Throwback Pics Of Kate Middleton Prove We Don't Talk About Her Iconic 2000s Style Enough

After tying the knot with William, Prince of Wales, in April 2011, the style icon that is Catherine, Princess of Wales, was born. Her wardrobe is full of regal pieces, from monochromatic suits to banquet-ready ballgowns, and all of them are worlds away from the looks she used to rock back in the 2000s, when she was just dating William.

"Since Kate has been in the limelight she has always been somewhat of a conservative dresser, whether that was because she wanted to prove herself to the Royal Family or was her own personal style, who knows, but she was rarely seen in anything too risqué," celebrity stylist Anthony McGrath told Express in 2020. "However, since marrying Prince William and officially becoming a member of the Royal Family, her outfits have certainly become more modest ... She had to leave behind the flirty and floaty dress, thigh-skimming minis and low-cut evening gowns."

Looking back at Kate's pre-royal style, it's clear she mastered the fashionable London look by embracing Princess Diana's signature Sloane Ranger image, which was an amalgamation of stylish Chelsea trends and upper-class English country. But she also rocked plenty of Y2K crazes that every other millennial took under their wing, from low-rise jeans to slouchy bags. Many of her most iconic noughties fashion moments took place at polo matches, where she delivered equestrian-chic looks. But there were also lots of 'fits that showed off her playful, carefree style, which tends to be rare in her post-royal rotations.

If there's one garment that can sum up Kate Middleton's 2000s style better than the rest, it's low-rise denim, which staged a comeback in 2023. Hip huggers were a staple of the early aughts, but even by June 2005, when the future Princess of Wales was snapped with her father Michael Middleton in the Scottish town of St. Andrews, high-waisted jeans were yet to rise to popularity. Kate paired her light-wash jeans with a crochet-style black belt — another go-to accessory for her during this era — and a simple lace-trimmed white cami with spaghetti straps.

From fascinators to tiaras, Kate Middleton wears many things on her head these days, but we aren't expecting to see a cowgirl hat anytime soon. Back in August 2005, Kate attended the Festival of British Eventing at Gatcombe Park dressed in a Western-inspired 'fit. Wearing slim-fitting jeans and a chocolate jacket, she accessorized with a matching suede bag, knee-high boots, and a brown cowgirl hat. Quite the departure from her regal wardrobe today, this country-leaning ensemble seemed to be an edgy take on the Sloane Ranger aesthetic that many British royals and aristocrats have embraced over the years. 

Even before officially marrying into the royal family in April 2011, Kate Middleton was mixing with British high society. In June 2005, she attended the wedding of Hugh Van Cutsem and Rose Astor in Burford, England, and her getup offered a preview into her future princess style. She went for a sophisticated black-and-white look, pairing a lacy knee-length pencil skirt with a white blazer and a black fascinator. As a royal, Kate Middleton tends to favor monochrome (in a possible nod to Queen Elizabeth) rather than color-blocking like this, but the formal 'fit definitely gave us a glimpse into what was to come. 

At the complete opposite end of the spectrum, one of the Princess of Wales' most iconic noughties looks was the retro ensemble she put together for a charity roller disco in September 2008, prior to her engagement to William, Prince of Wales. Rocking a sea-green sequined halter top — wrapped with a bow, no less — the future royal finished the look with yellow short-shorts, knee-high boots, and bubblegum-pink leg warmers. This lewk might not have been indicative of her Sloane Ranger aesthetic overall, but it was absolutely a standout moment in the stunning style transformation of Kate Middleton.

Attending polo matches is part of the deal when you're dating a British prince, and Kate Middleton often embraced a country-chic vibe when she did during the noughties. But she ditched the Sloaney boots and jackets for a feminine sundress (one of the kinds of dresses that everyone should own) at the Chakravarty Cup in June 2006. The red polka-dot number featured a low V-neck and A-line bottom, and she paired the look with red strappy sandals. While the carefree 'fit wasn't quite horse-ready, it foreshadowed the many frocks Kate would wear once she moved into Kensington Palace.

Made famous by Princess Diana, the Sloane Ranger aesthetic is the quintessentially British version of old money, the classic fashion trend which got a modern comeback in 2023. Combining upper-class equestrian staples with designer knitwear and other preppy touches, this is the top style you'll find on the side of a polo field, and Kate Middleton understood the assignment. For the Badminton Horse Trials in May 2007, she wore a navy knit with her shirt collar sitting on top, a white skirt, her go-to knee-high boots, and a tan belt. Talk about country chic!

Kate Middleton's noughties style featured elements that clearly placed her in the British upper crust, but she also embraced contemporary trends, too. While attending the Dorchester Trophy polo match in June 2009, she went for dark-wash skinny jeans, which were a staple of the coming decade and had already started to dominate trends by 2008. She paired her denim with a cute "going out" top — another millennial mainstay — wedges, and a slouchy handbag that screamed Y2K. Kate Middleton also appeared to wear her hair in natural waves, which gave the look a laid-back vibe.

Kate Middleton (and the rest of the world) was yet to embrace the skinny jean trend in 2006. That July, she attended a match at the Beaufort Polo Club with Chelsy Davy, who was dating Prince Harry, Duke of Sussex, at the time. While Davy's aesthetic was Y2K boho, Kate's was straight Y2K, with low-rise straight (but not skinny) denim and a sheer cardigan. Regardless of the year, the white jeans were a perfect choice for summer. Of course, you don't have to wait until Memorial Day to embrace white denim!

In April 2007, the Prince and Princess of Wales, then Kate Middleton and Prince William, called it quits. That February, it seems Kate was already living it up when she was snapped in a taxi on her way to Mahiki Club in London. For the night out, she donned a gray-and-yellow silky dress with an empire waist and spaghetti straps. While this was a standard noughties silhouette, the frock is unforgettable, even to this day, for being so different from the wardrobe we've come to associate with the royal.

If there's one thing we never thought we'd see, it's Kate Middleton rocking Ugg boots. But back in May 2007, she was photographed on the streets of London wearing a pair of the comfy shoes to finish off her outfit, which featured low-rise medium-wash jeans, a pink-and-white cami, a black jacket, a statement necklace, and once again, a buckled belt. In Kate's defense, A-listers were also donning the sheepskin boots throughout the noughties, so what looks like an overly relaxed 'fit by current standards might have been an example of the princess' innate fashion prowess.