Princess Diana’s '90s-inspired sweater styles that are making a comeback this winter

As sweater season is fast approaching, who better to take inspiration from than our beloved fashion icon, Princess Diana? From skirted suits to mom-fit jeans, her sweater game with every ensemble looked chic, sophisticated, and unique. Leaving the 90s in awe with her over-the-top futuristic fashion sense, little did we know that this 90s trend is making a sharp comeback this fall, where people are going all gaga over oversized collar-style sweatshirts and more. Princess Diana was known to find the sublime in the tacky, turning gaudy into something chic and elegant. An inspiration for us all, let’s see five of her 90s-inspired sweater styles that are perfect for this fall.

Diana was never into British sports, but her husband, King Charles, enjoyed the sport of polo more than anything. By wearing a statement high round neckline oversized navy blue sweater featuring a polo print, it was her way of silently supporting him. She was once seen wearing this statement piece paired with a white straight-flared dress with a ruffled high neckline, which acted as the collar of the sweater, giving a 90s vision. Thanks to the trending horse girl aesthetic in 2025, you can find such pieces with classic options from the racks of Ralph Lauren.
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While dropping Prince Harry off at his first day of school in 1989, she was seen wearing a bright red oversized sweater, but it came with iconic family heirlooms. The sweatshirt had statement pearl embellishments, which created a flower-like design and looked absolutely ravishing. Some may find this gaudy, but not in 2025 anymore, as many brands like Farfetch and others have released similar-looking sweatshirts with statement embellishments, perfect for your nights out.
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While doing a school run for her kids in 1989, Princess Diana was spotted in a navy blue and white striped buttoned cardigan, which still remains a trend to this day. This cardigan is available at Jenni Kayne and captures the exact oversized look that Princess Diana had. She teamed it with a full-length flared white skirt, exuding a perfect contemporary winter look. Striped print cardigans are making a huge comeback this year, so make sure to have a versatile pick in your wardrobe.
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Princess Diana was often spotted in oversized sweaters, which came in vibrant colours and statement prints. She was once seen in a round-neckline sweatshirt drenched in red drama, which had the infamous ‘black sheep’ with white sheep printed all over the bodice. This crewneck spoke volumes about her perceived place in the royal family, and honestly, it was very adorable. You can get the same print and colour at Rowing Blazers this winter.
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This sweater screams ‘I want to dress up, but I like to party’ and can be worn with any and everything in your wardrobe this year. Diana opted for a white V-neckline print sweater and teamed it with her all-white flared pleated skirt. These white sweaters with a navy blue or black outline on the V-neckline exude an old-money charm, which has made people go gaga over the look. So, if you’re one of them, then this is your cue to purchase one this year.
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