Celebrity Style

The Princess Diana Way To Master 'Ugly' '90s Trends

From sweater vest to chunky sneakers.

From cardigans to chunky sneakers, here are the top “ugly” ‘90s trends that Princess Diana mastered ...
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Though Princess Diana’s evening gowns, revenge dresses, and jewelry items are among the most iconic looks of all time, it was her off-duty looks that had her mastering some of the trickiest and most controversial of ‘90s fashion trends. But, as she did with everything else, she not only made her way through the head-turning looks of the decade, but also made them look covetable — even today. And Princess Diana’s ‘90s outfits are full of inspo for your wardrobes now.

When it came to her personal style, Princess Diana hit it out of the park each and every time. And that goes for both the classic floral dresses as well as the “uglier” trends of the decade like bike shorts, chunky sneakers, and cardigan sweaters. They are trends that were not only quickly part of the lexicon in the ‘90s, but are now experiencing quite the resurgence — with everyone from Hailey Bieber to Lizzo embracing these styles today.

Ahead, find the top “ugly” ‘90s trends that Princess Diana mastered that are still inspiring today.

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Though denim might not be the first trend that comes to mind when you think about royals, it’s one of the most-loved off-duty looks from Diana. She took it to the next level, mastering one of the trickiest ‘90s trends, layering denim on denim for a Canadian tuxedo look on the regular.


Bike Shorts

Bike shorts are the athletic trend that divides us all, with lovers and haters standing in stark contrast to one another. Princess Diana was known to layer on an oversized sweatshirt, tube socks, and head out for a workout class or quick errand, even while still an official working Royal.


Chunky Sneakers

Though minimalism prevailed in decades that came after, the ‘90s was all about the chunky “dad” sneaker. It was one, whether with bike shorts or jeans, that Diana always wore like a pro.



Cardigans worn as an over layer, an under layer, or simply buttoned up as a top, were popularized in the ‘90s with the emergence of grunge. Be it Audrey Hepburn-style layering over a dress, or a more oversized throw-on-and-go, Princess Diana was known to wear cardigans regularly.


Sweater Vests

Another ‘90s “dad” trend that Princess Diana stepped out in on a regular basis was the sweater vest. She would often layer them over a button-down shirt, sleeves rolled to her elbow, paired with either jeans, cropped pants, or a midi skirt alike.