Kate Middleton's Stunning Style Transformation

After years in the spotlight, it's safe to say Kate Middleton has become one of the biggest style icons of the 21st century. From the moment she was first photographed with Prince William in that legendary red ski vest, to her stepping out in that legendary Sarah Burton gown on her wedding day, she's served up plenty of memorable fashion moments that the masses have run to replicate. But while her event style has made headlines, her everyday wear is equally worthy of attention. She's become widely known for blending the traditional with the trendy, having been spotted in midi-length dresses and blazers in a variety of colors.

Of course, as a royal family member, Middleton's style has never strayed too far from her polished and tailored wheelhouse. As José Criales-Unzueta, a contributor to British Vogue said while defining her style in 2023, "Simple, straightforward, and uncomplicated have always been the Kate signatures." But that certainly doesn't mean we haven't seen the royal mom's look blossom and evolve over time — and that includes some more casual outfits you probably wouldn't have expected to see a royal in. This style icon has gone from rocking UGG boots, to wearing some of the most elegant gowns of all time, to showing off her pantsuit passion. So grab your tiara, because we're going to look back on Kate Middleton's stunning style transformation.

Though we know her best for her dressy yet casual looks today, back in her mid-twenties, Kate Middleton was arguably even more laid back than ever. We first saw Middleton start to develop her personal style in the mid-2000s after she started dating Prince William. As royal watchers will know, the two met at college in 2001 and they started dating a year later, so Middleton seemingly knew she was going to have to dress the part in case she became a royal one day. With one exception.

Middleton famously appeared in a charity fashion show at St. Andrews University in 2002 wearing a totally sheer dress with a bandeau bra and black underwear underneath. Of course, the daring dress caused quite a stir years later when Middleton became more famous, but it seems Middleton saw the funny side of it all. Per Harper's Bazaar Australia, while attending a St. Andrews' 600th anniversary charity event over a decade later in 2012, Middleton joked to a fellow attendee, "I hope you weren't involved in the fashion show. You never know what you are going to be asked to wear!"

Sidonie Roberts, a costume designer on "The Crown" looked back at some photos of the future royal from the 2000s. She told British Vogue of Middleton's style in her early 20s, "She was capable, attractive, and never veered wildly off course. She did fashion in an acceptable way."

While young and dating Prince Harry, Kate Middleton's style was still on the more demure side — but there's no denying that in those days, she rocked a few more laid back looks that we probably  wouldn't expect to see on her today. One of her more famous casual outfits included a pair of UGG boots paired with low-rise jeans. The year was 2007, and Middleton was snapped by paparazzi rocking a cream pair of the ultra-comfortable boots with a darker wash jeans and a black belt. If that wasn't enough Y2k fashion for you, she paired it with a pink and white scoop neck, layered with a black blazer over the top. Ah, 2000s style. The future royal then accessorized with a white bag and statement white necklace. Clearly, this star has always had an eye on what's hot, because there's no doubting UGGs were the hot shoe trend at the time — but we're guessing she probably doesn't still have this outfit in her wardrobe today.

Middleton also expressed herself through some less than royal approved Halloween and party costumes at the same time. In 2007, she was spotted in a super short witch costume with black knee-high boots and a cape. The following year, she attended a costume party wearing a green sequin halterneck with yellow short shorts. 

In early 2007, Kate Middleton and Prince William briefly split up. They reconciled just a few months later that summer, and, around that time, we started to see an even more style-conscious Middleton. Per Glamour UK, Middleton's style was decidedly more feminine and trendy, marked by handkerchief hems, paisley patterned everything, lacey dresses, and above-the-knee hemlines. 

As the world started to take even more notice of the future royal's style with their split and reconciliation (hey, the course of true love never did run smooth), some royal experts believe Middleton may have been reflecting a change in her clothing.

While Middleton didn't speak openly to the press about the split, or anything else for that matter, royal experts certainly had a lot to say about her developing style. Tina Brown wrote in her book, "Inside the House of Windsor — The Truth and the Turmoil," that Middleton appeared to use her style as a way of letting the world know what she was thinking without having to talk to reporters, all while cementing herself as a relatable woman. "Rarely dressed in anything that the British public couldn't afford, she presented as the perfectly pitched girlfriend from the manor next door in fresh, swingy high street dresses [and] cropped blazers," she wrote. "She became a mute icon of appropriate style." And we certainly saw that when Middleton was snapped alongside her then boyfriend at The Cheltenham Gold Cup Festival 2007 wearing a paisley scarf, beret, and gray jacket.

