Kate Middleton Looks That Were Surprisingly Outdated

Catherine, Princess of Wales, is widely regarded as one of the most fashionable members of today's royal family. For years, royal watchers far and wide have not only admired her sartorial moves, but have done their best to emulate her style. Time and time again, she's set trends and boosted fashion brands; the "Kate effect" is real.

While Catherine does take some fashion risks that take her outside of her style comfort zone, her outfits usually feature at least one of her fashion go-tos. Prince William's other half has long been a big fan of a classic pointed-toe pump, modest figure-hugging dresses, structured jackets, and so on. Hey, if it ain't broken, why fix it? 

However, some of her other go-tos aren't as timeless as she might hope. In recent years, Catherine's been caught wearing skinny jeans, ankle boots, and real fur — not exactly the most fashion-forward moves, to say the least. Yes, even someone as stylish as Princess Catherine is bound to rock an outdated look every now and again. 

If there's one outdated style trend Princess Catherine seems to cherish more than any other, it's skinny jeans. Though Gen Z and the fashion industry have declared skinny jeans an outdated millennial trend, with wide-legged jeans becoming increasingly popular since the mid-2010s, Catherine still dons the fitted pants for more casual royal engagements. For example, in May 2023, the princess attended an outing in support of the Big Help Out initiative. Alongside Prince William and all three of their children, Catherine dressed down in an outdoorsy ensemble appropriate for the field day occasion. Her look included high-waisted, washed black skinny jeans with cargo pockets, an equally outdated chambray blouse, a braided belt, and brown leather Chelsea boots. The princess' outfit felt very Katniss Everdeen with a dash of HBO's "Girls."

Later that year, Catherine once again wore skinny jeans to an event. The Princess of Wales went to a SportsAid fitness workshop in dark-wash skinny jeans that hit a few inches above her ankles, showing off her stylish Veja sneakers. She sported a fitted white scoop-neck top beneath a stunning cobalt double-breasted blazer with antique gold buttons. While the outfit wasn't bad, a sleek pair of high-rise straight leg jeans would have elevated Catherine's ensemble in a major way.

In October 2023, Princess Catherine and Prince William hosted 100 young delegates at an event for World Mental Health Day. William wore an understated suit and tie combo, whereas Catherine went with a school bus yellow blazer that would've been right at home in the '80s or '90s. While some trends from that era have come back with a vengeance, one could argue this particular coat felt a bit too dated. The royal paired the bright coat with black pants and a black blouse. The color palette was reminiscent of a bumblebee. Or a sunflower. Or, yes, a school bus. 

Catherine's wide-leg slacks and long-sleeve crewneck shirt were classically stylish, and even the silhouette of the long-line blazer was a fashionable cut. However, the color story simply made the whole thing feel dated. Swapping the school bus yellow for a different pop of color would have been the easiest way to save the outfit. That said, the bold shade could have worked better with, say, a rich violet ensemble beneath the jacket.

There are elements of Princess Catherine's 2023 Commonwealth Day ensemble that are absolutely stunning, but there's one glaring factor that's arguably outdated. While there's been some discourse about peplum silhouettes making a comeback, the hip-accentuating cut is still quite divisive. Nonetheless, Catherine decided to embrace the contested style during the Commonwealth of Nations springtime celebration.

The Princess of Wales wore a navy skirt suit by Erdem that featured lovely repeating floral embroidery across the jacket and skirt. The hem of the elegant, coquettish trumpet skirt ended at Catherine's mid-calf. The shape of the flared hem was mirrored by the matching jacket, which featured peplum panels at the sides and exaggerated structured shoulders at the top of the ensemble. The princess drew further attention to her peplum number by styling her brown mane in a tidy chignon topped with a royal blue wide-brimmed hat. The fit and flare repetition from head to toe created a look that encouraged the eye to scan Catherine, but the ensemble may have achieved the same effect — and looked sleeker — without the protruding peplum.  

In May 2022, Catherine, Princess of Wales, stepped out in another outfit that wasn't entirely outdated, but it did feature an element that is not as on-trend as it once was. During an event at the British Design Museum, Catherine presented the Queen Elizabeth II Award while wearing a jewel-toned green dress by Edeline Lee. The loosely fitted dress featured a mock neck silhouette with a hem that fell just below the knees. The half-sleeves were cinched with bow ties, and Catherine's waist was encircled by a matching fabric belt with two oversized gold buckles. A larger square buckle aligned with the center of the princess' frame, while a slightly smaller rectangular buckle sat off to the side of her waist. 

While built-in belts were in vogue throughout the 20th century, it's now more common to pair a separate belt with a dress to cinch the waist and create a break in the top and bottom of the garment. Additionally, oversized belt buckles were all the rage in the 2000s but fell out of favor the following decade. However, when big belt buckles become fashionable again — remember, fashion is cyclical — it seems Catherine will be more than ready. 

In April 2022, Princess Catherine wore another unflattering garment that not only left a lot to be desired, silhouette-wise, but looked dated. For her first joint engagement with Princess Anne in support of maternal healthcare, Catherine selected a monochromatic beige ensemble. She donned an A-line skirt with a mid-calf hemline and a shrunken blazer — the outdated garment in question. The jacket's front panels featured a mirrored embroidered design that was cut off by a built-in belt at the waist. The hem of the blazer flared out for a subtle peplum cut that emphasized the A-line silhouette of the skirt. The matronly outfit didn't exactly feel age-appropriate for Catherine, especially given her trendsetting history.

The princess' outfit may have been considered more on-trend if the blazer's silhouette was longer and more relaxed. Additionally, the built-in belt gave the closed jacket a stuffy appearance. Without it, the embroidery would have been unobstructed — though the blazer could have done without the odd design, too.

