The Hannah Montana 20th Anniversary Red Carpet Was A Nostalgic Fashion Disaster

As Miley Cyrus' "Hannah Montana" character Miley Stewart once said, "... Changing can be scary, but it's a part of growing up. It's how we find out who we are and who we're gonna be," per BuzzFeed. A lot has changed since "Hannah Montana" first hit the Disney Channel in 2006, and since then, Cyrus has clearly discovered who she is. Yet, it seems that she's more ready than ever to get back to her roots. On March 23, the pink carpet was rolled out for the big premiere of the "Hannah Montana" anniversary special. The stars came out for the occasion, and their outfits reminded us of the good old days — but sometimes in a bad way. 

When it comes to fashion, one era's trash is a past era's treasure. This truth was on full display at the premiere. Stars were eager to sport early aughts-inspired looks in honor of the days when "Hannah Montana" was everywhere. And, while these looks were definitely a bit dated today, they would have been perfect two decades ago. Cyrus hit the red carpet looking stunning in a glittery silver evening gown layered over a "Hannah Montana" t-shirt in a look that worked in 2026 just as well as it would have in 2006. Some other stars, instead, prioritized Y2K vibes over fashion-forward 'fits. Were these less-than-fashionable looks an inevitability of paying homage to early aughts style? Yes. Did they make us nostalgic for our youth? Also yes. We'll call that "the best of both worlds."

"Call Her Daddy" host Alex Cooper clearly has a very vivid memory of her youth, because this look took us right back to 2006. The tinted sunglasses, the sparkly, skinny scarf, the cropped, fringe-covered pants: everything about this look would be perfect costuming for a period piece set when Fergie and Justin Timberlake were all over the radio. Is this a good look? No. But, 20 years ago, it would have been best-dressed at the Kids' Choice Awards.

Shanica Knowles remembers "Hannah Montana" firsthand, so it's no surprise that she captured the vibe of the series so perfectly with her ensemble. A pink sequined dress paired with cowboy boots, a white and red cowboy hat, and a fluffy shawl would have made the worst-dressed list at any other red carpet event in 2026. On the "Hannah Montana" pink carpet, however? She obviously remembered Miley Cyrus' words of wisdom: "Pink isn't a color, it's an attitude" (via CBS News).

While the "Hannah Montana" 20th anniversary red carpet was full of folks channeling the early aughts with style straight out of "Lizzie McGuire," Matt Peterson went in a different direction. He seemingly built his ensemble based on the question: What if Björk's iconic swan dress came out of a claw machine? Said swan dress was definitely an unforgettable Y2K fashion moment. This was, nevertheless, a pretty odd pick for this or really any conceivable occasion. But, hey — he managed to steal the spotlight at an event with plenty of fun looks.

As one of the worst-dressed celebrities of 2025, it wasn't a shock to see Lainey Wilson in one of the worst looks at the "Hannah Montana" 20th anniversary premiere. It was, however, a shock to see her without her usual cowboy hat, which would have been perfectly on-theme. The former "Hannah Montana" impersonator's sheer, sparkly jumpsuit didn't really give off the 2006 vibes many other stars were going for. Sure — she was definitely channeling pop star energy, but this look didn't feel like the right fit.   

JoJo Siwa didn't have her big break on "Dance Moms" until 2014 — a few years after Miley Cyrus hung up her "Hannah Montana" wig. Still, the vintage JoJo look she donned on the pink carpet definitely fit in with "Hannah Montana"-era style. In an oversized polka dot jersey, a pleated miniskirt, chunky polka dot sneakers, and a bow in her hair, Siwa couldn't have been crowned best dressed no matter where she went in this 'fit. In pink, purple, and plenty of whimsy, though, she captured "Hannah Montana" vibes.

Scott Hoying of Pentatonix fame gave major "Hoedown Throwdown" vibes as he graced the pink carpet with his hubby, Mark Manio. While we can appreciate Hoying's take on the theme, this wide-leg, dark-wash Canadian Tuxedo with a white tank top, red neck scarf, and cowboy hat put a particularly silly twist on the country music-inspired look. Overall, this ensemble definitely ventured into costume territory, rather than a red carpet-ready 'fit.

Britney Spears did not wear this glitzy green minidress to the Grammys afterparty in 2006, but we can definitely imagine it. Gizele Oliveira looked like a lacy disco ball in chartreuse on the pink carpet. In 2026, this look inarguably looks dated. Yet, between the color, the silhouette, and all that sparkle, it definitely captured a certain early aughts energy that you just don't see anymore. A pink bedazzled flip phone would have been the perfect way to accessorize this look.

It's been a while, but we definitely remember people wearing button-down shirts in the early 2000s. So, why former "American Idol" finalist David Archuleta skipped the shirt when putting on his black and white suit for the pink carpet is certainly unclear. The sparkly jacket and subtle pop of pink gave this look the perfect understated nod to "Hannah Montana." Unfortunately, the lack of shirt distracted from the rest of the look and just left us confused.

The underwear as outerwear trend has been all over red carpets this year, as illustrated by some of the worst-dressed celebrities of 2026 so far. Kaci Conder's "Hannah Montana" 20th anniversary premiere outfit probably leaned into this trend more than any look we've seen. The draped-down red dress over the falling-off bra over the lavender corset? There was a lot going on here, and it didn't make much sense or give us Y2K vibes. Besides — who would layer undergarments like this? We don't think Hannah Montana would.