Kate Middleton Fashion Risks That Paid Off

Princess Catherine has many titles: Princess of Wales, Duchess of Cambridge, Countess of Strathearn, and even Baroness Carrickfergus. However, there's no doubt that fans of Catherine have given her the unofficial title of fashion icon. Her style has influenced people across the globe, and the "Kate Effect" comes out in full force every time she wears something new. Within minutes, these pieces have sold out online, and dupes pop up in cheaper stores around the world. In fact, Catherine has become somewhat of a fashion influencer and has reportedly added an incredible £1 billion to the U.K.'s fashion industry (per Newsweek).

But while Catherine has connections to some of the best clothes and designers that money can buy, it's no secret that she has to adhere to a strict royal dress code. For the most part, Catherine seems to keep herself on the right side of the royal rule book. Royal expert Bethan Holt even went so far as to state that Catherine has "taken a lot of tips" from the late Queen Elizabeth II (via Us Weekly).

However, it seems as if the princess is also eager to forge her own path in the royal world, which is why she sometimes takes big risks when it comes to her fashion choices. And you know what they say — with great risk comes great reward!

When she wore full-length opera gloves

Princess Catherine and her husband are extremely conscious of their environmental impact. And in an effort to slow down the process of climate change and stop unnecessary clothing waste from piling up in landfill, the princess has proven that she's the queen of re-wearing her outfits. This refreshing decision has been celebrated by fans, especially as Catherine has re-worn outfits over 85 times in recent years (per Town & Country). In 2023, she even re-wore a dress she had already worn back in 2019 — but this time she added a risky twist that nobody expected from her.

As Catherine donned the white Alexander McQueen gown to the 2023 BAFTA Awards, fans noticed that she had added some full-length black opera gloves into the mix. The daring gloves stood out against the white dress and gave off an air of Hollywood glamour.

Unfortunately, her fashion risk divided opinions online. While one Twitter user wrote, "Those gloves look dreadful with that gown," Genevieve James, the creative director at royal glove supplier Cornelia James, had a different opinion. She told People, "Opera gloves are transformative; they have enormous leverage. They turn any event into an occasion and a dress into a statement."

When she wore a Gucci blouse backward

Although she's a well-respected fashion icon, there's no doubt Princess Catherine has dealt with fashion faux pas every so often. And while you could say that wearing your clothing backward is a mistake, it seemed to work in her favor in 2019. During an unannounced visit to Henry Fawcett Children's Centre in London, the Duchess shared toys with the children and spoke to doting mothers while wearing some black high-waisted pants from Jigsaw and a purple pussy-bow blouse from Gucci (per Entertainment Tonight). And while the whole ensemble looked well put together, it didn't take internet sleuths long to realize that she was actually wearing the blouse backward.

As fashion fans dug through the internet to find the Gucci blouse, they eventually discovered that the buttons were designed to be worn at the back of the shirt (per Marie Claire). When Catherine wore it, she wore the buttons at the front of the shirt — perhaps intentionally, or perhaps not. And fashion journalist Anthony McGrath told Insider India that Catherine's no stranger to switching things up with her clothes: "Kate enjoys adjusting outfits to suit current trends. She will quite often add a bow, remove a keyhole, or change the length of skirts or sleeves to make them her own."

However, it seems as if the princess preferred the wrong-way-around look, as she re-wore the blouse the same way during an Instagram Q&A in November 2020.

When her sailing shorts were very short

Although her royal calendar is full of public appearances, Princess Catherine never says no to a sports event. She played field hockey while studying at St. Andrews, and since then she's become one of the most athletic members of the royal family. And while it was clear that she was as happy as a clam while playing tennis with Emma Raducanu in September 2021, Catherine's athleisure outfits are scrutinized every time she makes her way onto a court, pitch, or field for events like this.

As the princess knows that everyone will have an opinion on what she wears, she's started to take risks with her athleisure outfits. That's exactly what happened in 2019 when she attended the King's Cup Regatta. For this royal outing, Catherine took to the water in a charity sailing race against her husband — and Prince William ultimately reigned victorious when Catherine's boat was disqualified from the race (per Town & Country). But it wasn't Catherine's sailing skills that got everyone talking. Instead, it was her legs.

As Catherine donned athletic shorts for the event, fans couldn't help but comment on her refreshing change of style. One fan wrote on Twitter, "No one freak out, but Kate Middleton wore shorts? Yassss queeeeeennnnnn." Another tweeted, "Of course shorts are an appropriate sporting attire, and it's great to see them promoting a healthy, active outdoor lifestyle." So it seems as if this risk paid off.

