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British princesses dress differently than you and I, and not just, to paraphrase Hemingway, because they have more money. They, in fact, dress very differently than their fellow celebrities who have much more money. Most celebrities, especially female ones, dress to hold the public’s attention. There are a lot of ways to do that. You can wear a dress held together with safety pins like Elizabeth Hurley, or $18 million Oscar outfits like Cate Blanchett, or opera gloves and pearls and nothing else like Kim Kardashian.
Royals can’t do any of that. They have to dress not in a way that merits attention, but rather their countrymen’s approval—or, at least, doesn't merit their countrymen's disapproval. Because that’s kind of the whole point of being in the English monarchy, if we are to believe Queen Elizabeth II who, at 21, explained her role like this: "It is simple. I declare before you all that my whole life, whether it be long or short, shall be devoted to your service."
Since monarchs are always supposed to be pleasing their subjects, they can’t wear opera gloves and nothing else, even if they wanted to. They have to dress how you would if you were meeting your significant other’s parents or going to an office party. They are role models for dressing for situations where you will be judged.
They must adhere to what society deems acceptable, and for much of history, what society wanted was women whose clothing played up either the fact that they were virgins or eternally devoted to one man.
Queen Elizabeth the First wore tons of pearls because they represented chastity. She also wore her coronation ring on her left ring finger because, according to Allison Weir in The Life Of Elizabeth I, it symbolically wedded her to her people. Queen Victoria wore black mourning attire for decades after the death of her husband Albert. In both of their lifetimes, a woman showing her sexuality would be shamed, and Elizabeth and Victoria found interesting means to avoid that.
The first female royal who managed to adopt an openly sexy style was Princess Diana. When she and Prince Charles married in 1981, Diana was supposed to be as much a virgin bride as any other royal, and for a long time she dressed to reflect that. When you think of early Diana, you think of pearl necklaces (they still symbolize chastity!) and schoolgirlish Peter Pan collars.
For years she avoided dressing at all provocatively; when Christina Stambolian designed a dress for her in 1991, she refused to wear it because it was too sexy. However, she did wear it three years later in 1994, on the same day Charles admitted to an affair with Camilla Parker Bowles. It became known as the "revenge dress" and people loved it.
Kerry Taylor, who auctioned off many of Diana’s clothes in 2013 said, "Her influence meant that royals didn’t have to be dowdy. You didn’t have to wear pastel colors, a massive handbag, and hat. You could love fashion and look good." That view was very much in keeping with the times. Sex and the City would debut a mere four years after.
But there are other British royals for whom being deliberately unstylish was just as important. In the 1930s, Wallis Simpson—Prince Edward’s divorcee mistress for whom he abdicated the throne, claiming he could not fulfill his duties as king without the support of the woman he loved—was probably the most well-dressed woman in the world. She swanned around in Schiaparelli evening gowns with prints personally designed by Salvador Dali. It was bananas how good she looked. Just spend a minute Googling her outfits, they’re pretty much all great.
But, cool fact, she and Edward were also horrible people. In spite of what Madonna’s W.E. movie tries to tell you, they were almost certainly Nazi sympathizers. Wallis supposedly had an affair with von Ribbentrop. She and her husband would have traded away England for a well-made martini. Winston Churchill once said that a statue of Wallis should be erected in every town in England because she saved the country from Edward.
After Edward stepped down, George VI became king and his wife Elizabeth became queen. She very pointedly dressed in what would be considered '40s normcore. She was deliberately dowdy. People who loved Wallis Simpson criticized her for this endlessly, but no one, then or today, would be able to compete with Wallis on the style front.
By dressing in fairly shapeless dresses and frumpy hats, she reminded the people that the monarchy wasn’t really about looking great, it was about service to the people. Plus, when she went to visit citizens who had been bombed in the Blitz, it would have been incredibly insensitive to show up in a Schiaparelli evening gown. That’s not to say she dressed poorly—her clothes could be described as generally serviceable and appropriate—but no one would describe her as fashion-forward. This actually made her more likeable.
This is also a legacy that extended onward to her daughter Queen Elizabeth II, who dresses not all that differently from her mother, though she’s added some brighter, peppier colors, like the bright pink she wore after the birth of baby Charlotte was announced.
Kate Middleton seems like she’s managed to land somewhere in between dressing in the practical manner of the Queen and Queen Mother and Diana’s bombshell style. It appears to be working out pretty well, too; as of 2013, confidence in the British monarchy was at an all-time high.
And her daughter? Princess Charlotte was last seen wearing an admirable white cap and white blanket, which no one can disapprove of just yet.