Kate Middleton's Most Underappreciated Looks

Catherine, Princess of Wales is an undeniable trend setter. She has such power over the clothing economy that her influence has been dubbed "the Kate effect" to capture how much onlookers attend to what she wears. However, on occasion, Catherine has stepped out in something daring and dazzling, but the look has gone underappreciated. So, our interest here is to examine Catherine's outfits that were met with ambivalence when they were really fabulous. In more extreme cases, these outfits were actually roasted on social media. In other, less extreme cases, the looks were treated as filler wardrobe and not something truly remarkable. But over time, they've aged into meaningful looks. 

In all of these cases, Catherine was doing something unique; she was stepping out of her typical style and opting for a more daring silhouette. In those moments, fans either disliked the outfit entirely, or forgot about it entirely. So, we're here to revive those forgotten looks and praise the boldness of others that were derided. Note that famous outfits like Kate Middleton's gold gown from the James Bond "No Time To Die" premiere did not make the list. She positively sparkled in her Jenny Packham number, and many suspected that Kate secretly underwent a hair and makeup makeover because her look that night was so dazzling. Instead, this list explores moments when Catherine stepped out of her comfort zone and delivered something interesting that people didn't respond to in the ways that they should have.

While dark jeans and a cowboy hat aren't typically what one thinks of when it comes to the royals, Catherine, Princess of Wales once donned this exact look. Granted, she was dressing for the location, so one could argue that she was being a polite guest. In July 2011, only months after her wedding to Prince William, the couple attended the Calgary Stampede while visiting Canada. Since the event is a rodeo in celebration of Calgary's western heritage, it was fitting that Catherine and William wore the garb associated with this popular Canadian celebration. At the time, Catherine's on-theme outfit was brushed off as simply dressing for the region, but her cowgirl look has stood the test of time. 

For one thing, Catherine made the western outfit look so chic. She wore a sheer, lace blouse with dark bootcut jeans and brown suede cowboy boots, along with a turquoise belt and a white cowboy hat. Secondly, it showed a respectful level of engagement with the country and their traditions, even though it was out of their typical styles. Prince William joked about it in a speech, saying, "Well, this is different," as he tipped his matching cowboy hat (via CBS News). Finally, we've never seen Catherine dress like this since, so the cowgirl look was really a special moment in her evolving wardrobe history. It may well be a once-in-a-lifetime moment.

Fashion cycles through phases, and Catherine, Princess of Wales, tested a style that had clear historic roots, but it was one that many people weren't ready for. In May 2021, she visited the V&A Museum in London wearing a red and black Alessandra Rich dress with long sleeves, a Peter Pan collar, puffed sleeves, and a drop-waist skirt. While the dress itself was new, the drop-waist silhouette harks back to the 1920s, when the Flapper Era saw an increase in drop-waist dresses, and again in the 1960s, when the Mod Style saw a resurgence of low-waisted dresses. 

Catherine modernized this retro look by wearing navy Jennifer Chamandi heels, a matching clutch, and pair of dainty gold hoops. Despite her attempts at making the red houndstooth dress approachable for contemporary audiences, people weren't into it at the time. In a post on X showing a range of Catherine's favorite Alessandra Rich dresses, someone asked, "Kate's Alessandra Rich dresses. Which one do you like the most?" The collection of photos included this red number. "None of them, God please no more low-waisted [Alessandra Rich] dresses," an X user tweeted, referring to the designer. "None of them, unfortunately. She's beautiful ... this style is too dowdy for her," another X user responded. The underappreciated style ended up creating a new trend, however. The drop-waist dress made a huge comeback in 2025, with major fashion and lifestyle publications waxing poetic over its whimsical, retro charm. Catherine's always a trend-setter. 

While we know that Catherine, Princess of Wales, loves her coats, she did something unique at a private screening for "Cruella" in May 2021. During the COVID-19 pandemic, Catherine organized a drive-in screening of the film for healthcare workers at the Palace of Holyroodhouse in Edinburgh, Scotland. For the occasion, Catherine wore a blue, plaid trench coat by Holland Cooper, and paired the ankle-length outerwear piece with green suede heels. She slicked her hair up in a ponytail — a rare hairstyle for the princess — and accessorized with sapphire and diamond earrings. The earrings once belonged to Princess Diana and, thus, were borrowed from the late Queen Elizabeth II for the Holyroodhouse screening.

While coats and coat dresses are nothing new for Catherine, the ensemble at this event was unique in that her outerwear is typically more subdued with a single tone. This style moment was different; the coat was dramatically long, for one, and also daringly embellished with gold hardware and a wide buckle strap with edgy rivets. It was a change from her usual coat choices and, sure enough, there were people who didn't see its magic at the time. "Sorry, I don't like it," someone commented on an Instagram post about Catherine's style. Of course, there's always a small group of people that don't understand why Catherine sometimes opts for these bolder choices. And, as with the other outfits of hers that went underappreciated at the time, the plaid coat has stood the test of time. We'd love to see her wear it again.

