Harry Styles has had one of the most impressive musical transformations of the past decade. From his days in One Direction, where he was part of one of the biggest boy bands in the world, to carving out his solo career, Styles has consistently surprised and captivated fans with his evolving sound and style. His music is a blend of pop, rock, and even a little bit of soul and folk. It’s not just the sound that’s evolved over the years, though—it’s the themes he explores in his lyrics, his unique style, and the way he interacts with his fans.

As Harry has matured both personally and artistically, his music has reflected the changes he’s gone through. Whether you’ve been following him since his One Direction days or discovered his solo work more recently, his music speaks to people across ages, from the younger crowd in their 20s to older fans in their 30s and 40s. The songs on this list show how Harry Styles has managed to stay relevant, grow as an artist, and connect deeply with his listeners.

Here are five standout songs from Harry Styles that highlight his musical evolution.

1. Sign of the Times (2017)

When Harry Styles released “Sign of the Times” in 2017, it immediately signaled to the world that he was ready to leave behind his boy band image and make music on his own terms. The song, which was the lead single from his debut self-titled album, is a perfect mix of classic rock influences and modern pop. The soaring melody, the dramatic production, and the powerful vocals set the tone for what Harry’s solo career would become.

The lyrics are a bit cryptic, but they carry a strong message about the state of the world and the challenges people face. The line “Just stop your crying, it’s a sign of the times” became an anthem for anyone who was feeling overwhelmed or uncertain, as it encouraged listeners to keep going despite the chaos around them. The song’s theme of surviving difficult times and finding hope is universal, and it resonated with people of all ages.

Why it’s iconic: “Sign of the Times” was a bold move for Harry. It wasn’t just a departure from One Direction’s bubblegum pop—it was a statement about who he wanted to be as an artist. It showed that Harry wasn’t afraid to experiment with new sounds, take risks, and explore deeper, more complex themes in his music.

2. Adore You (2019)

Fast forward to 2019, and Harry Styles’ second album, Fine Line, marked another shift in his sound. “Adore You” was one of the album’s most beloved tracks, and it was impossible to miss why. With its groovy bassline, catchy melody, and upbeat vibe, “Adore You” had all the makings of a pop hit. But what really sets this song apart is its sweet, romantic lyrics and the overall feeling of warmth it gives off. It’s a song about loving someone unconditionally, and the emotion behind Harry’s vocals makes that message even more powerful.

The music video for “Adore You” became iconic in its own right, thanks to its whimsical narrative about a boy and his pet fish. The video, which tells the story of Harry’s character trying to connect with the fish, has been interpreted as a metaphor for how we all long for love and connection, no matter how unconventional the form it takes.

Why it’s iconic: “Adore You” perfectly blends retro influences with contemporary pop music, and it showed a different side of Harry’s personality. It’s light, fun, and joyful, and it’s a track you can’t help but sing along to. But it’s also heartfelt and vulnerable, showing Harry’s ability to balance playful moments with deeper, more meaningful ones.

3. Falling (2019)

If “Adore You” was the carefree track, then “Falling” from the same album was the emotional opposite. This is one of Harry’s most vulnerable songs, and it shows a completely different side of him. The lyrics are deeply personal, dealing with self-doubt, regret, and heartbreak. In the song, Harry sings about losing himself and feeling like he’s become someone he doesn’t want to be: “What am I now? What if I’m someone I don’t want around?” The song is slow, haunting, and emotional, allowing Harry’s raw vocals to take center stage.

The music video for “Falling” is just as impactful. It features Harry in a room filling with water, which is a powerful visual metaphor for being overwhelmed by emotions. It’s a scene many people can relate to, especially when you’ve gone through tough times and felt like you were sinking.

Why it’s iconic: “Falling” is Harry at his most raw and open, revealing personal struggles in a way that’s relatable to anyone who’s ever dealt with self-doubt or heartbreak. It shows how much he’s grown as an artist, not just musically but also in terms of his emotional depth and willingness to be vulnerable with his fans.

4. Watermelon Sugar (2019)

After the emotional depth of songs like “Falling,” Harry hit us with a burst of energy in the form of “Watermelon Sugar.” This track, from Fine Line, became the ultimate feel-good anthem, and for good reason. Its infectious chorus and vibrant instrumental arrangement make it impossible not to smile when you hear it. The upbeat rhythm, combined with its funky guitar riffs and Harry’s playful delivery, gives it an undeniable charm.

Despite its light-hearted sound, “Watermelon Sugar” carries a sense of nostalgia and warmth. Many listeners interpret the song as a tribute to the simple pleasures in life—summer days, good company, and those small moments that make life special. It’s a perfect escape, especially when you need a pick-me-up.

Why it’s iconic: “Watermelon Sugar” is Harry’s answer to the need for joy and fun in music. In a world filled with uncertainty, it’s refreshing to hear a song that’s just pure happiness. The track also became hugely popular during the summer of 2020, and it quickly became the soundtrack of that strange, isolated period in time. Its positive energy made it a perfect companion for those long, hot summer days.

5. As It Was (2022)

Fast forward to 2022, and Harry Styles released “As It Was” as the lead single from his third album, Harry’s House. The track is another shift in his sound, this time embracing a more synth-pop style. But don’t let the upbeat tempo fool you—the song’s lyrics carry a more melancholic tone. “As It Was” is about personal change, nostalgia, and the feeling of being out of place. The line “You know it’s not the same as it was” speaks to the bittersweet realization that life is constantly evolving, whether we’re ready for it or not.

The song’s music video, where Harry spins in circles, visually represents the feeling of being stuck or caught in a whirlwind of emotions. It’s a perfect metaphor for how many of us feel at different points in our lives, trying to keep up with change while still longing for the past.

Why it’s iconic: “As It Was” marks yet another evolution in Harry’s sound, incorporating new influences while staying true to the themes that have always resonated with his fans. It’s a song about transition, and it speaks to anyone who’s ever had to navigate change, whether it’s in their career, relationships, or personal life.