It’ll come to no surprise to anyone that’s ever stepped within a miles radius of me from the year 2006 to now that I am a hard-core Miley Cyrus fan.
That’s because you’ll either hear Miley Cyrus or Hannah Montana through my headphones or blasting out the sides of my car, see me manage to sneak in some merch or reference into something I’m wearing that day, or hear me blabbering on to the first person that’ll listen about Miley’s latest album, most recent cover shoot or re-birth of Hannah Montana - and these are just my 2026 conversation starters, there’s many more in the bank.
From the first episode of Hannah Montana airing on Disney Channel in 2006 to now, the evolution of Miley’s career has not only stuck with me throughout my early adolescence and into adulthood, but has also shaped me as a person.
Whilst that might sound a little dramatic, I’m not exactly ‘poppin’ lockin’, polka dottin’ day to day (although I do listen to Hoedown Throwdown probably more than the average 30-something year old), Miley's life has directly mirrored the cultural, societal and personal shifts that my generation has grown up with.
From the school halls to navigating modern-day life as a woman in the 21st century, Miley and her on-screen counterpart, Hannah, walked us hand in hand through the moments that make up becoming a young person and venturing into adulthood. We’ve essentially navigated it alongside her, whether it be through the screens of Disney Channel or in a more raw way through the lenses of paparazzi cameras or intrusive social media.
So when I found out Miley was taking to the Disney Channel studio to tape the 20th-anniversary episode of the show, I was beside myself.
Not only because I tend to have this kind of visceral reaction to anything Miley Cyrus does - trust me, I’ve followed her throughout her whole career and proudly fought for everything she does (even the Dead Petz album - IYKYK) - but because it really put the evolution of her as an artist into perspective for me, coming full circle at a time when many of her fans are now in a similar position of reflection.
Ok, most of us aren’t revisiting the multi-million-dollar show that propelled our careers into the stratosphere, but we are at a moment when we're looking back at the childhood and tween moments that shaped us.
Working in fashion throughout my career, it got me thinking about the years that were turning points for our generation and experimenting with style, and then it dawned on me - those growing up watching and listening to Hannah Montana were massively shaped in ways we probably didn’t realise at the time.
The show was not only a turning point for the channel ($$$), but it also culturally explored art and fashion in ways that hadn’t been done before, and therefore influenced us as young people in ways generations hadn’t had.
How Hannah Montana shaped fashion
When it comes to expression, how better to do this during our formative years than experimenting with fashion, and that’s exactly what Miley's character led with during the series run on Disney Channel, notably something that hadn’t been done before her time.
BH (before Hannah, a time that I don’t recall fondly), mainstream media that was aimed at teens was not aspirational. I’m talking (and truly no hate against any of these as Drake and Josh is still a solid watch in my very humble opinion), Nickelodeon’s Drake and Josh, The Amanda Show, and Zoey 101, or even the likes of Lizzie Maguire, That’s So Raven and Even Stevens protagonists were regular children, stardom wasn’t introduced to us and most importantly fashion was influential, sure, but not aspirational as well.
Landing on our screens in 2006, Hannah Montana was a show whose central theme was a regular high-school girl who was secretly living a double life as Hannah Montana, a global teen pop sensation. Notably, the on-screen character didn’t stray from Miley’s life massively at all. The character was originally called Alexis during casting, but Disney were so taken with how the young star embodied the role that they named the protagonist Miley Ray. So was she ever living a double life, or did she evolve into the protagonist? Miley is Hannah, and Hannah is Miley.
© Stephen ShugermanThe show navigated family, Miley’s dad, Billy Ray Cyrus, even starring as her on-screen father, Robbie Ray; friendships; relationships; growing up; moving away; and much more, mirroring her fans' lives at the time.
And whilst other shows of the time focused solely on day-to-day life, Hannah and Miley were reaching for the stars. It might sound cheesy to say, but it really was the first of its kind for tweens, inspiring them with art in a way that hadn’t been communicated on their level before.
The same goes for Hannah and Miley’s style.
The double life became a trend in itself; it went beyond the plot of each episode's story lines by being portrayed in the way the characters were styled.
Hannah’s wardrobe was also pivotal to the show’s narrative. The immersive walk-in-wardrobe (to the max) showed young fans that expression through fashion, art and creativity in ways that no other tween show was accurately representing or had delved into since. What she wore told us who she was at the time, whether that was Hannah or Miley. The same goes for how our generation uses fashion to express themselves today.
Her style was explorative, trend-setting - not following, and more importantly, was fun and a safe space for those finding their own identity and feet within the modern world. The protagonist’s Iconic (and enduring if you ask me) pieces included the perfect mix of skinny scarves, sequin tops, cowboy boots, chunky jewellery and layered tops - leaning into bold clashes and colourful textures. The outfits were aspirational but achievable for the masses. Because who didn’t want to walk around embodying the iconic lyric … “I might even be a rockstar…”
© WireImageInstead of full-on high-fashion pieces, outfits often combined things like jeans, sneakers, and simple tops with one standout item (like a sequined jacket or sparkly boots). Miley Cyrus has even acknowledged that the style was deliberately relatable and commercial, which helped make the character hugely influential in kids’ fashion at the time.
Hannah’s enduring influence
Also, how did I even get this far in without mentioning that Hannah Montana leading lady Miley Cyrus just is (and I am happy to be challenged I am this confident) one of the strongest female vocalist of our generation, but an incredibly talented songwriter, that poetically adapts naturally from genre to genre throughout her discography all yet whilst remaining absolutely true to her artists identity. Hard to do, right? But she’s made it look so easy that we almost take it for granted.
