Sarah Ferguson Fashion Mishaps That Stunned Royal Fans

Sarah Ferguson has struggled with fashion since she first joined the royal family in 1986, thanks to her marriage to the now-disgraced Prince Andrew. She's been in the spotlight for decades, and throughout those years, Ferguson has stepped out in outfits that stunned royal fans — and not in a good way. Granted, being a contemporary of the eternally fashionable Princess Diana is no easy feat. To make matters even harder, Diana frequently broke royal fashion rules and was that much more loved for it. 

To throw Ferguson a bone, she was strutting her stuff in the late '80s, an era that was notoriously unfortunate for fashion. From shoulder pads to ruffles — and don't forget about those puffed sleeves — Ferguson had to navigate this decade with a trail of paparazzi following her around. It can't have been easy. However, others (cue to Diana, once again) still managed to pull together timeless outfits. This wasn't the case for Ferguson. Even after the '80s were long over, Ferguson made sartorial mistakes. To be fair, other royals have flubbed, too. Catherine, Princess of Wales had fashion mishaps that stunned royal fans. Similarly, other royal women wore outfits that were beyond controversial. So Ferguson's not alone in making mistakes, but some of her clothing flops are hard to look away from. 

The contrast to Princess Diana's style was painfully evident when Sarah Ferguson attended a polo match in Windsor in 1986. Ferguson wore a blue-and-white gingham outfit with a white belt and coordinating hat. The fashion mishap was that Ferguson looked like she was wearing a Halloween costume rather than an actual outfit. Conversely, Diana wore a sleek, beige skirt suit that was much more effortless, particularly at an outdoor sporting event. 

In 1988, Sarah Ferguson attended the gala charity performance at the Strand Theatre in London with Prince Andrew. For the occasion, Ferguson opted for a navy gown that was a mix of showgirl sleeves with a Victorian, bustled gown. There was so much going on it's hard to pinpoint exactly what the dress was trying to convey beyond excess. The drawstring sleeves showed a lot of skin for a royal woman. Plus, they didn't balance with the historic element of the rest of the dress, and the opera gloves were just another eyesore on this busy look. 

For the late Queen Elizabeth II's 60th birthday, Sarah Ferguson attended a party in Covent Garden wearing a voluminous gown. There's a lot to say about this look, and some of it worked. The white, off-the-shoulder top portion of the gown was really flattering on Ferguson, so she gets points for that. However, the skirt of the dress was disastrous. Not only was the color blocking of navy and black a curious mash-up, but the skirt was deeply wrinkled. It made the gown, which was full and dramatic, appear unkempt and sloppy. 

Sarah Ferguson was a woman in red when she attended a performance at the Royal Opera House. While Ferguson loved a bold color palette, which is fine, this red dress was too much of a good thing. The dress was a busy structure of lace and frills. On top of that, the plunging neckline was a tad too risqué for a royal woman. The dress, as a whole, was overwhelming. Rather than Ferguson wearing the dress, that red, lacy dress was wearing her.

The Royal Ascot has famously been an opportunity for the royal family to showcase some of their most daring outfits. While bold choices are usually a hit, Sarah Ferguson's navy, white, and green dress at the Royal Ascot was a chaotic combination of styles. There were heavy pleats in the skirt, followed by loads of decorative trim. The bodice of the dress was so busy when placed in proximity to the pleats and there were just too many visual stories for the dress to come off as chic and cohesive. 

Imagine the late Queen Elizabeth II wearing a black, leather jacket. The concept is inconceivable. So when Sarah Ferguson stepped out in a glossy, black leather jacket in 1996, royal fans were amazed. That year, Ferguson published her memoir, "My Story," and was on a book tour, stopping in Pasadena, California, to sign copies for fans when she wore the controversial coat. Leather is certainly uncommon among royal women, particularly when constructed as a black, moto-style jacket, so Ferguson's look pushed back against royal fashion rules. 

Sarah Ferguson looked sensational when she attended the Cipriani Deutsche Bank Concert With Kanye West in June 2006. She paired a bustier top with a black satin skirt and polished things off with a choker necklace embellished with tasseled decals. While she objectively looked lovely, the outfit was very risqué for a royal woman. The low-cut neckline on the sleeveless bustier was attention-grabbing, combined with the black satin of the outfit. It was both a sensual and bold choice for Ferguson, one that the late Queen Elizabeth II probably didn't approve of. 

Sarah Ferguson had an unfortunate wardrobe malfunction while in Rome in 2017. While attending a cocktail party at the Quirinal Palace, Ferguson's sleeve caught on the hem of her dress, and when she lifted her arm, she completely exposed her underwear. Unfortunately for Ferguson, the Daily Mail got their hands on the pics, and they now live eternally on the internet. It certainly wasn't Ferguson's fault in any way; instead, it was just one of those embarrassing moments that got captured by paparazzi. 

For the 2018 wedding of her daughter, Princess Eugenie, to Jack Brooksbank, Sarah Ferguson had a fashion win and a fashion mishap in one outfit. The win was her sensation, figure-hugging emerald green Emma Louise dress. It was flattering and elegant at once. The mishap was her Jess Collett hat. While it was tonally appropriate, the stiff bow at the back looked like wings on Ferguson's head, and gave the otherwise stylish outfit a comical twist.