Kate Middleton’s Classic Style: How to Dress Like a Princess

As Prince William's lady has transformed from "Waity Katie" to the future Princess Catherine Elizabeth, her look has evolved too: Out are the flashes of midriff, in are simple makeup and understated British designers. Rebecca Dana on Britain's stolid new fashion icon. Plus, see pictures of how Kate's style stacks up against Princess Diana's.

Kate Middleton may be a commoner, but her style resembles Princess Diana's, at times astonishingly so. (Getty Images)

"Kate’s hot."

This was Prince William’s first recorded thought about his future princess, and its substance has never been in dispute. What has evolved over their eight-year courtship, as Waity Katie patiently won her mate, is not the degree of Middleton’s hotness but its status-securing corollary: taste. Now, as she stands on the doorstep of the House of Windsor, Catherine Elizabeth can reasonably be called “fashionable,” but it wasn’t always so.

Gallery: Kate Middleton & Princess Diana’s Fashion

Sparks first flew between Will and Kate at a fashion show, at St. Andrews, in 2002. She was on the catwalk, wearing a teeny weeny black bandeau bikini with some scaly gold netting overtop, looking like she just traipsed out of the Blue Lagoon. Straw was woven into her hair. Wills paid £200 ($318) for a front-row seat, and when the flight attendant’s daughter stalked by in her skivvies, the prince leaned over to his pal Fergus and announced the first stirrings of his royal heart.

Years later, once she began to fill out the role of “princess-in-waiting,” an archetype she essentially created, Kate swanned around in backless gowns from British designer Daniella Helayel’s Issa brand and hunted pheasants in hearty tweeds. “Classic and cool” is how people describe her style, and also “less is more.” Her wardrobe is primarily understated, her hair worn plain in shiny brown waves, her one indulgence the occasional whimsical hat. To announce her engagement, she wore a navy blue Issa dress and Princess Diana’s engagement ring, a dime-size sapphire surrounded by diamonds. Her fingernails were neatly trimmed but unpolished.

“Kate Middleton has a wonderful youthfulness about how she wears clothes and seems to equally enjoy putting on her jeans for an evening out with her friends in London as much as she does a whimsical feathered hat for a wedding or a colorful long satin evening dress for a black-tie party,” says Vogue style director Alexandra Kotur. She suggests Middleton look to the first lady for tips on high-profile dressing and hopes she’ll incorporate younger, less expected designers like CFDA finalist and fellow Brit Gregory Parkinson or London’s Meadham Kirchhoff into her royal wardrobe.

In the early days, it was occasionally rough going for the bouncy college girl. Compared to Diana’s urbane glamour, Kate was woodsy, youthful, and unpolished. She wore a lot of jeans. Slim-hipped and washboard-abbed, she showed a fair amount of midriff. She once went rollerblading in bright green sequined hotpants, which caused predictable uproar in the British press. This was a period Marie Claire U.K. referred to as the “frumpy and unsure” years.

In 2007, the couple took a short break from the relationship, which Kate didn’t want but during which she was able to “grow.” She returned to William looking eerily like his mother. Gone were any girlish slip-ups, gone were sequins and glitter eye shadow. In their place, she wore simple makeup and dresses that were fashionable but not overly so. She will never make the mistake of a Comme des Garçons sweater.

“In many ways, the key shift in her style happened a few years ago at the 2007 Cheltenham Gold Cup,” says Ella Kay, author of The Daily Kate, a blog about the future queen. “She showed up at the races wearing a stylish brown beret and a tailored blue jacket paired with a pashmina, and the British fashion press went crazy over it.” She’s favored flowy dresses and tailored jackets ever since. “Probably the thing she’s been criticized most for have been some of the costume outfits she’s worn to charity events, including a crazy roller disco fundraiser a few years ago, and, oddly enough, for her consistency—she tends to favor traditional, classic pieces and wears them again and again, which some people find boring.”

Middleton since has become something of a fashion icon in Britain, but a dull one, the opposite of British fashion fiends like Isabella Blow or Daphne Guinness. She is stolid and reliable, sartorially and in seemingly every other way, and that forms the essence of her appeal. If her manner of dress is any indication, this may be the first royal marriage not to dissolve into tabloid farce in generations.

Rebecca Dana is a senior correspondent for The Daily Beast. A former editor and reporter for The Wall Street Journal, she has also written for The New York Times, The New York Observer, Rolling Stone and Slate, among other publications.