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The Most Outrageously Dressed Celebrities at the American Music Awards: From Sweatshirts to Umbrella Hats

As the 2025 American Music Awards (AMAs) approach, excitement is building not just for the musical performances but also for the fashion statements that will grace the red carpet. The AMAs have long been a showcase for bold and sometimes outrageous fashion choices, making it a highlight for both music fans and fashion enthusiasts alike.

### A Legacy of Fashion Statements

Over the years, the AMAs red carpet has transformed into a stage for dramatic ensembles and risqué outfits. While many stars have dazzled in stunning attire, others have stumbled into the realm of fashion faux pas, leaving us with unforgettable moments that are often discussed long after the event. As we gear up for this year’s ceremony on May 26, DailyMail.com has compiled a list of the worst-dressed celebrities from past events, reminding us that not every fashion choice is a hit.

### The 50th Anniversary: A Mixed Bag

The 2024 AMAs were particularly noteworthy as they celebrated the awards’ 50th anniversary. Despite the significance of the occasion, some celebrities missed the mark with their fashion choices. Singer Raye, 27, who performed at the event, opted for an unusually casual look, wearing a baggy dark brown sweatshirt paired with a mint green button-up mini skirt. Her choice of black mules, red lipstick, glasses, and statement earrings did little to elevate her ensemble, making it one of the more talked-about outfits of the night.

Sophia Culpo, sister of model Olivia Culpo, also found herself on the wrong side of fashion history with an outdated sequin blazer dress that failed to impress. The ensemble felt more like a relic than a statement, showcasing how even the most glamorous events can lead to fashion missteps.

### Standout Fashion Fails

Television personality Ajani Scott made headlines for her bold choice of a short blue dress with a dramatic plunging neckline. While the intention may have been to make a statement, the execution left much to be desired, overshadowing her presence on the carpet.

In 2022, the AMAs featured a mix of standout looks alongside some notable misses. Kim Petras, 32, donned an all-denim outfit that was less than flattering. The studded jean ensemble flared out with a mermaid train, paired with a chunky denim belt and a tiny purse, creating a look that many deemed overwhelming. Similarly, singer Pink, 45, took a risk with a colorful, sparkly dress that resembled a fridge, complete with a high neck and thigh-high slit, but ultimately fell flat.

### The 2021 Fashion Scene

The 2021 AMAs were no stranger to fashion fails either. Becky G, 28, sported a semi-80s frilled purple mini dress with black trimming and shoulder pads, which featured strips of fabric fastened with dated clips. This look showcased segments of skin but failed to resonate with the audience. Meanwhile, Billy Porter, 55, made headlines for his bright blue Tiffany suit, complete with an umbrella hat and a nipple flash, proving that sometimes, less is more.

Machine Gun Kelly also made an impression in 2021 with a purple suit adorned with metal needles, a choice that sparked conversations about the boundaries of red carpet fashion.

### A History of Outrageous Choices

The AMAs have seen their fair share of outrageous fashion choices over the years. In 2017, makeup guru Patrick Simondac, known as Patrick Starr, stood out in a fringed green jumpsuit that was more distracting than stylish. Bebe Rexha, 35, left little to the imagination in a nearly-naked dress that clung to her body, pushing the envelope of red carpet attire.

Bella Thorne made the worst-dressed list in 2016 with a rock star look that included a leather bra and a black suit jacket, paired with strappy heels. Similarly, Z LaLa shocked attendees in a PVC and net creation, complete with a gravity-defying hairstyle that resembled a halfpipe.

Even actress Katherine Heigl faced criticism in 2005 for her baggy all-ivory look, which included a tank top, drawstring pants, and a massive jacket that felt too casual for the occasion.

### The 2025 AMAs: What to Expect

As we look forward to the 2025 American Music Awards, set to be held at Fontainebleau Las Vegas, the anticipation for both performances and fashion is palpable. With a history rich in both stunning and questionable fashion choices, only time will tell which stars will deliver memorable looks and which will find themselves on the worst-dressed list once again. The red carpet promises to be a battleground for style, where creativity and risk-taking will either shine or falter.

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