Catherine, Princess of Wales championed a good cause while making subtle but marked changes to her wardrobe. In October 2021, Catherine spoke at the Forward Trust's "Taking Action on Addiction" event in London to address misconceptions around addiction. She arrived in a very unique outfit that wasn't fully appreciated at the time, largely because it was a daytime event — as opposed to a red carpet — and wasn't quite as dramatic as the ensemble she put together. 

Catherine wowed in a monochromatic red look with a turtleneck from Ralph Lauren and a long, pleated skirt by Christopher Kane. She accessorized with a warm, caramel brown tone that perfectly offset the acidic red and matched her butterscotch brunette locks. Catherine also kept it youthful and sexy by wearing a fitted top with the ample skirt. The bold red look was actually a major moment in Catherine's sartorial life; her style had notably changed. For instance, in her early days as a royal, Catherine was partial to shorter dresses and skirts. As she climbed the ranks, becoming more essential to the monarchy, her hemlines lengthened. It had everything to do with being such a senior member in the royal family, and Catherine used her wardrobe to signal this elevated status. The reason this red outfit from 2021 is so special in hindsight is that the hemline is so exaggeratedly long — one of the longest we've ever seen on her — as if she's dramatically preparing fans for the new change. It was the dawning of a new silhouette for the princess.

Yikes. Catherine, Princess of Wales, got absolutely roasted for wearing a yellow Alessandra Rich dress at the Lynden Pindling International Airport when she and Prince William visited the Caribbean in March 2022. The look undeniably harked back to the '80s, with its exaggerated shoulders, the bow at the neckline, and the bedazzled belt buckle. She styled the bold jacquard peplum dress with white heels and a white clutch. Unfortunately, the outfit was completely rebuked at the time by fashion fans. It made its way onto a list of Catherine's most surprisingly outdated looks, and folks online could not stop chiding her for it. 

One user on X compiled a grouping of all of the Alessandra Rich dresses that Catherine had worn, and the yellow one garnered a lot of negative feedback. "The yellow one was really dowdy/old-fashioned looking," a netizen quipped on X. "The yellow one is a big no-no for me I'm afraid, very '80s," another X user tweeted. However, the fact that the yellow dress didn't look like something Catherine would typically wear was the whole point. She was trying something bold and new, departing from her usual style, and such a daring choice by a royal figure is worthy of respect.

Catherine, Princess of Wales, completely nailed her red carpet look at the London premiere of "Top Gun: Maverick" on May 19, 2022. She wore the Lamble Off-The Shoulder Two-Tone gown by Roland Mouret, which featured an elegant black panel and a white band around her chest. She paired the dress with Tsar Star Studs and Drops earrings by Robinson Pelham, which cost over $14,000. Her choice of outfit that night was a remarkable one; since the fitted black gown was relatively simple, it went largely unnoticed and was quickly eclipsed by her history of other, more lavish premiere looks. Think of that gold Jenny Packham gown she wore in 2021 to "No Time To Die." But the black Roland Mouret gown was a big moment in her sartorial portfolio; it marked Catherine's turn toward more modern silhouettes. It was far more daring — with the exposed shoulders and form-fitting fabric — than many of her other gowns. She looked every bit like the modern princess, embracing bodycon dresses that still looked classical. 

While the dress was underappreciated at the time, the presence of both Catherine and William, Prince of Wales, was still a huge success at the event. Catherine and Prince William had several Hollywood A-listers swooning at the premiere, particularly Tom Cruise, who couldn't stop doting on the chic royals. And it's no wonder. William looked dapper in velvet, while Catherine captured the perfect outfit for a modern red carpet.

Catherine, Princess of Wales, served up one of her most interesting Commonwealth Service looks in March 2023. In years past, her outfits weren't always this exciting. For reference, in 2025, she arrived in a head-to-toe red ensemble, sporting a midi coat dress with an oversized bow by Catherine Walker. In 2022, she arrived in a monotone midi coat dress in blue, also by Catherine Walker. In 2020, she wore a different red coat dress by Catherine Walker. The point is, it feels like Catherine goes for a primary color for the Commonwealth Service and makes her outfit monochromatic. She almost always opts for a coat dress; this garment is so ubiquitous it's been included in the list of clothing items that Catherine can't live without. While she always looks good, it can get a little tedious after a while.

This is why her 2023 Commonwealth Service outfit was such a special thing, and yet it went largely unnoticed at the time. Instead of a coat dress in a single color, Catherine wore a skirt suit by Erdem that wasn't even available for purchase by regular folk until months later. The jacquard print was flirtatious and festive; both the skirt and jacket featured a peplum flare, and she donned it with a wide navy hat. It was absolute perfection and undoubtedly will go down in history as one of her best looks for the Commonwealth Service.