When she wore a see-through dress for a fashion show

Before she became the Princess of Wales, Catherine was a normal teenager. Although she planned to study at the University of Edinburgh, she reportedly had a "dramatic and sudden change of heart" that saw her take a year out before enrolling at the University of St. Andrews (per Marie Claire). It was here that she met fellow student Prince William, and the pair struck up a friendship.

When Princess Catherine was a student, her style was "typical college girl," according to Reader's Digest. But one fashion risk in 2002 changed everything for her when she was asked to take part in a charity fashion show. For this event, she strutted down the runway in a Charlotte Todd dress — which just so happened to be see-through. Because of this, her black bra and underwear set was visible underneath, and this didn't go unnoticed by Prince William.

According to E! News, William shelled out $275 to get a front-row seat when he learned that his friend would be modeling in the fashion show, and couldn't believe his eyes when he saw Catherine in the barely-there ensemble. He reportedly turned to his friend, Fergus Boyd, and said, "Wow, Fergus, Kate's hot!" Over the next few months, William and Catherine's friendship turned romantic. And while you won't find Catherine wearing anything like this today, it's fair to say that this fashion risk certainly worked in her favor.

When she wore wedges

Although it's not known where King Charles stands on the footwear front, the late Queen Elizabeth II had some strict rules and regulations when it came to her shoes. The late monarch even employed someone to break in her new shoes. This was her dressmaker and close friend, Angela Kelly — and Kelly confirmed this in her book, "The Other Side of the Coin." She wrote, "A flunky wears in Her Majesty's shoes to ensure that they are comfortable and that she is always good to go. And yes, I am that flunky. The queen has very little time to herself and not time to wear in her own shoes, and as we share the same shoe size it makes the most sense this way" (via Town & Country).

Catherine's grandmother-in-law also had strong opinions on wedges. A source close to the royal family revealed, "The queen isn't a fan of wedged shoes. She really doesn't like them and it's well known among the women in the family" (via Vanity Fair). However, Catherine broke Elizabeth II's strict rule many times during her reign, and it seems as if she's continuing her wedge adventure even today.

While it's believed that she prefers this style of shoe over other options, such as stilettos, it's also been suggested that Catherine wears these shoes for the sake of her foot health (per Hello). Apparently, wedged shoes provide stability and reduce the chances of an ankle twist.

When she went against the color scheme at the BAFTAs

As a member of the royal family, Princess Catherine's life is governed by rules. The royal gift policy outlines the rules she must follow when receiving or accepting gifts, and she's even had to perfect the "Duchess slant" (per PopSugar). However, Catherine seemed to go against the rules when she turned up at the 2018 BAFTA Awards. As revealed by The Hollywood Reporter, attendees were encouraged to wear black in solidarity with the Time's Up movement. And while most of the celebrities who walked the red carpet adhered to the rule, there was one person who didn't: Princess Catherine.

Instead, Catherine turned up in a beautiful forest-green Jenny Packham gown. The dress was adorned with a black sash around the waist, but her decision to go against the rules made her stand out from the crowd, and critics were quick to call her out for not showing her support.

Although her dress divided fans, theories surrounding her decision soon came to light. As members of the royal family are meant to be politically neutral, many wondered whether Catherine was simply not allowed to align herself with something that was politically motivated. And while it's not officially enforced, etiquette expert Alexandra Messervy told InStyle, "Generally it is thought that black is not usually worn unless in mourning" (via Marie Claire). So Catherine could have found herself in the midst of two conflicting rules for this event.

When her red dress stood out from the other royals

Since making her way into the limelight, Princess Catherine has proven that she can rock an extremely varied color palette. And while Marie Claire has found that the princess rarely wears orange, she's certainly no stranger to wearing red. She did just that in June 2012 when she attended Queen Elizabeth II's Diamond Jubilee in a bright red Alexander McQueen dress with a matching hat. When choosing her outfit, Catherine probably didn't realize that it was a risk — but an article later published by The Daily Mail suggested that it was a risqué move.

The event, which saw the royal family float down the River Thames on the royal barge, was an impressive affair to celebrate the queen. Because of this, the writer of this article suggested, "If ever there was an occasion when Kate should have opted for a more subdued look, then this was surely it." They continued, "Yes, she looked stunning. But when in the queen's company, less is definitely more." And as the queen and Camilla, the queen consort, opted to wear white and cream outfits respectively, Catherine stood out even more.

