
Kate catches William’s eye
Kate Middleton first became friends with Prince William in 2001 while they were both students at University of Saint Andrews, but as the story goes, the young prince first realized he was attracted to Kate when she modelled this transparent dress by designer Charlotte Todd at a charity fashion show for the school. That was in March of 2002. The two didn’t become an “item” until late 2003, however, and she wasn’t photographed regularly by the media until 2004.

William’s girlfriend, Kate Middleton
In March 2004, Prince William and Kate Middleton went public with their romantic relationship (while skiing in Switzerland). In the early months of the relationship, Kate’s style was still that of a “typical college girl.” Here, she’s wearing a white “Wild Thing” t-shirt with a tight, low-slung thigh-grazing skirt, wide belt, and knee-high boots by designer Penelope Chilvers.

Two weddings
Here, Kate is seen attending the June 5, 2005 wedding of Hugh Van Cutsem and Rose Astor, at which her then-boyfriend, Prince William, is an usher in the wedding party. Kate had not been invited to attend the wedding of William’s father, Prince Charles, to Camilla Parker Bowles earlier that year, so this could be seen as progress, not just in terms of the budding romance between the future Cambridges but also in terms of Kate’s style evolution. She’s elegantly dressed, albeit not nearly as put-together as she appears today.
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Kate steps out in Uggs
In April 2006, Kate does some last minute shopping before she and William head to Mustique for a holiday. She’s wearing a pair of soft and cozy Ugg boots, with her jeans tucked in, as was the fashion back then. Thirteen years later, she’s rarely, if ever, seen in such a seemingly unintentionally-casual look.
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“We were on a break”
It wasn’t the first time they’d split up (there’d been rumours of a brief split in late 2004), but Kate and William’s 2007 split was probably their most significant. Here, Kate’s seen partying in London in April 2007, shortly after the breakup made the news. By summertime, the two lovebirds had rekindled their romance.

They’re an “official” royal item
By 2008, the relationship between Prince William and Kate Middleton was stronger than ever, and on June 16, she attended the Order of the Garter service at Windsor Castle, which is her very first official appearance at a formal royal event.
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Prada plus platforms
At the Charity Polo Match at Cirencester, Britain on June 7, 2009, which Kate attended with Prince William, Kate wears a casual outfit accessorized with a Prada handbag, upping her casual fashion quotient significantly from previous years. That said, she’s wearing platform shoes, which Queen Elizabeth II reportedly discourages members of the royal family from wearing (remember, Kate’s not yet a member of the royal family in 2009).

A royal fiancé makes her debut
In October 2010, Prince William proposed marriage to Miss Catherine Middleton, and she accepted. On Dec. 18, the future royal spouse makes her debut as a royal fiancé at the Teenage Cancer Trust Christmas Spectacular and Reception in Norfolk, Britain. Reflecting her new status as a presumptive member of the royal family, she dresses the part in an elegant black and white dress by designer Alice Temperley and black velvet jacket, accessorized with what will become her signature handbag look (a small clutch), sheer black stockings, and dainty pumps.

Two more weddings
On Jan. 8, 2011, royal fiancé Kate Middleton attends the wedding of Harry Aubrey-Fletcher and Sara Louise Stourton at St. Andrew’s Church in Aldborough, Boroughbridge, Britain. She accessorizes her Libélula dress with a pillbox hat, as royals do, and she walks with her bodyguard, Karen Llewellyn. On April 29, 2011, she marries Prince William. Henceforth she is styled as Her Royal Highness, The Duchess of Cambridge, Countess of Strathearn, and Lady Carrickfergus.
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Pregnant with Prince George
In December 2012, it’s announced that Kate and Willliam are expecting their first child. Kate, pictured here looking about as run-down as we’ve ever seen her, is so ill with morning sickness that it’s speculated she’s having twins. Spoiler alert: she didn’t have twins. Prince George was born July 22, 2013.

Looking royally pregnant
Entering her third trimester with Prince George, the Duchess of Cambridge looks wonderfully elegant at the National Review of Queen’s Scouts at Windsor Castle, Berkshire, Britain on April 21, 2013. She’s wearing an intentionally-frayed mint green cotton tweed coat by Mulberry, a taupe beret by Whitely, and nude pumps by L.K. Bennett.
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Brightly attired for a tribal trip
On April 7, 2014, the Duke and Duchess of Cambridge visited Wellington, New Zealand and met with Maori tribesmen. Kate is wearing a bright-red, double-breasted Jenny Packham dress, accessorized with a matching pillbox hat and matching black clutch and pumps. “British designer Jenny Packham is known for her sophisticated, feminine styles, which makes her a perfect fit for the always-elegant Duchess of Cambridge,” Hello! Magazine explains in 2018.

Pretty in pink, pregnant with Princess Charlotte
In her third trimester of pregnancy with Princess Charlotte, Kate turns up at the Commonwealth Day Observance at Westminster Abbey, London, Britain on March 9, 2015, wearing a pale pink Alexander McQueen coat with pearl buttons, and we think she couldn’t look more elegantly feminine.

A more mature look is evolving
On a visit to India on April 11, 2016, Kate wears a perfectly tailored cream-coloured midi dress by Emilia Wickstead, whose clean, almost corporate look is becoming a favourite of the Duchess of Cambridge.

Kate gets suited up
Speaking of corporate, the Duchess of Cambridge truly looks as if she just as easily could be a Fortune 500 CEO in this Gucci textured tweed dress, which she’s wearing on a June 29, 2017, visit to the V&A Museum in London.

Pregnant and channeling Dr. Zhivago in Sweden
On a visit to Sweden on January 30, 2018, Kate, who is pregnant with Prince Louis, wears a gorgeous forest-green Catherine Walker coat with asymmetrical buttons and a furry collar, and she accessorizes it with a Dr. Zhivago-inspired fur hat (it’s not the first time she’s worn this wintry-but-warm look, one which her grandmother-in-law, the Queen also enjoys wearing) and Mulberry handbag and boots.
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