Following her reconciliation with Prince William, people started taking even more notice of Middleton's fashion choices. And the fact that her style appeared so achievable seemed to only work in her favor. "Her personal style was attainable and relatable, it was easy to replicate, and dressing like her was not necessarily a daunting task," José Criales-Unzueta, a contributor to British Vogue, said of her looks.

In 2008, Middleton started to become more entwined with the royal family and even got assigned her own security detail – which also appeared to come with a wardrobe change fit for a royal. She began to develop a love for the brand Issa, which is when we first started seeing the more modern yet sophisticated side of Middleton come out. She attended the Boodles Boxing Ball wearing a mixture of high-end and more affordable pieces. The look included a satin Issa gown, a clutch from British department store John Lewis, Tiffany & Co. earrings, and Prada pumps. 

But it wasn't all quite so timeless when it came to Middleton's wardrobe. The then future royal also wore some bolder prints, something we don't see a lot from her these days. She was also papped in 2008 in a bold multicolored shift dress, which she accessorized with a black waist belt.

In 2010, Kate Middleton and Prince William announced their engagement and the world saw an even more glamorous side of the prince's bride to be. But that didn't mean she was about to ditch somewhat more affordable fashion for thousand dollar gowns all the time. Middleton wore one of her most famous dresses ever when she and her royal husband-to-be spoke to the press about their big news, a navy blue Issa wrap dress. 

The dress was priced at £385 (around $490) — and the world certainly paid attention to this sophisticated royal style we were seeing from the future Princess of Wales. The dress had people across the globe clamoring to get their hands on it, with plenty of replicas popping up online. "Since the announcement of the royal engagement we have been inundated with requests regarding Issa. The dress worn by Kate sold out almost immediately," Harvey Nichols' buying director Averyl Oates told British Vogue.

Issa's founder and former creative director Daniella Helayel revealed just how big Middleton wearing the dress was for her brand. "Issa was a niche brand; we had a loyal following, but in 2008 and 2009 we were in serious financial trouble. When Kate wore that dress everything changed," she told Daily Mail. But, even though Issa's sales doubled thanks to Middleton, Helayel and her team just couldn't keep up with demand and the brand Issa became no more.

Kate Middleton pulled out all the stops when she married Prince William in 2011. Her stunning one-of-a-kind wedding gown was designed by Alexander McQueen's Sarah Burton — all under Middleton's instruction, of course. In a statement, the royals explained why Middleton chose the gown and designer. "Miss Middleton wished for her dress to combine tradition and modernity with the artistic vision that characterizes Alexander McQueen's work," they said.

The royals also shared the inspiration behind the gown, which featured ornate lace sleeves and a nine-foot train. "The dress epitomizes timeless British craftsmanship by drawing together talented and skilled workmanship from across the United Kingdom. The dress design pays tribute to the Arts and Crafts tradition, which advocated truth to materials and traditional craftsmanship using simple forms and often Romantic styles of decoration," the statement read. "Ms Burton's design draws on this heritage, additionally giving the cut and the intricate embellishment a distinctive, contemporary and feminine character." Just like Middleton herself.

Of course, the dress cemented its place in fashion history and even inspired a change in the bridal industry. "As Kate stepped out of the car to reveal her dress, a BBC pundit practically squealed, 'This is such a fashion moment!' And it really was. Naughties bridal boutiques were packed with huge tulle ballgowns and you'd be lucky to have found a strap, let alone a sleeve [before Middleton]," designer and dressmaker Holly Winter told HuffPost UK.

After marrying Prince William, Kate Middleton's style developed into outfits that were more practical, with slightly longer hemlines, perfect tailoring and neat edges. And Sarah Harris, deputy editor and fashion features director at British Vogue, claimed that was very much intentional from the new official royal. "Working royals endure long days and so the clothes have to work, from being comfortable, to weather appropriate, to magically immune to wrinkling," Harris shared. "Nothing can be too fussy, so forget a slit that's tricky to navigate, or a collar that needs tending to."

Middleton proved that in 2011 when she showed off a stunning royal appropriate wardrobe during an official visit to Canada. She opted for plenty of classic yet stylish outfits during the trip, including wearing a navy Roland Mouret cut to the knee dress with a matching blazer, as well as a stunning royal blue lace topped dress by Erdem. All with an array of sensible court shoes (with are a modern royal's staple, of course).

It was around this time as an official working royal when Middleton really began to cement the style we've come to associate with her today. Classic silhouettes presented in a classy, sophisticated, and feminine way. "Kate is very much a classic style personality where we see her in more traditional heritage styles and prints," style expert Lisa Talbot told Mail Online. "This is her signature style that she has created."

