Awkward Princess Eugenie Moments That Were Caught By Millions

Princess Eugenie has had her share of awkward moments, and when you're a royal, the public is always watching. Prince William and Kate Middleton can't go anywhere without having every minute caught on camera. And even after they moved to the United States, Prince Harry and Meghan Markle can't seem to escape the press.


Other more low-key members of the royal family are also on just about everyone's radar, and Eugenie is no exception. The youngest daughter of Prince Andrew (yes, that Prince Andrew) and Sarah "Fergie" Ferguson, Eugenie grew up in the public eye, and has had to deal with some major public scandals and stresses. Her parents famously got divorced in the '90s, and she and her sister have consistently been criticized for their wardrobe choices; Eugenie's really had to maneuver the press and the public all while trying to live a semi-normal life.

It's no wonder then, that due to years in the spotlight, Eugenie has had some slip-ups. Some awkward moments have been because of the weather, others were fashion faux pas, others were downright tense family interaction. So hold onto your hats, because here are the awkward Princess Eugenie moments that were caught by millions.


The insane winds on Princess Eugenie's wedding day caught everyone off guard

Wedding days are stressful — from the flowers to the guest list to the seating arrangements, it's no wonder that brides can go from angel to demon in two seconds. But one aspect of the day that even the bride can't control is the weather, and Princess Eugenie found herself in a horrifically awkward situation on her big day. 


According to Cosmopolitan, a storm hit the UK on Eugenie's October wedding day. As such, the winds were truly out-of-control, and guests and wedding party members alike were literally blowing over. In pure British form, many of the women in attendance wore fascinators — so cue the photos of the intricate hats flying off of heads and men running after them. Not the cutest look for a wedding if we do say so ourselves. 

Of course, as Eugenie walked up the steps of St. George's Chapel in Windsor, she was subjected to the harsh gusts of wind. Her wedding dress and train needed some assistance, and her father's jacket was spotted flapping in the wind. The whole scene was a bit awkward, but luckily there wasn't any rain.


This painfully awkward appearance turned heads in Princess Eugenie's direction

Princess Eugenie has undergone a stunning transformation. She grew up in the media spotlight, but as the young daughter of Prince Andrew and Sarah Ferguson, she mostly appeared in public as a cute kid with royal parents. But things changed for the princess after Prince William's wedding to Kate Middleton, and not in a good way. As noted by People, Eugenie awkwardly turned heads with her 2011 wedding day attire. 


Specifically, Eugenie wore a blue and green dress from designer Vivienne Westwood, and her hat was made by famed milliner Philip Treacy. However, the status of the designers couldn't save Eugenie from awkward run ins, side-eye glances, and mean headlines. The dress's over the top extravagance and the fascinator's flower/feather combination was truly not a good look, and the princess was subjected to some pretty insane criticism after the fact. "[She] got hammered in the press and it was a little unfair," said Charlie Anderson, a stylist who was brought in to work with Eugenie for a year to help "turn around" her style after the fashion slip-up. Not an awkward moment that many will forget.

Princess Eugenie's awkward '90s outfit was on full display at this royal event

There are a couple outfits that us '90s kids will never be able to live down. We're scarred from brightly-colored turtlenecks. We were forced to wear fanny packs before they "cool," and the pastel dresses that we had to put on every Easter Sunday haunt us. 


Princess Eugenie was one such '90s kid, and the awkward moment when she appeared at St. George's Chapel in Windsor Castle to celebrate her grandfather's 80th birthday was one to remember. The young princess was in full lime green attire, beading included. The look was topped off with a skinny headband and a tiny purse (think Lizzo but far less trendy). That wasn't the only time that the outfit made an appearance, either — Eugenie was spotted in a similar getup at the Queen Mother's 101st birthday celebration the same year. 

Eugenie clearly has a sense of humor, because she took to Instagram to poke fun at her fashion choices. "Bea and I are laughing hysterically after contemplating what on earth was in our handbags that day going to church," she wrote. "The shoes, the headbands... yes to the '90s."


Things got a little awkward when Princess Eugenie's sister failed to help her with her wedding dress

Every wedding is bound to have slip-ups, but Princess Eugenie's big day was full of awkward details — and this one is cringey. Eugenie's older sister, Princess Beatrice, served as the maid of honor, a role that's tasked with helping the bride maneuver her dress and assisting her throughout the day. But according to the Daily Mail, things got awkward when Eugenie made her way to the carriage at the bottom of the venue's staircase. 


The wind was blowing and the princess's dress had a long train, but instead of helping her sister out with the dress, Beatrice awkwardly stood on the steps as her sister struggled to climb into the carriage. You can watch the video here. Beatrice is stepping from side to side, perhaps wondering if she should be at the bottom of the stairs helping the bride out, or if she should remain standing next to her mother. 

