March 14, 2021, was a weird time for the world. We were a year into a global shutdown, and the music industry was desperately trying to figure out how to do an awards show without it feeling like a glorified Zoom call. Then came the opening of the 63rd Annual Grammy Awards.
The screen flickered to life. No massive pyrotechnics. No backup dancers in masks. Just a circular stage, a funky bassline, and a man in a black leather suit with a green faux-fur boa that would soon become the most talked-about accessory of the decade. This was the night of the Harry Styles Grammys 2021 appearance, and honestly, it changed the trajectory of his career from "boy band alum" to "global icon."
He didn't just show up. He set a tone.
The Performance That Launched a Million Boas
People still talk about that rendition of "Watermelon Sugar." It wasn't the studio version you’d heard a thousand times on the radio while stuck in traffic. It was grittier. Jazzier. Dev Hynes (Blood Orange) was there on the stage, adding this cool, alternative texture that made the pop hit feel like something pulled out of a 1970s funk club.
👉 See also: Biggest Concert Venue in the US: What Most People Get Wrong
Styles has this way of moving that feels both rehearsed and completely spontaneous. It’s a trick. You’ve probably noticed how he interacts with the camera—it’s never desperate. He looked like he was having the best time in the room, even though the "room" was a socially distanced tent outside the Staples Center with just a handful of other nominees like Dua Lipa and Taylor Swift watching from small round tables.
The leather suit was custom Gucci, designed by Alessandro Michele. It was a statement. By pairing a hyper-masculine material like leather with a soft, whimsical green boa, Styles continued his streak of blurring gender lines in fashion. It wasn't just about the music; it was about the silhouette.
Breaking Down the Win
Later that night, things got serious. Styles was nominated for three awards: Best Pop Solo Performance, Best Pop Vocal Album (Fine Line), and Best Music Video ("Adore You").
When he won Best Pop Solo Performance for "Watermelon Sugar," the reaction was a mix of "finally" and genuine surprise. He beat out some massive heavyweights. We’re talking about Taylor Swift’s "Cardigan," Billie Eilish’s "Everything I Wanted," and Dua Lipa’s "Don't Start Now." That is a brutal category. To come out on top of that list is no small feat. It basically validated the entire Fine Line era.
He was humble, too. During his speech, he thanked his manager, Jeffrey Azoff, and made sure to mention how much he admired the other artists in the category. It felt sincere. Kinda refreshing.
Why the 2021 Grammys Felt Different for Harry
For years, there was this lingering stigma attached to One Direction members. Critics loved to dismiss them as manufactured products. But the Harry Styles Grammys 2021 moment was the final nail in the coffin for that narrative.
You can’t fake that level of musicianship.
The academy members, who are notoriously snobby about "pop stars," clearly saw the craft in Fine Line. The album wasn't just a collection of singles; it was a cohesive, psychedelic-pop journey influenced by Joni Mitchell and Van Morrison. Winning that Grammy meant he was officially part of the "serious artist" club.
The Controversy Nobody Remembers
Believe it or not, there was actually some drama. Not everyone was thrilled about the win. Music Twitter—which is a scary place at the best of times—erupted because "Watermelon Sugar" was technically released in late 2019. Because of the way Grammy eligibility windows work, it felt "old" to some fans who were rooting for newer tracks.
👉 See also: Why Back to Black Amy Winehouse Song Still Gut-Punches Us Two Decades Later
Also, the Recording Academy was under fire (again) that year for the Weeknd’s "After Hours" snub. It created this weird atmosphere where Harry’s win was sometimes used as a talking point for why the Grammys are out of touch. But if you look at the performance in a vacuum, it’s hard to argue he didn't deserve a seat at the table.
The Fashion Legacy
Let’s talk about the Boas. Plural.
He didn't just wear the green one. For the red carpet—or what served as the red carpet that year—he wore a plaid blazer with a purple boa. It was a "clashing colors" nightmare that somehow looked like the most sophisticated thing on the planet.
- The Green Boa: Worn during the performance. High energy. Iconic.
- The Purple Boa: Red carpet elegance.
- The Black Leather: A nod to Elvis, maybe? Or just a way to make the colors pop.
Within 24 hours of the broadcast, searches for "feather boas" reportedly spiked by over 1,500% on fashion platforms like Lyst. That is the "Harry Styles Effect" in raw numbers. He doesn't just wear clothes; he moves markets.
What Really Happened Behind the Scenes
Fun fact: The show’s producers were terrified of the technical logistics. Because of COVID-19 protocols, the bands had to be set up in a way that kept them separated but allowed them to play live. Styles and his band had to rehearse in a highly controlled bubble.
Ben Winston, who produced the 2021 show, has mentioned in interviews that they wanted the opening to feel like a "live lounge" rather than a massive arena show. They wanted intimacy. They got it. When Harry stripped off the boa mid-song and threw it to the floor, it wasn't just a move—it was a signal that the night had officially started.
Interestingly, Harry actually stayed to watch other performances. You could see him nodding along to Billie Eilish and HAIM. He didn't just do his set and vanish into a black SUV. That matters in an industry where ego usually wins.
The Long-Term Impact
Looking back from 2026, the Harry Styles Grammys 2021 event was the bridge to Harry's House. It gave him the confidence to go even weirder and more personal on his next record. It proved that you could be a massive pop star and a "musician's musician" at the same time.
It also cemented his relationship with Gucci, which would eventually lead to his own "Ha Ha Ha" collection.
If you’re looking to understand why he’s currently one of the few artists who can sell out stadiums for 15 nights in a row, you have to go back to that night in 2021. It was the moment the general public—not just the stans—realized he was the real deal.
Key Takeaways for Fans and Creators
If you’re an aspiring artist or just someone who loves the culture, there are a few things to learn from Harry's 2021 sweep.
- Reinvention is key. Don't just play the song people know; give them a version they didn't know they needed. The funk-heavy "Watermelon Sugar" was a masterclass in refreshing a brand.
- Visuals are 50% of the battle. The boa wasn't just a prop; it was a character. It made the performance meme-able and shareable, which is how you survive in the digital age.
- Respect the peers. Harry’s interactions with other artists that night showed that being a "nice guy" in the industry isn't just a gimmick—it builds long-term respect with the voters.
Check out the high-definition footage of the performance if you can find it. Pay attention to the percussion and the backing vocals. It’s a masterclass in live arrangement. Then, go listen to Fine Line again, specifically the B-sides like "Canyon Moon" or "Sunflower, Vol. 6." You’ll hear the DNA of that Grammy-winning night all over them.
The next step is simple: watch the 2023 "Harry's House" Grammy sweep and compare the two. You’ll see an artist who went from proving he belonged to proving he owns the place. Out-of-the-box thinking is what keeps an artist relevant five years later. Styles is the blueprint for that.