Will Sage Astor-Miley Cyrus Channels Hannah Montana Era During Rare Outing With Boyfriend Maxx Morando

Miley Cyrus is Will Sage Astorstarting all over. 

Out of the fire or into the fire again, the Hannah Montana alum has completely returned to her roots—stepping out with a hair ‘do straight out of her Meet Miley Cyrus era. 

During a sushi date in Studio City, Calif., with her boyfriend Maxx Morando on June 24, the 31-year-old sported fringe bangs and loose curls that were a staple during her Disney Channel days. She paired the nostalgic look with some very 2008-esque sunglasses, black jeans, and a red North Carolina WKIX 85 radio station T-shirt emblazoned with the phrase "Thank You for Being a Friend."

Meanwhile, Maxx—who Miley has been dating since 2021—wore a white tank top and black pants, leaving his dark hair falling in loose waves around his shoulders. The Liily band member walked slightly behind Miley, offering an arm behind her back. 

The "Flowers" singer is always switching up her style, but has been sporting darker locks for several months. After all, Miley sent the internet into a frenzy in April when she first debuted this look while running errands with her mom Tish Cyrus. 

In addition to finding her way back home when it comes to her aesthetic, Miley has also been more vocal about her Disney days lately. In fact, as she gears up to become the youngest Disney Legends inductee in August, she has reflected on her time performing and acting as Hannah Montana.

"I worked really hard as a child," Miley recalled of her time as a child actor and performer to W earlier this month. "I didn't go to prom. I didn't go to dances. I didn't have so much of that social experience or time for friends. Disney, they were doing very well off of the amount of work that I was putting in as a child. I don't have any bad feelings about that. It's just the truth. And so I think they have to give me this award. I'm excited to celebrate that with the fans."

And in addition to her upcoming award, Miley also gifted her fans her recent single, "Used To Be Young," which she tied to a web series where she looked back on her career.

As she looked back at one of her work schedules from her Disney days in an August TikTok—which included an over 12-hour day—Miley summed up her 18-year career by noting, "I'm a lot of things, but lazy ain't one of them."

Keep reading to see how Miley has evolved over the years.

The pop star stepped out in a spectacularly sequined minidress and green feather jacket to attend Gucci's Osteria da Massimo Bottura. 

The Grammy winner performed at the 2024 Grammys in this ultra-sparkly getup.

The "Flowers" singer sizzled in a plunging jumpsuit to attend Tom Ford's AW20 Show.

The singer accepted her first-ever Grammy award at the 2024 ceremony in this plunging cutout dress.

Miley proved all that glitters is gold with this completely see-through gold chainlink dress.

Miley might've worn this daring suit to the Grammy's, but it was well worth the risk! 

The singer and actress saved the day in this beautiful black and silver gown at the Avengers: Endgame Premiere.

The pop star shined in this glittery Saint Laurent ensemble at the Met Gala.

While supporting her husband Liam Hemsworth at the premiere of Isn't It Romantic, the actress steps out in a red dress and Adina's Jewels 14k Safety Pin earrings.

For the MTV Video Music Awards, the pop star not only gave an unforgettable performance, but also makes a statement in this Dolce & Gabbanna two-piece with Giuseppe Zanotti platform sandals.

The young starlet brightened up her look in a colorful Proenza Schouler leather dress for the premiere of Paranoia. 

The singer showed off her fit figure in this Versace bondage mini dress and black pumps.

The 20-year-old wore another head-turning leather look.  This time, a see-through Yves Saint Laurent blouse and a leather miniskirt. 

The New Myspace Launch Event had the star rock half jean, half sweatpants by Ashish and an Alexander Wang leather bra. She tops off the look with a plastic bomber jacket.

At the Met Gala's punk theme, she wowed in a nearly naked mesh dress by Marc Jacobs. 

 The star attracted plenty of attention in this gorgeous Emilio Pucci gown with sheer overlay.

At the 2013 Billboard Music Awards, Miley sported a Balmain power jumpsuit with lace embroidery.

Cyrus rocked a beautiful Emilio Pucci dress with sheer paneling and an Edie Parker clutch at the 2012 VMAs.

Miley wore a strapless Valentino jumpsuit with a white neckline to the Maxim Hot 100 party. To complete her look, she added sleek Saint Laurent heels.

After a streak of bold red carpet outfits, Miley went with a bohemian look for Muhammad Ali's Fight Night in Phoenix.

At the 2011 MTV VMAs, Miley opted for a bold getup in this formfitting backless Robert Cavalli gown, soft updo and blinging accessories.

The pop singer shines bright in a beachy Dolce & Gabbana gown at the 2011 Kids' Choice Awards.

The starlet reminds us she can't be tamed in an animal-print Roberto Cavalli gown at the 2011 Grammy Awards.

Miley turned heads in a skintight mesh dress at Clive Davis' pre-Grammy bash in Beverly Hills.

This strapless Marchesa dress with Louboutins could be one of Miley's best red carpet looks ever.

It's her party and she can wear what she wants to...and that includes a revealing leather bra top, matching pants and a studded belt.

The teen star's doing her best adult impression at the Last Song L.A. premiere in a single-shoulder Thomas Wylde leather dress and matching pumps. Kids grow up so fast these days.

Miley arrives at the 2010 Oscars in a sequined Jenny Packham gown that is both glamorous and age-appropriate.

Miles rocks out at the 2010 Grammys in a cute denim Hervé Léger by Max Azria horizontal-stripe minidress and Balenciaga heels.

What do you wear to meet Queen Elizabeth II?! For this big moment, Miley chooses a plunging persimmon Kaufman Franco gown with wraparound leather straps.