The same sort of slip-up was seen later in the wedding celebrations, as Beatrice was consistently not the first person to help the bride with her dress. It's ok, just awkward.

Princess Eugenie dealt with awkward family drama on her wedding day

Family is complicated, and no family knows that better than the royals. Weddings can bring tension to the forefront, and that was certainly the case on Princess Eugenie's big day. 

As noted by Express, things got really awkward for the bride because of her mother's relationship with Prince Philip. Sarah Ferguson famously and publicly got divorced from Prince Andrew years ago, and although she mended her relationship with Queen Elizabeth, Philip reportedly never forgave her. "Because he dislikes Fergie so much, he almost backed out of Eugenie's wedding just so he wouldn't have to see her," Express reported. "In the end, the Duke showed up for his granddaughter's big day and even posed for several wedding photos that also featured the Duchess of York." 


But apparently, Philip was not pleased. A royal source told Express that it was the first time they'd been pictured together in 26 years, and the prince didn't speak to Fergie the entire day. We can't imagine just how awkward it was for the bride, who after all, was just trying to enjoy her big day.

Princess Eugenie had an awkward moment with the Queen when she was a kid

Having doting grandparents can be great, but things are probably not super easy when your grandmother is the beloved monarch of the United Kingdom, a fact that Princess Eugenie is more than aware of. Even at a very young age, she seemed to be held to a high standard, so things got a little awkward when baby Eugenie got told off on camera by Queen Elizabeth II. Yes, you read that correctly. 


According to New Idea, the Queen was spotted telling poor Eugenie off after she stood on the monarch's foot while on a family trip at Balmoral Castle. The footage was filmed by the BBC in 1992, and the little princess can be seen standing next to the Queen while her sister and older cousins are riding ponies. "Ouch! It is my foot you are standing on!" the Queen exclaimed to the tiny princess, who looked all of a foot tall. 

Stills of the very grainy 1992 footage can be seen via the Daily Mail, and while it could be an enduring moment between grandmother and granddaughter, it's a little awkward to watch.

Things got really awkward when Princess Eugenie's big day was almost overshadowed by this news

Body language says a lot, and the physical distance between Princess Eugenie and her soon-to-be husband and Prince Harry and Meghan Markle during her wedding ceremony may not have been by accident. As noted by The Sun, the awkward tension was palpable on the big day for this very specific reason: Meghan told the royal family about her pregnancy at the ceremony. Yikes. 


Royal authors Andy Tillett and Dylan Howard explained in their book Royals at War that Eugenie was livid about Meghan's decision to announce such news on her big day, as was her mother, Sarah Ferguson. "Meghan put her foot in it when she decided that it would be the ideal moment to announce that she and Harry were expecting their first child," the authors wrote. "This was a huge social gaffe, even if you were not a royal."

Although royal sources have denied that such an announcement took place, it's safe to assume that the news didn't sit with Eugenie well.

This moment between Princess Eugenie and Kate Middleton was awkward

Kate Middleton came onto the royal scene, pretty quickly stole the spotlight, and has continued to make headlines throughout her time as a working royal. But the attention, the praise, and the adoring fans she's received haven't reportedly been an easy pill for Princess Eugenie to swallow. As noted by Express, "a number of reports have indicated in the past that Kate has not always been the best of friends with the princesses," Eugenie and her sister, Princess Beatrice


The bluntness of the royal pecking order was on full display at the 2018 Trooping of the Colour celebration, marking Queen Elizabeth's birthday. Not only was Meghan Markle a scene stealer with her rule breaking attire, but Kate was also standing front and center on Buckingham Palace's balcony. Eugenie, by comparison, was standing off to one side looking particularly awkward on an otherwise happy royal occasion. An insider told the Daily Mail that Eugenie has felt "snubbed" on occasion, and has been made to feel like a "walk-on part in royal family life" (via Express). Yikes.

Wedding day jitters are normal, but Eugenie had to help her new husband in this awkward slip-up

Wedding days often are accompanied by a lot of emotions — excitement, nervousness, anticipation. And it looks like the nerves got the best of Princess Eugenie and Jack Brooksbank, because the couple endured a very awkward (yet very touching) moment during their wedding ceremony. According to People, "the couple ran into a problem when it came time for Jack to slip Eugenie's Welsh gold wedding band on her finger: the ring didn't quite fit." Uh oh. 


The report included that Brooksbank struggled quite a lot to push the wedding band onto his bride's finger, and perhaps due to the awkwardness of the moment, made a silly face. Fortunately the princess rescued her sweet husband-to-be, and helped adjust the ring into position. 