All eyes were on Kate Middleton when she fell pregnant with her first child in 2012. And she showed the world how to be classy and elegant while expecting. Middleton quickly developed her own style around her expanding bump, as she opted a lot for bump skimming outfits. Middleton appeared to be a fan of designer numbers throughout her first pregnancy (and the two that followed), as the was spotted in likes of Seraphine, Tory Burch and Alexander McQueen.

The royal wore plenty of button-down coats and shift dresses, which gave her bump room to grow without making it the focus of her outfit. Four months after announcing her pregnancy, she stepped out in an Erdem shift dress, and who could forget the blue and white polka dot Jenny Packham dress she wore when Prince George met the world for the first time in 2013? That dress stayed true to her classy, elegant style, but bucked her maternity trend somewhat as it cinched at the waist.

Rosie Pope, founder of Rosie Pope Maternity and Rosie Pope Baby, took note of Middleton opting for a higher, scooped neckline during her first pregnancy. Naming the look "The Princess Kate", Pope told ABC News, "Kate is rather conservative and her style reflects that but this is what works for her, it makes her comfortable. She is spot-on for her body, her comfort level and the elegance of a royal."

Though it's long been considered a fashion no-no to re-wear the same outfit twice as a celebrity, Kate Middleton has proved time and time again that she's not a believer in all that. As a working royal, she's re-worn countless outfits over the years, and really seemed to step up her re-wear game after she became a mom. One of her most famous re-wears has to be the stunning dark teal Jenny Packham gown she wore twice in 2014, once at the Portrait Gallery Gala and then again while attending a dinner in New York.

And Middleton has received high-praise for her outfit repeating, as well as for leaning towards labels who are dedicated to more sustainable manufacturing. "Considering the impact that Kate Middleton's fashion choices have across the world and what Kate wears sells out the minute she's seen wearing it, it's only a good thing that she's throwing her support by wearing more eco-friendly and ethical labels ... proving she has a key role when it comes to being involved in sustainable fashion," celebrity stylist Lalla Bronshtein told Express.

Around this time is when we also saw Middleton getting extra glam via the royals' jewelry collection. In 2015, she wore the Lover's Knot Tiara, a gift to Princess Diana from Queen Elizabeth II. The following year, we saw her start wearing a number of the late queen's other pieces, including earrings.

After years of wearing dresses and skirts to royal events, in 2023, Kate Middleton appeared to develop more of a penchant for pantsuits. The royal was spotted wearing multiple matching pants and jackets at different events. Among them, a dark green Burberry two-piece during a royal visit in the UK, while she opted for an all-white two-piece look while attending the Rugby World Cup in France.

At the time, style experts suggested the future princess may have been evolving her style following the death of Queen Elizabeth II. After the late queen's passing, Middleton and Prince Harry were given the title of Catherine, Princess of Wales, and William, Prince of Wales as they moved up in the line of succession. "As we are now firmly in the king's reign, Catherine is now starting to establish herself in her new role as Princess of Wales," Royal historian Jessica Storoschuk explained of the fashion change to Page Six.

Bethan Holt, fashion director at the Daily Telegraph, also dished on her decision to wear so many pantsuits throughout 2023, telling People, "Her trouser suits could be seen as a visual cue of her professional approach to her new position in the family. I think this is her power moment — she's easing into the Princess of Wales role and that promotion that she's had in such a beautiful way. She's got this big new title, and she's dressing for that job."

Going into 2024, Kate Middleton is expected to be in the spotlight just as much as she always has been. And that could mean we see her style evolve even more. According to Mirror, Kate Middleton and Prince William are expected to head overseas to visit the British Armed Forces, so it'll be interesting to see if Middleton continues with her pantsuit love or makes the move back to dresses and skirts — or tries a new look entirely.

But, whatever she decides to do next, we'd bet it's going to be something elegant and classy in keeping with the chic style she's carved out for herself over the years. "Not much has changed, other than the fact that she's grown up and now dresses for the job she has," José Criales-Unzueta told British Vogue of Middleton's style transformation over the years. "The suits, the coat dresses — they're all an extension of the same normalcy," he said.

Middleton proved that on Christmas Day 2023 when she appeared to give us a taste of how her style will always true to her classy and elegant core. As the year drew to a close, she stepped out with her family in a tailored royal blue coat (Middleton is clear a fan of the shade) with a navy turtleneck, matching boots, and a fascinator.