Miley Cyrus is a shapeshifter. Honestly, if you look at a stack of miley cyrus photographs from 2006 and compare them to her 2024 Grammy sweep, you’d swear you were looking at five different people. It’s not just the hair—though we’ve seen everything from the brunette Hannah Montana waves to that viral 2013 pixie and the recent "Barbarella" blowout. It’s the energy.
People love to talk about her "rebellion" phase like it was some sudden accident. It wasn't. Those photos were a calculated, often painful, shedding of a skin that didn't fit anymore.
The Sheet That Shook the World
Let’s talk about the 2008 Vanity Fair shoot. You remember the one. A 15-year-old Miley, lensed by the legendary Annie Leibovitz, draped in a simple white silk sheet. Her back was bare. Her lips were red—the first time she’d ever worn that shade, according to her "Used To Be Young" TikTok series.
The backlash was brutal.
Parents were furious. Disney was "appalled." Miley actually apologized back then, saying she felt "embarrassed." But wait. Fast forward to 2018, and she basically retracted the whole apology on X (Twitter), posting the old New York Post cover with a caption that was... well, let’s just say she wasn't sorry anymore.
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What most people miss about those miley cyrus photographs is who was actually there. Her little sister Noah was literally sitting on Annie Leibovitz’s lap, helping her push the shutter button. It was a family day. But the public saw a "loss of innocence" because they couldn't separate the girl from the wig.
Why the Bangerz Era Photos Still Sting
If the Vanity Fair shoot was a crack in the dam, the Terry Richardson era was the flood. In 2013, the miley cyrus photographs coming out of Richardson’s studio were designed to incinerate the Disney bridge.
- The white tank top.
- The red cups.
- The constant, defiant tongue-out pose.
It felt chaotic, but Miley later described it as a "strategic hot mess." She was using the lens to demand a different kind of attention. She wasn't just being "wild"; she was reclaiming her body from a corporate machine that had controlled her image since she was 11.
Critically, these photos were polarizing. Some saw empowerment; others saw a formulaic "good girl gone bad" trope. But looking back, they were the bridge to her "Dead Petz" era and, eventually, the rock-and-roll sobriety of Plastic Hearts.
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The 2024 Grammy Glow-Up
If you want to see what "coming full circle" looks like, look at the photos from the 66th Annual Grammy Awards. Miley didn't just win her first Grammy for "Flowers"; she had five different outfit changes that felt like a retrospective of her entire life.
She hit the red carpet in a custom Maison Margiela "naked dress" made of gold safety pins. It was daring, sure, but it felt high-fashion, not desperate. When she performed "Flowers" in that silver fringe Tina Turner-esque dress, the photos captured a woman who was finally comfortable in her own skin.
"I've been working with Miley for a long time," her hairstylist Bob Recine told People. "We wanted a style that felt like it had a '70s, Barbarella feel while still having a modern, punk edge."
Paparazzi and the Power of the "No"
Miley’s relationship with the paparazzi has always been spicy. Just recently, in early 2026, she made headlines again for clapping back at photographers on the red carpet who were screaming at her to take off her sunglasses.
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"If you yell at me, I'll do the opposite," she famously told them.
She’s one of the few stars who has successfully transitioned from being a "target" of photography to being the "director" of it. Whether it's her street style in Saint Laurent or her self-directed music videos, she’s the one holding the remote now.
How to Track Her Style Evolution
If you're trying to understand her journey through images, don't just look at the professional shoots. Check out the contrast between these three distinct stages:
- The Disney Portrait Sessions (2006-2009): Look for the forced "bubblegum" smiles and the layers of glitter. These photos were about selling a product, not a person.
- The Liberation Period (2013-2015): These are the high-contrast, often gritty shots by photographers like Richardson or the "Wrecking Ball" stills. They're about shock value and breaking boundaries.
- The Modern Icon (2020-Present): Photographed by the likes of Philip Montgomery or Brianna Capozzi, these images focus on her voice and her maturity. The fashion is archival, the poses are statuesque, and the gaze is direct.
Miley’s story is etched into these pixels. She didn't just grow up in front of the camera; she fought it until it finally started seeing her for who she actually is.
Next Steps for Fans and Collectors
If you're looking to dive deeper into the visual history of her career, start by exploring the archives of Annie Leibovitz and Mick Rock, who captured some of her most "rock star" moments. For high-resolution archival prints, checking the Getty Images editorial collection for "Miley Cyrus portrait sessions" provides a year-by-year breakdown of her physical transformation. If you're more interested in the fashion side, tracking her collaborations with Maison Margiela and Gucci via Vogue Runway offers the best look at how she uses clothes to tell a story.