However, critics were quick to shut down the article. Fans of Catherine typed out their support for her outfit, and one wrote, "Kate's red really worked well with the queen's stark white. It seemed to me that Camilla was the oddball and could have tried blue."

When she wore this white dress to Royal Ascot

In 2016, Princess Catherine made her debut at one of the U.K.'s most prestigious events, Royal Ascot. Per Royal Ascot, "Ladies must wear a hat or headpiece with a solid base of 4 inches in diameter in the royal enclosure." And when Catherine attended her first Royal Ascot event, she wore a white lace dress by Dolce & Gabbana and coupled this with a beautiful saucer-style hat (per Page Six). The next year, she wore an almost identical white lace number, this time from designer Alexander McQueen. Again, she adhered to the rules and wore a matching white hat. Unfortunately, her second dress didn't go down as well as the first.

Although there were just a few small differences between Catherine's two Ascot dresses, one of those differences made a big impact — especially as royal fans believed her to be breaking another one of Ascot's strict rules.

According to Vogue Australia, critics of Catherine's outfit claimed that her dress was too short and too sheer for such an occasion. However, the event's rules about dresses and skirts state that they "should be of modest length defined as falling just above the knee or longer." This means that Catherine's high-necked and knee-length dress followed all of the rules. Fans seemed to agree, as cheaper dupes of her Alexander McQueen soon popped up everywhere (per Evening Standard).

When this floral number divided opinions

Princess Catherine knows what she likes when it comes to her style, and that's why she's pledged allegiance to some of her favorite designers. According to Town & Country, both Catherine and Meghan Markle are fond of Stella McCartney, Alexander McQueen, Monica Vinader, and Erdem. However, Catherine's decision to wear a floral Erdem dress in October 2015 certainly didn't go down well.

Although Catherine is no stranger to wearing bold block colors, she rarely chooses to go bold with her prints — especially when wearing a full-length gown. But that's exactly what she wore for the 100 Women in Hedge Funds gala. And while fans were particularly intrigued to see that Catherine was wearing such a bold pattern, many critics soon took to social media to air their grievances with the dress. One user wrote on Twitter, "Not my favorite floral dress on Kate today. Too old for her! A bit frumpy — reminds me of purple floral she wore when expecting Charlotte."

Catherine didn't seem too phased by the backlash to her dress, though. Since then, Catherine has continued to support the brand and has worn numerous Erdem dresses. She even wore the brand for the Commonwealth Day service in March 2023. And per Marie Claire, this dress may have served as a subtle dig toward her estranged sister-in-law, Meghan Markle.

When people thought she wore her dress backward

As we've seen already, Princess Catherine is no stranger to wearing her clothes backward. When she attended the Addiction Awareness Week gala in London in 2019, fans of the duchess wondered whether she'd done the same thing again — as it seemed as if she was wearing her off-the-shoulder Barbara Casasola dress the wrong way around. Even though Catherine had previously worn the dress in 2016, it garnered more attention the second time around. And to the untrained eye, the dress looked strange as the zip seemed to be in the middle, and at the front, of her chest. Normally, you'd expect the zip to be at the back.

However, Cosmopolitan did some digging and discovered that this was all part of the design. They found a listing of the dress on a website and learned that the dress was designed to offer this unique and unusual detail. And while it could be said that wearing such a dress was a fashion risk, there's no doubt that Catherine's decision to wear such an outfit worked in her favor.

One Daily Mail reader commented, "That dress is gorgeous and suits her tall, slender frame. She needs to get one in every color." 

When she embraced a menswear moment

There are certain things that Princess Catherine won't wear. But this list isn't exhaustive, as the princess has been known to experiment with her style over the years. She's taken fashion risks, and sometimes these have worked in her favor — especially when she's embraced a menswear moment.

Although Catherine can normally be found wearing gorgeous gowns and skirt-and-shirt combos that ultimately sell out in minutes, she's often tried to incorporate more masculine pieces into her closet. To kick-start their three-day trip to Boston for Prince William's Earthshot Prize initiative in November 2022, Catherine opted to wear an Alexander McQueen pantsuit teamed with a black turtleneck. This look was far removed from her usual attire, but she didn't stop there. For the second day of their trip, Catherine continued the pantsuit theme and wore a burgundy Roland Mouret pantsuit coupled with a pink pussy-bow blouse.

Fashion and royal expert Christine Ross told Newsweek that Catherine's "ascent into pantsuits seems to follow her development into a very-involved working royal. We often see these pantsuits at more business-formal events, where her outfit may fit in better with the people she is meeting." Nevertheless, it's been impressive to see Catherine ditching the feminine for the more masculine.