This time last summer, most of us were glued to the TV watching documentaries and news specials on the 20th anniversary of Princess Diana’s death. She was a rule-breaker, a trailblazing philanthropist, and, without a doubt, a fashion icon—in fact, her style evolution functions as a visual timeline of her growing confidence and achievements as a royal and mother. In Diana’s early days as a new princess, when she was affectionately known as “Shy Di,” she often wore awkward, matronly tweed jackets in an effort to look more grown-up. But as she actually grew up and into the outspoken, undaunted woman we all remember, she dressed the part and then some. Facing hundreds of cameras on a daily basis, she looked unfazed in her strong-shouldered dresses and crisp suits. Her bold late-’80s style became so synonymous with Diana that, to this day, fashion types can describe a piece as being “a little Princess Diana” and you immediately know what they mean. (Virgil Abloh even designed an entire Off-White collection in her image.)
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But even when Diana wasn’t meeting with ambassadors or hitting the red carpet, she had a singular look. Some of our favorite photos capture the “Queen of Hearts” at her most casual, whether she was playing with her sons in a belted jumpsuit or vacationing in a printed day dress. (Admittedly, these were likely moments when she most didn’t want to be photographed, but as we know, the paparazzi were ruthless.) Even when she was just wearing jeans and a sweater, she always looked elegant; compared with the sloppy hoodies and sweatpants of today, it’s a different form of casual that feels particularly fresh. Here, on what would have been her 57th birthday, we’re revisiting some of our favorite summer looks, plus how to get them now. New York is expected to reach nearly 100 degrees Fahrenheit today, so that leopard slip looks especially tempting.