Let’s Take a Minute to Dissect Diana’s Off-Duty Style

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princess diana bike shorts sloane ranger style
Photo: Courtesy of Getty Images

Boxy blazers, cowboy boots, bike shorts – did Princess Diana have a crystal ball into the future of fashion?

The 90s are back and, considering that she was style icon of the 1990s, it only makes sense that Diana’s preferences have become current again – so current in fact that every off-duty look we found of hers resonated with today’s trends in a major way. The best part? They’re completely unfussy, easy to cop, and surprisingly affordable. Here, we’ve broken three down with accompanying shoppables in honor of what would’ve been her 58th birthday.

On the Go

Even though it was a controversial choice at the time, Princess Diana practically lived in her cowboy boots. She wore them to polo matches, while running errands, and even on official state business. What’s more is that she often paired them with denim – another royal no-no. Take a moment to appreciate her sartorial defiance, then discover where you can create your own version of her iconic outfit.

1989 princess diana style
Photo: Courtesy of Getty Images

Short and Chic

You will not believe just how many photos there are of Princess Diana wearing bike shorts. She loved to be comfortable when she was working out, which is why she frequently favored one outfit formula: a chunky sweatshirt with bike shorts and chunky sneakers. Oh, and if that sounds familiar, it’s because it happens to be completely of-the-moment when it comes to fashion trends.

1995 princess diana style

Business As Usual

When it came time to make a good impression, Lady Diana reached for the unexpected. Instead of a fancy ballgown, she was happy in comfortable, no-nonsense suits. Given this year’s flood of oversized suits, you have plenty of icon-worthy options to choose from.

1997 princess diana style
Photo: Courtesy of Getty Images
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