10 Times Princess Diana Dared To Wear Menswear

Although the idea of bending gender norms in fashion may seem new and modern to some, a quick look into Princess Diana‘s best fashion looks proves that might not be the case. In fact, the late Princess of Wales was no stranger to pushing the boundaries of fashion, from what was considered “in style” to what was considered feminine.

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In a few moments in her years as royal, Diana dared to wear menswear and looked absolutely gorgeous while at it. In 1988, for example, Diana wore one of her more “masculine” looks as she attended a charity greyhound racing event at Wembley Stadium. At the event, the royal looked radiant as she paired a green Hackett waistcoat, a Catherine Walker suit and a matching black bow tie.

And although the look is cool and chic for a person of any gender to wear today, we can’t help but think of the boundaries she broke when she decided to put that on that day. Instead of the traditional dress or skirt, she welcomed a suit instead. Given the time, we’d say it was quite groundbreaking!

So, in honor of her trailblazing menswear looks over the years, we compiled them all below!

  • White Tux

    Image Credit: Jayne Fincher/Princess Diana Archive/Getty Images

    In this Feb 1984 picture of Diana, she can be seen smiling from ear to ear as she wears a gorgeous Margaret Howell white tuxedo at an event. So crisp and chic!

  • The Green Number

    Image Credit: Princess Diana Archive/Getty Images

    In 1988, Diana undoubtedly turned heads in this three-piece suit with an emerald green Hackett waistcoat while attending a greyhound racing event in 1988. 

  • Suiting Up

    Image Credit: Tim Graham Photo Library/Getty Images

    In another one of her suit moments, Diana blended masculinity with femininity in this white suit, white skirt and black bow tie by Jasper Conran while visiting Florence, Italy, in April 1985.

  • Keeping It Casual

    Image Credit: Julian Parker/UK Press via Getty Images

    While visiting her brother Charles Spencer’s new baby at St Mary’s Hospital in 1994, Diana gave her spin on menswear yet again in this navy suit, white button-down and navy-patterned tie. We’re loving the sweet gold elephant motif here!

  • An Eagles Fan

    Image Credit: Jayne Fincher/Princess Diana Archive/Getty Images

    During a visit to Prince Harry’s school in 1991, Diana sported this menswear jacket from the Philadelphia Eagles. Who knew the Princess was into football? 

  • Cool for School

    Image Credit: Jayne Fincher/Princess Diana Archive/Getty Images

    Diana opted for another letterman jacket while dropping off Harry a year later in 1992. 

  • Cozy in Brown

    Image Credit: Tim Graham Photo Library via Getty Images

    In 1990, Diana wore another similar relaxed menswear jacket while doing another school drop-off.

  • Polo Ready

    Image Credit: Tim Graham Photo Library via Getty Images

    In addition to wearing a boyfriend-style pair of jeans, Diana was also embraced some masculine fashion items in the oversized black blazer and baseball cap.

  • All in the Blazer

    Image Credit: Daily Mirror/Mirrorpix/Getty Images

    Back in 1989, Diana made headlines when she paired these brown boots and white shirt and pants with this mens-style blazer and baseball cap. If you ask us, we totally love it!

  • Statement Blazer

    Image Credit: Tom Wargacki/WireImage

    In this 1994 look, Diana wore another long blazer that totally stole the show from the otherwise white and brown look.

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