But the moment, for as awkward as it was, was part of a very loving and enduring dynamic between the couple. "When he's having a hard time with the ring, Eugenie maintains her stance and is very patient with him," body language expert Patti Wood told Good Housekeeping. "This couple has a strong, unbreakable love for another." Cute.

Prince Charles and Princess Eugenie had an awkward moment

It was the awkward moment not caught on camera that did the talking. As noted by Express, Prince Charles — the heir to the British throne — is reportedly tightening the purse strings, and is being very picky about who is "in" and who is "out" in the royal family. And as the royal circle is getting smaller, "Princess Eugenie is not considered a senior royal despite being tenth in line to the throne and granddaughter of the Queen, and reports now suggest it is due to Prince Charles." Yikes. 


As she's technically not a working royal, Princess Eugenie reportedly is not being offered the Privy Purse, which is the royal private income. The awkward dynamic between Charles and his niece was, to an extent, caught on camera in December 2020. During one of the very rare public appearances of Queen Elizabeth (due to the coronavirus pandemic), royal family members were present with choice few excluded — Eugenie being one of them (via Express).

Princess Eugenie made an awkward comment about her husband

It's not unusual for people to give readings during wedding ceremonies. And although Princess Eugenie seems to very much love her husband, the reading that she chose in his honor turned a lot of heads — and not in the best way. According to People, Eugenie selected a reading to dedicate to her new husband from the iconic American novel The Great Gatsby; specifically, she chose a passage that described the main character, Jay Gatsby, and his alluring smile as it reminded her of her newlywed. 


Before you say anything, yes, we should acknowledge that it's a little weird that a British princess chose an American passage for her wedding day. But aside from that, people took to Twitter to point an important aspect of the story: The Great Gatsby is a tragedy that ends in death, corruption, and destruction. That...doesn't exactly scream "wedding" to us. "That was really weird that Eugenie chose a wedding reading that compares her husband to Jay Gatsby," a Twitter user wrote, via the Independent. "Did she finish the book? Because it doesn't end well for Gatsby." Definitely an awkward choice.

Princess Eugenie's wedding had yet another awkward moment

According to The Hits, Princess Eugenie's wedding day was not only upstaged by both the rumors of Meghan Markle's pregnancy and the awkward tension between Sarah Ferguson and Prince Philip. It was also was made worse when the wedding souvenirs featured the name of the wrong sister. Yes, you read that correctly. 


Specifically, the Buckingham Palace Royal Instagram account posted a photo of a commemorative mug that was available for purchase, but instead of including Eugenie's name, the original post and mug included Princess Beatrice's name instead. "This exclusive mug issued in commemoration of the wedding of HRH Princess Beatrice of York and Mr. Jack Brooksbank is now available for purchase by following the link in the description," the caption read. Not surprisingly, the post was promptly taken down, but we can't imagine just how awkward that must have been for Eugenie and her husband.

Princess Eugenie got into some trouble after this awkward moment

We've all made social media mistakes, there's no doubt about it. We've posted pictures on our stories to grab the eye of one particular person. We've also made errors in our captions, and fallen subject to over-editing. But Princess Eugenie actually got into some serious hot water over her Instagram activity, in part because she revealed behind-the-scenes snaps of the royal life that are technically off-limits. "I recently got in trouble for posting a picture of Papa in a corridor of the palace that was off-limits to the public," she told Vogue. The photo in question was a snap of Prince Andrew before the Trooping of the Colour, in which he was serving as Colonel of the Grenadier Guards for the first time. 


Not only did Eugenie land in a sticky situation, but the post continues to be awkward for the princess due to the comments that people left. "Delete this," one person said. "Why that pedophile still free?" and "Shame of the royal family," wrote others, all to do with the allegations against Prince Andrew and his inappropriate involvement with Jeffrey Epstein. Talk about awkward.

This body language expert broke down the awkward dynamic between Princess Eugenie and her parents

Even when the cameras are rolling and people put their most gracious foot forward, awkward body dynamics can do the talking. To that end, not only was there tension between the members of the royal family during Princess Eugenie's wedding ceremony (just look at Queen Elizabeth and Prince Philip's facial expressions), but the official portrait of the royal wedding party spoke volumes. 


According to The Mirror, the "enormous gap" between Eugenie and her parents in the official photo gave millions of viewers an awkward experience. "Sadly Eugenie's mother Sarah was put at the outer edge of the line-up, with Beatrice filling the huge gap between mother, father and daughter," body language expert Judi James, told OK (via The Mirror). "The distance between Eugenie and her parents means her father is at the very far end of the line-up, which makes Eugenie's closest family members look rather distant." 

To make matters more awkward, the groom's family was very close to the new couple, creating a very tense scene. What caused such tension? Will anyone truly know? The royal family is quite the mystery.