards together. They arrived hand in hand in matching all-denim outfits and diamond jewelry. Photo courtesy of Getty Images.

Prince attended the 2005 Academy Awards with his then-wife Manuela Testolini. He donned a simple suit, with pale pink pants that matched Testolini's gown. Photo courtesy of Getty Images.

At the 2012 Met Gala, Marc Jacobs wore a daring lace dress by Comme des Garçons over white boxer shorts, when the theme was “Schiaparelli and Prada: Impossible Conversations.” While the designer sparked controversy over his sheer outfit, Jacobs explained on the event’s livestream that “Miuccia Prada is such a celebration of the unconventional.” “So it felt, like appropriate somehow,” he added. Photo courtesy of Lars Niki/Corbis via Getty Images.

Chadwick Boseman truly understood the assignment when the Met Gala theme was "Heavenly Bodies: Fashion and the Catholic Imagination.” He exuded regal sophistication in an Atelier Versace suit that featured a floor-length cape with gold cross embellishments and red tassels. Photo courtesy of Dia Dipasupil/WireImage via Getty Images.

Style icon Billy Porter’s outfit at the 2019 Academy Awards showcased his penchant for dramatic flair. The black velvet gown, designed by Christian Siriano, featured a full skirt, a long train, and a tuxedo jacket. Porter was later praised for starting a conversation surrounding gender norms within the fashion industry. Photo courtesy of Getty Images.

Harry Styles is known to take fashion risks, and he definitely brought his A-game to the 2019 Met Gala, when the theme was "Camp: Notes on Fashion." While some may have opted to play it safe with simple suits that year, Styles wore a sheer black blouse with pants from Gucci. Photo courtesy of Getty Images.

Jared Leto is known for his unforgettable fashion statements, but he took his unique style to a whole new level at the 2019 Met Gala. He wore a silk red gown with diamond embellishments designed by Gucci. But, the main attraction of his look was an exact replica of his head, which he carried around like an evening bag. Photo courtesy of Getty Images.

Off-White founder and Louis Vuitton menswear creative director Virgil Abloh was among the best dressed at the 2021 Met Gala. He wore a white suit with the word “Modernism” written across the jacket in light blue. Abloh also accessorized with matching light blue gloves, statement sunglasses, and a white hat. Photo courtesy of Getty Images.

Lil Nas X never fails to make an entrance with the most striking, pleasingly loud looks. At the 2021 Met Gala, he pulled off not one, not two, but three gold ensembles by Atelier Versace. Photo courtesy of Getty Images.

After 6 years of Met Gala no-shows, Justin Bieber celebrated his anniversary with his wife Hailey Bieber in style. He opted for a simple black blazer, baggy pants, white sneakers, and a black suitcase from his clothing brand, Drew House. Hailey, on the other hand, wore a black gown with a plunging neckline from Saint Laurent. Photo courtesy of Getty Images.

Maluma’s take on the “In America: A Lexicon of Fashion” theme for the 2021 Met Gala was an homage to American cowboy fashion. Sporting an all-red leather outfit, Maluma donned a Versace studded jacket with dramatic fringe, matching pants, and cowboy boots. Photo courtesy of Getty Images.

Timothée Chalamet is known for unapologetically experimenting with his wardrobe, pushing the fashion boundaries men are constrained by. At the “Bones and All” Red Carpet Event during the 79th Venice International Film Festival, Chalamet wore a memorable red halter pantsuit designed by Haider Ackermann paired with pointy-toed boots. Photo by Stefania D'Alessandro/WireImage courtesy of Getty Images.

Jeremy Pope’s Met Gala 2023 ensemble was a delightfully over-the-top homage to the late designer Karl Lagerfeld, who was honored at that year’s event. The star of the look was the floral embroidered cape that featured an illustration of Lagerfeld in a 10-meter-long train, courtesy of Balmain. Photo courtesy of Getty Images for the Met Museum/Vogue.

Bad Bunny may be recognized as the “King of Latin Trap” for his music, but he deserves equal praise for his daring fashion sense. At the 2023 Met Gala, he wore a custom all-white suit by Jacquemus. But, he added a touch of drama to an otherwise simple outfit, thanks to the backless detail and, of course, the 8-meter-long floral train. Photo courtesy of Getty Images.

At the 2023 Met Gala, Alton Mason channeled a Chanel bride in a custom Karl Lagerfeld ensemble designed by creative director Hun Kim. The look featured a lace corset, a beaded chiffon veil, and lace boots. Photo courtesy of Getty Images.

While the 2023 Met Gala saw a lot of all-black and all-white outfits with intricate details typical of Lagerfeld’s designs, A$AP Rocky opted for something a little different. Designed by Gucci, the look, which featured a black suit, tartan skirt, jeans, and 3 belts, was reminiscent of an outfit Lagerfeld wore to a Chanel runway show in 2004. Photo courtesy of Getty Images.

Saltburn star Barry Keoghan went for a punk look at the 2024 Golden Globe Awards. Styled by Ilaria Urbinati, Keoghan wore a red jacket and trousers from Louis Vuitton and accessorized with Tiffany & Co earrings. Photo courtesy of Getty Images.

The Best Men's Red Carpet Outfits Moments We'll Never Forget

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