Perhaps the most outdated ensemble Catherine, Princess of Wales, has worn to date was the dress she donned for the departure ceremony at Lynden Pindling International Airport during her and Prince William's March 2022 Caribbean tour. The princess showed up in a yellow and white patterned dress by Alessandra Rich that was oh-so retro — and not exactly in the best way.

The garment featured an abstract floral pattern, subtle metallic polka dots, ruffled puff sleeves, a pleated peplum waist, a bow at the center of the scoop neckline, pearl buttons down the midline from the bust to the knee, and a built-in belt with a circular metal buckle. Needless to say, there was more than a lot going on with this dress. 

It definitely could've been a chic look once upon a time. After all, it looks like something a royal would have worn in the '80s... or the 1940s. As the Express pointed out, back in 1947, Queen Elizabeth II sported a yellow floral dress with puff sleeves, a cinched waist, and a bow on the neckline. Elizabeth, who was still a princess at the time, accessorized with elbow-length white gloves; Catherine accessorized with a white clutch and white pumps.

Princess Catherine wore another dress that looked quite dated during her spring 2022 Caribbean tour with Prince William. In attendance as guests of honor at a dinner hosted by the governor general of Jamaica, Catherine donned an emerald green evening gown. Between this look and the princess' aforementioned airport dress, the '80s were alive and well during this royal visit. 

Designed by Jenny Packham, the garment featured a pleated ballgown skirt and an off-shoulder neckline trimmed in voluminous organza. The bodice was adorned with sequins that rained down to the top of the skirt. While the silhouette of the dress was certainly a timeless cut — one usually cannot go wrong with an A-line gown — the ruffle detail and sparkles felt very 1980s prom. Or 1980s Academy Awards Barbie. It's a pretty dress and Catherine did indeed look like a royal, but it was not quite a fashion win for the princess.

The Prince and Princess of Wales visited the Welsh towns of Abergavenny and Blaenavon in March 2022. During the trip, Princess Catherine wore a type of shoe that was all the rage during the previous decade. While greeting well-wishers at Abergavenny Market, Catherine walked around in a pair of black suede ankle boots with a modest heel. The booties featured a metallic buckle on the outside of the ankle and a matching metal zipper on the inside. The short boots were a footwear staple for millennials in the 2010s, but this shape of ankle boot has since been left behind in favor of chunky heeled boots, sock boots, and lug-sole boots. 

Catherine further dated her look by wearing a pair of black skinny jeans. A wide-legged jean or trouser would helped freshen this ensemble up a bit, even if the princess wore the same shoes — and yes, that's only because the hem of her pants would have covered the out-of-style boots.

In 2021, Prince William created the Earthshot Prize to raise awareness of climate issues and celebrate initiatives aimed at protecting the planet. For the inaugural event, Princess Catherine wore a gown she debuted a decade prior. One of the hallmarks of the Earthshot event is that guests are expected to dress with sustainability in mind, either re-wearing garments from their wardrobe or donning a sustainably-made ensemble. Catherine chose the former, wearing a lavender Alexander McQueen gown she previously donned at the 2011 British Academy of Film and Television Arts awards. 

While she hit the mark for sustainability and nostalgia, Catherine's red carpet look didn't feel like a style win. The Grecian silhouette definitely looked every bit of its age, and her choice of a sparkly gold belt further dated the look. While some of her outfits have channeled 1980s prom vibes, this dress would have fit right in at a dance in the late 2000s. Or, you know, the 2011 BAFTAs.

Princess Catherine won't give up on skinny jeans, and she won't give up on espadrilles. During the warmer parts of the year, she's not opposed to arriving to an engagement in a pair of lace-up wedges. In June 2019, the royal attended a photography workshop for Action For Children, and she wore a pair of jute wedges for the occasion. Espadrilles are considered a European classic, but unlike many modernized styles of the shoe, Catherine's pair felt a tad too dated. The princess' warm-weather footwear featured woven soles, suede uppers and ties around the ankles, and a canvas heel and toe. Paired with her matronly patterned dress, Catherine's outfit was objectively nice, but it certainly did not scream fashion icon.

A few years later, the Princess of Wales rocked her beloved espadrilles again, and this time, she chose a dress that enhanced her look. In May 2023, Catherine attended the Chelsea Flower Show wearing the exact same pair of Castañer wedges as the ones she wore in 2019. She looked much more chic and on-trend in a Barbie-inspired dress by Me+Em, which helped to elevate the espadrilles.

In 2016, Catherine, Princess of Wales, committed a fashion faux pas that was not only outdated, but controversial. While on a ski trip in the French Alps with Prince William and their children, Catherine donned a pair of mittens that appeared to be lined with possum fur. She was slammed by PETA for wearing real fur. At the time, Mimi Bekhechi of PETA U.K. told E! News that the organization intended to reach out to the royal. "Since so many humane, warm and fashionable fabrics are readily available, there's no need to wear fur ­possum or otherwise," Bekhechi said. 

Over the last several decades, fur has fallen out of style in a major way. Since the '80s, animal rights activists, high-end fashion brands, and supermodels have taken a stand against using real fur in clothing. When Catherine sported those gloves in 2016, the fur free movement was well underway. 

To this day, this look is considered one of the most inappropriate outfits Catherine has ever worn. In February 2023, fashion expert and celebrity stylist Miranda Holder told Express, "Kate definitely made a mistake going for the possum-lined gloves, especially with society becoming more and more aware of ethical, sustainable practices. It was too controversial — and frankly old fashioned for one of the most photographed women in the world to adopt this fashion choice." As far as we can tell, the gloves never made another public appearance.