The same can be said of her fashion evolution, finding her identity within Hannah and beyond. There has not been another fictional star who has influenced Zellenial/ Gen Z style like her.
For many young viewers, the show became a kind of first “style playbook.” The show helped popularise a specific look: casual basics + sparkle + layered accessories. That aesthetic showed up in school wardrobes, Halloween costumes, and even early social media style posts during the creation of social platforms.
Interestingly, Miley Cyrus later reflected that while the look wasn’t always “her,” it became something bigger culturally, because fans didn’t just watch it, they participated in it.
This is exactly how fan Lorian De Sousa got hooked.
If you survive and thrive within the realms of not only the Miley-verse but also major pop culture, you would have heard of the social media account @outofconexthannahmontana. Run by devoted fan Lorian De Sousa, the account has made a mark online and beyond, sharing Hannah Montana lore, iconic memes that the fans live for, one-of-a-kind merch and experiences. More recently, Lorian was even invited to Hollywood to watch the live recording of the Hannah Montana 20th Anniversary (major Miley fan, say what?).
But if there was going to be a voice that was able to speak for Hannah’s generation of fans worldwide, it’d be Lorian De Sousa, who, from a child, was immersed not only in the story but also in the sparkle. “I grew up with an intense obsession with wearing a single glove, and it wasn’t because of Michael Jackson, but Miss Miley Cyrus. More specifically, Hannah Montana and her signature pink leather fingerless glove,” he tells H! Fashion.
"The look from the show’s third season had such a chokehold on me that, as a child, I would only wear one of my black mittens and wander around the playground in the middle of winter pretending to be her. I also credit her with my enduring obsession with Dr. Martens boots.”
In 2011 (clearly a hard year for me as a teen, given the line I'm about to type), the curtain fell on Disney Channel’s Hannah Montana. I wasn’t the same, but it was clearly time to evolve forward with Miley, and that’s just what fans did. However, the Hannah style remained something that we all carried with us. Rhinestone logo t-shirts? ‘WooOhoo YeaaAaaH’ (as Hannah would say)! Cowboy boots? Duh! Layered tops and vintage denim jackets from Vinted? So Hannah! There was that experimental fashion I'd grown up with, and it wasn't going anywhere now that the show was over.
And I’m not the only one who thought so.
“Hannah Montana is a generational show we were lucky to experience. The fact that we can still quote iconic lines 20 years later says it all! It made you believe you could be a pop star, even when you were sat in maths class - and who didn’t dream of Hannah’s walk-in wardrobe?” Radio 1 DJ, social media presenter and all-round fellow Miley-Hannah fanatic Jodie Bryant told H! Fashion.
“But along with the Doc Martens, singular pink glove, sequins and blonde wig, the concept shaped how we see identity today. The idea of balancing a ‘normal’ life with something bigger is now everywhere - Hannah was the blueprint. She made you feel like you get to be whoever you wanna be (yes, The Best of Both Worlds lyrics have stood the test of time). The hype around the 20th anniversary proves we are the Hannah Montana generation - and those songs still absolutely pop off … Rockstar is legit one of my favourite songs of all time ”
Has Miley re-lit the Hannah flame?
Well, if you ask me, the flame never went out.
Yes, Miley had a complicated relationship with Hannah when the show ended in 2011 - but can you blame her? The same could be said for me and my friends looking for parties, sneaking out and just growing up. But for Miley it was being done in the public eye and the tie between her and Hannah needed to be cut.
Reflecting on it now as a lifelong fan, it’s clear there was never a real separation though. Miley continued her career into Hollywood and the music industry in experimental ways that hadn’t been done by artists before her. Experimenting with genres with each album release was so Hannah. The confidence to try something new, build new identities and play around with art was something that was inherently Hannah coded.
The flame is still burning. According to Spotify, in 2025 Hannah Montana music was streamed nearly 10.7M hours globally – that’s more than 1,220 years of Hannah Montana in a single year with over 276,000 users having Hannah Montana in their top 5 artists that year. And for fashion? Double layering is back, sales of Y2K styles continue to soar year-over-year with The Washington Post reporting that brands that lean into this style like Hollister have outperformed their name sake stores (like Abercrombie & Fitch) in the last quarter. And on social media, the Y2K hashtag has been viewed more than 10.1 billion times on TikTok.
The influence lives on.
Miley’s latest musical project and album ‘Something Beautiful’ really reminded me, as a fan, of the reason I fell in love with her back in 2006 - she was bold, creative and herself. Something that was portrayed through Hannah's fashion and art, and now into Miley's career. Throughout her ‘Something Beautiful’ era, she relied heavily on fashion to express herself (Ok Ms Montana), with a sleek, archival high-fashion aesthetic. She wore designers like Thierry Mugler, Jean Paul Gaultier and Alexander McQueen.
© GC ImagesSubtle flex, but I was even lucky enough to see her perform in Paris wearing archival Mugler and Alaia… and yes, I’ve not been the same since. It was clear to me then that Miley, through the power of expression and confidence gained with Hannah, continues to build on and experiment with her genres of fashion and style. The same expression and confidence that's inspired fans to have confidence with fashion and dressing since 2006.
Fast forward to today, and the reason I'm writing this is that on Tuesday, 24th March 2026 (yes, I’m counting down the hours and days), Miley will return to our screens on Disney Channel to celebrate 20 years of Hannah Montana. There’s been no better time to look back at the impact the shows had. But clearly, and maybe even more subtly, without us noticing, the show has dictated fashion, shopping and style for a cohort of a generation.
So I, hopefully many others too, can say they owe a lot of their confidence in fashion and art to the fictional character that Miley brought to life, and you know what, hearing her singing Best of Both Worlds dressed in a full Diesel look by Glenn Martens in 2026 will heal me.
