How Princess Diana Made Ugly ‘90s Trends Look Chic (You Can Too)

Princess Diana was called “the people’s princess” because she had a way of connecting with the public that just hadn’t been seen in the royal family before. She cared about people, would go out there and “love people and show it.” But despite her reputation as the “people’s princess” and the idea some people, especially Americans, have that she was a commoner, she was actually born into British nobility. And she grew up not too far away from the palace in Sandringham, England.

She remains known for the normalcy she tried to give Prince William and Prince Harry as children. Diana made the choice to be more present in their lives than previous generations were very early on. It’s been reported that Queen Elizabeth II, who also said she wanted her children to be raised as normally as possible, generally only saw her children twice a day at family “meetings.” 

When Diana brought her children with her on her travels, it was at first met with criticism. Change often is. But it very quickly grew on people because it’s only natural for a mother to want to be with her children. That made Diana relatable. So public school and regular trips to McDonald’s were all part of the royal program. 

Princess Diana also became the queen of people’s hearts for her sense of style. She became a fashion icon whose sense of style was copied all over the world, not only while she was alive, but is still emulated today. It wasn’t overly fussy or even trying to set trends, it was just her. And so seemingly without trying to, Diana wore many of the “ugly” ‘90s clothing trends in an effortless way that somehow managed to be chic. Let’s get into just how she did it. 

Bike Shorts

Perhaps the most re-popularized (at least recently) “ugly” ‘90s trend that Princess Diana proudly wore is bike shorts. If you associate these with being just something for people super into biking, or with the Kardashians who brought the shorts back into style, you’re missing out on the ultra-chic way Lady Di wore bike shorts.

Princess Diana’s exercise and loungewear style is so ingrained in the fashion sphere that model Hailey Baldwin Bieber styles them like Di. To wear bike shorts the Princess Diana way you’ll want an oversized college crewneck, rectangular small ‘90s style sunglasses, dad sneakers, and chunky white gym socks. So skip the heels you’ll sometimes see Kim K pair with bike shorts in favor of a royal-inspired ensemble. 

Sweater Vest

You heard me, the sweater vest is back. And it doesn’t have to stay as a private school uniform exclusive item either. Princess Diana made these an easy outfit basic by pairing them with a collared shirt. And for Lady Di-level style, consider coordinating the color of the vest and button-down like she did. 

Mom Jeans

The word around TikTok is that Gen Z has given up skinny jeans in favor of the looser styles popular in the ‘90s. (Here are some cute ways to wear them.) Princess Diana is, as always, on top of this “ugly” ‘90s trend. Her secret is to keep it simple. A basic shirt and jacket make the difference between these jeans being part of a ‘90s outfit versus the crop tops today’s teens might wear instead. Stick to the former for chic Diana-inspired style. 

Ugly Sweater

You know that trend you thought was going to stay at Christmas parties? Yeah, the so-called tacky sweater look was Diana-approved. And why not? Bold, chunky sweaters are a lot of fun. 

The ensemble was such an iconic look of Diana’s that Harry Styles actually recreated it. (Although we’re certain Diana won this who-wore-it-better battle).

Overalls

You saw them on Rachel and Monica in the ever-relevant ‘90s fashion of Friends, but Princess Diana made them work for her life as a royal too. Her preppy poplin adds a touch that makes the outfit uniquely Diana. So find yourself a floral blouse and a pair of overalls that subtly coordinates. That’s overalls done right. 

Cardigan

If you wouldn’t dream of putting an oversized cardigan over a gorgeous dress, this glowing photo of Princess Diana is just about the only thing that has any chance of making you reconsider. The key is a high-quality knit where the material and construction look gorgeous and won’t take away from your dress.

Bomber Jackets

You may have been happy to see the bulky bomber jackets of the ‘80s and ‘90s go. But this ‘90s trend was a favorite of Diana, and a casual style staple she wore when she was focused on her boys and not on royal duties. So for an outfit perfect for the average gal, don’t neglect to try a bomber jacket. 

Dad Shoes

Chunky sneakers are cool, but you have to wear them the right way. The classic Lady Di look is of course some good old-fashioned bike shorts and a sweatshirt. But really you could make these work with many of the casual pieces Diana loved like bomber jackets and sweater vests. Who said these were “dad shoes” anyway?

Closing Thoughts

Her glow, personality, and sense of style all combined to make Princess Diana an unparalleled fashion icon. She effortlessly made the “ugly” fashion trends of the ‘90s work. So whether you go out and buy an item to try an old ‘90s trend or you dig through the depths of your closet to decades past, Princess Diana wore ‘90s outfits worth recreating. 

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