Celeb Style
Kate Middleton wearing a diamond tiara as part of Kate Middleton's fashion evolution at Buckingham P...

Kate Middleton’s Fashion Evolution Goes From Flirty To Royalty

She’s been serving looks since the early aughts.

WPA Pool/Getty Images Entertainment/Getty Images

Kate Middleton’s evolution from university student to working girl to Duchess of Cambridge and then Princess of Wales has been a thing of beauty. As the future queen’s influence and prestige have grown, so has her sense of style. While she’s always known how to put a ’fit together, Middleton has experienced quite the fashion evolution since she first stepped into the public eye in the early ’00s.

When Princess Kate and Prince William began their relationship in 2001, Middleton’s looks were the physical embodiment of Y2K fashion. From low-rise denim and sequined halter tops to Parisian berets and leg warmers, the future royal’s outfits were eccentric, fun, and reflective of the time period.

Post-uni, Middleton became best known for her polished sets and formal fascinators, but it wasn’t until she officially became a member of the royal family that the princess’s style became synonymous with elegance. You could say that royal fashion protocol has played a role in shaping her tastes, but Middleton’s style has more depth than a pastel two-piece and matching hat. In fact, the Princess of Wales has managed to elevate her personal tastes to the exacting level of royal fashion expectations.

From vintage looks inspired by her late mother-in-law, Princess Diana, herself a major fashion icon, to modern monochromatic moments, Middleton has created a royal wardrobe that’s all her own. From her university days to now, here’s a look at how Kate Middleton’s fashion has evolved over the past two decades as seen through some of her most iconic fashion moments.

2005: Kate Middleton In Western Wear

Max Mumby/Indigo/Getty Images Entertainment/Getty Images

The Princess of Wales was wearing western fashion long before it made its recent comeback. At an outdoor event in August 2005, Middleton arrived in an outfit rivaling that of Indiana Jones. Dressed in a tan cowboy hat, suede jacket, light wash denim jeans, and dark brown riding boots, Middleton looked ready to wrangle a steer or rescue an artifact.

2005: Kate Middleton’s Dark Academia Era

Anwar Hussein Collection/ROTA/WireImage/Getty Images

Say hello to the perfect mix of posh and prep. At her St. Andrews graduation in June 2005, Middleton managed to make her university gown look unbelievably sophisticated. With a crisp white blouse, black pencil skirt, sleek kitten heels, and a boho brown bag, the university graduate was serving major Gossip Girl energy.

2006: Kate Middleton’s Boots With the Fur

Tim Graham/Tim Graham Photo Library/Getty Images

Donning a Siberian-style fur hat, tailored cream trench coat, and slouchy brown boots, the princess arrived at the ’06 Cheltenham Festival looking fabulous in this cozy, military-inspired ensemble. Middleton’s outfit was the perfect combination of smooth lines and soft accessories.

2006: Kate Middleton’s Feather-Forward Fascinator

Mark Cuthbert/UK Press/Getty Images

If there’s one thing Kate Middleton can do, it’s put together a show-stopping wedding ensemble. At Laura Parker-Bowles and Harry Lopes’ wedding in May 2006, Middleton arrived in a lovely ivory brocade coat, cream-colored pumps, and a statement fascinator with brown feather detailing.

2007: Kate Middleton In Chocolate Brown

Mark Cuthbert/UK Press/Getty Images

The Princess of Wales combined a number of Y2K fashion staples in this ’fit from 2007. The combination of robin’s egg blue blazer, chocolate-colored midi skirt, brown stiletto boots, espresso brown beret, and paisley scarf have big ’00s energy. It’s worth noting that this is one of the last times Middleton mixed different shades of the same color. As a full-time working royal, she would eventually stick to monochromatic or perfectly matched outfits.

2008: Kate Middleton’s Disco Queen Moment

Max Mumby/Indigo/Getty Images Entertainment/Getty Images

Dancing queen, young and sweet, only... 26? At her roller disco-themed birthday party in 2008, Middleton’s party ensemble turned heads. Wearing a sequined teal halter top, bright yellow hot pants, bubblegum pink leg warmers, and black knee-high boots, the future duchess was all smiles.

2011: Kate Middleton’s Pastel Princess Moment

Pool/Getty Images Entertainment/Getty Images

At the BAFTA Brits to Watch Gala at the Belasco in Los Angeles in 2011, Middleton stole the show in a powdery lilac Alexander McQueen floor-length gown. Cinched at the waist with a shimmering ivory belt, this gown marked the princess’s shift into a decidedly more sophisticated style direction.

2016: Kate Middleton’s Off-The-Shoulder Elegance

WPA Pool/Getty Images Entertainment/Getty Images

Understated and elegant, this stunning Barbara Casasola dress is one of Middleton’s most iconic pieces to date. In fact, this silhouette has become one of the princess’s go-tos. She seemed to especially love this piece as she’s worn it twice to major functions. The ribbed off-the-shoulder dress made its first appearance in 2016 and was spotted once again in 2019.

2016: Kate Middleton Ups Her Fashion Game

Samir Hussein/WireImage/Getty Images

This Tory Burch maxi dress was one of Middleton’s most unexpected looks, but truly one of her best. Worn to a dinner with the king and queen of Bhutan in April 2016, this dress features both colors and textures, including chained beaded details, that were a step outside of the princess’s comfort zone. Paired with a burnt sienna shawl and gold statement earrings, the gown took Middleton from British to bohemian royalty.

2019: Kate Middleton In Wide-Leg Trousers

WPA Pool/Getty Images Entertainment/Getty Images

Leave it to Kate Middleton to turn a trip to the museum into a runway walk. In October 2019, Middleton arrived at the Natural History Museum in London wearing this fantastic fall ’fit. The tones of forest green and plum were warmed by her gold jewelry and quilted Chanel purse for a look that was the epitome of autumn.

2020: Kate Middleton In Glittering Green

Chris Jackson/Chris Jackson Collection/Getty Images

In a dazzling emerald midi dress by the Vampire’s Wife, Middleton paid homage to Ireland and its iconic beer at the Guinness Storehouse Gravity Bar during a royal tour in March 2020. With a gorgeous gold clutch and sleek velvet green pumps to match, the former Duchess of Cambridge stunned with this glamorous look.

2020: Kate Middleton In Beige & Tartan

Chris Jackson/Chris Jackson Collection/Getty Images

During her tour of Scotland with Prince William in May 2021, Middleton made heads turn with this tasteful, tailored look. Featuring a structured camel coat, beige trousers, matching tan pumps and handbag, delicate gold jewelry, and a tartan scarf to tie everything together, the duchess sure knew how to make an entrance at the grand opening of a hospital in Orkney.

2021: Kate Middleton In Red & Pleats

Karwai Tang/WireImage/Getty Images

Middleton was the definition of ravishing in this scarlet number at the Taking Action on Addiction campaign in October 2021. With a fiery red turtleneck sweater and long pleated skirt to match, Middleton paired the bold monochromatic ensemble with brown Ralph Lauren pumps and a beautiful toffee-colored micro-bag from DeMellier.

2022: Kate Middleton Wears Green In Jamaica

Samir Hussein/WireImage/Getty Images

The princess looked positively exquisite in this dark green gown created by British designer Jenny Packham. Worn to a state dinner in Kingston, Jamaica, during a royal tour in March, Middleton was the picture of regality in this piece. With its ruffled off-the-shoulder neckline, cascading tulle skirt, and glittery details, this is undoubtedly one of her best dresses.

After nearly two decades of being blessed with Kate Middleton’s fashion sense, can it get any better?