Catherine, Princess of Wales, chose the 2023 Trooping the Color as a way to support her husband, William, Prince of Wales. She wore an emerald green dress by Singaporean designer Andrew Gn, a brand she had never worn before. The choice of dress was in honor of William's Earthshot Prize ceremony, which was to be held later that year in Singapore, so her collaboration with a designer from that country was a lovely, intimate gesture. Fans will recall that Catherine wore another vibrant green dress in Boston for the 2022 Earthshot Prize awards in Boston. It's a hue often associated with her support of William. 

The dress was unlike any other we've seen on Catherine for Trooping the Color. In years prior, Catherine almost always opted for a pastel-toned coat dress that cut off around the knee with fussy little fascinators. But in 2023 — her first year as the Princess of Wales following the death of Queen Elizabeth II — Catherine blew the doors out with the vivacious dress by Gn, along with a wide-brimmed hat by Philip Treacy. It was a fabulous and unique look, one that looked fresh and new for the princess. While the look went underappreciated at the time, there were a few who understood the significance of Catherine's new role and new style. "She's taking on the queen's vibrant style and making it her own," a user commented on Instagram. As Catherine gets closer to the crown, she's taking the late Queen Elizabeth II's lead on wearing bright colors.

The year 2023 marked a major style transformation for Catherine, Princess of Wales in regards to her Wimbledon attire. She was levelling up. Prior to this time, Catherine arrived in unimaginative, knee-length dresses. For instance, from 2014 until 2018, Catherine arrived in tea dresses in a variety of prints, but they were nothing special. In 2022, Catherine lengthened her hem and finally opted for more interesting choices. The next year, things got even better. Her series of 2023 Wimbledon looks, crowned by the charming green skirt suit, was a new era of style for her at the matches. She was bringing a more sophisticated aura to the games; the blazer and midi skirt would become her new, go-to look at Wimbledon. It also proved inspirational for many, as the midi skirt is trending again, thanks to people seeing how good it looked on the princess. In 2025, midi skirts then exploded, which is on par with Catherine's trend-setting effect on fashion. 

While the impact of this new style upgrade would become evident over the next few years, the tennis ball green outfit was appreciated even then. The Wimbledon 'fit was included in Kate Middleton's best looks of 2023, so people appreciated it. However, there was still a percentage of the population that missed the charm. "Am I the only one who doesn't like this look? Feels like top and bottom belong to different outfits," one Instagram user commented. They'd catch on soon enough.

There was one outfit that Catherine, Princess of Wales wore that went largely unnoticed until people picked up on the sweet, nostalgic element of it. In February 2025, Catherine and William, Prince of Wales, visited the Meadow Street Community Garden and Woodland in south Wales. For the outdoor occasion, she wore a very earth-toned outfit. She paired a plaid, pleated skirt with a turtleneck, brown boots, and an olive tweed jacket. She accessorized with a bright yellow floral pin.

Internet sleuths made an incredible discovery; the jacket that Catherine wore in 2025 was the very same one she wore way back in 2007, when she attended the Cheltenham Horse Racing Festival with William years before they married. According to People, the nearly 20-year-old jacket is by Ralph Lauren, and Catherine originally wore it with a matching skirt and a blue button-down shirt. So, the magnitude of her look in February 2025 was almost completely missed. What appeared to be a simple, cozy outfit on first glance was actually a great example of sustainable royal dressing. Just because something is nearly two decades old doesn't mean it's rubbish. We wonder what else Catherine will bring back from her pre-wedding wardrobe. 

French president Emmanuel Macron and his wife, Brigitte, visited London in July 2025 on an official state visit. For such an important event — and a diplomatic one at that — even clothing becomes symbolic. So, it was a major moment when Catherine, Princess of Wales, greeted the French couple wearing a quintessentially French designer: Christian Dior. She wore the 2024 Dior 30 Montaigne Rose Des Vents Bar jacket with a midi tulle skirt and a jaunty hat by Jess Collett in similar tones. Many initially missed its petal pink charm, as is typical of these unappreciated outfits of hers. "Seriously in need of a fashion update, definitely granny vibes going on with her look constantly," one user commented on Vogue's Instagram post about Catherine's Dior outfit. "I don't see a tulle skirt as an appropriate choice for a diplomatic occasion," another Instagram user wrote.

Those who derided Catherine's choice completely missed the point. It was the first time that Catherine wore Dior, and the fact that an English princess greeted the French president in a designer from his country was thoughtfully diplomatic. The romantic ballet-inspired outfit paid homage to France, and it was a gesture of peace and welcome to Macron. Rather than wearing a color typically associated with France, Catherine paid homage to the art and beauty of the country.