It was 1997. London was humid. Princess Diana stepped out of the Chelsea Harbour Club, and without even trying, she basically invented the "athleisure" trend that currently dominates every Instagram feed and TikTok "get ready with me" video. She wasn't wearing a gown or a tiara. Instead, she was sporting a pair of peach-colored biker shorts and a heavy, navy blue Princess Diana Northwestern sweatshirt.
That specific look—the oversized crewneck, the short leggings, the chunky white sneakers with tube socks—is etched into the collective memory of fashion history. But why Northwestern? Why would the Princess of Wales, a woman with the entire world's wardrobe at her fingertips, choose a midwestern American university logo for a workout in London?
Honestly, the answer is simpler than the conspiracy theories suggest. It wasn't a secret message about moving to Chicago or a political statement. It was a gift.
The Story Behind the Purple and White
Diana never actually set foot on the Northwestern University campus in Evanston, Illinois. She didn't have a secret degree, and she wasn't a closet Wildcats fan. The connection came through her friend, Jayne Fincher, a royal photographer, whose son was a student at the university. However, the more documented link is through her personal connection to the university's then-president.
In 1996, Diana visited Chicago for a massive fundraising event for cancer research. During that three-day whirlwind tour, she stayed at the Drake Hotel and charmed the entire city. She was gifted a massive haul of university swag, including that now-famous sweatshirt. Most royals would have tossed such a casual gift into the back of a closet or handed it off to staff. Not Diana. She wore it. Multiple times.
She wore it because it was practical. More importantly, she wore it as a shield.
By the mid-90s, the paparazzi frenzy surrounding Diana had reached a fever pitch. She was the most photographed woman in the world. Every gym visit was a battle. She famously realized that if she wore the same outfit to the gym every single day, the photos would have less value to the tabloids. They were "boring." Using a Princess Diana Northwestern sweatshirt as a repetitive uniform was a tactical move to devalue the invasive currency of her own image.
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It worked, kinda. The photographers still took the pictures, but because she looked the same in every shot, the "newness" vanished.
Why This Specific Sweatshirt Became an Icon
There’s something about the typography. The bold, arched "NORTHWESTERN" in white across a deep navy (or sometimes appearing dark purple depending on the film grain of the day) just hits different. It represents a specific era of 90s Americana that felt exotic in London but relatable in the States.
Fashion experts, like those at Vogue or the curators at the Victoria and Albert Museum, often point to this outfit as the moment the "Royal" brand shifted from untouchable deity to human being. It was the "People's Princess" in a physical garment.
The Fit Matters
You can’t just buy a modern, slim-fit hoodie and expect to look like Diana. Her sweatshirt was massive. It was a heavy-weight cotton blend, likely a Champion or Gear for Sports brand, which were the standard suppliers for college bookstores in the 90s. The sleeves were long enough to cover her hands. The waistband was thick.
If you're looking to replicate this today, you have to look for "vintage wash" or "reverse weave" styles. Modern fast-fashion replicas often get the weight wrong. They’re too thin. They don't have that structural "crunch" that a real 90s sweatshirt has.
The Color Palette
While Northwestern’s official color is purple, the sweatshirt Diana wore often appeared navy in the harsh flash of paparazzi bulbs. This ambiguity is part of the charm. It wasn't a bright, neon athletic piece; it was muted. It paired perfectly with those Virgin Atlantic sweatshirts she also rotated through, or the Harvard ones. But the Northwestern one remains the most searched for because it represents her most famous trip to the United States.
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The Cultural Longevity of the Look
Fast forward thirty years. We see Hailey Bieber recreating the exact paparazzi shots for Vogue Paris. We see Kendall Jenner and Bella Hadid rocking the oversized crewneck and biker shorts combo. It’s a silhouette that shouldn't work—it cuts the leg off at an awkward spot—but on Diana, it looked athletic and chic simultaneously.
There is a psychological element to why we still care about the Princess Diana Northwestern sweatshirt. It represents a woman reclaiming her narrative. In 1997, Diana was divorced. she was finding her own voice outside the "Firm." Choosing to wear an American university sweatshirt was a subtle nod to a life lived on her own terms, away from the stuffy protocols of Buckingham Palace.
It’s the ultimate "don't look at me, but look at me" outfit.
Spotting a Real Vintage Piece vs. a Modern Repro
If you’re hunting on Depop, eBay, or at a local vintage shop, you’re going to find a lot of fakes. Everyone wants a piece of this aesthetic.
- Check the Tags: Look for 90s-era tags like "Champion Eco," "Lee Sport," or "Tultex." If the tag looks brand new or is printed directly onto the fabric, it's a modern reproduction.
- The Print: The original was screen-printed with a slight puff to the ink. It should feel slightly raised. If it’s a flat sublimation print that feels like it’s part of the fabric, it’s a cheap modern knockoff.
- The Fabric Weight: Genuine 90s sweatshirts were heavy—usually 12oz or higher. They are surprisingly warm.
The original sweatshirt Diana actually wore? That's a different story. Many of her personal items were auctioned for charity or kept by her family. But the style belongs to the public now.
How to Style the Look Today Without Looking Like You're in a Costume
Look, wearing a Princess Diana Northwestern sweatshirt with biker shorts in the middle of a suburb can feel a bit like you're trying too hard to be a 1996 mood board. To make it work in 2026, you have to lean into the "high-low" mix.
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Try pairing the oversized sweatshirt with tailored trousers and a loafers. This elevates the look from "just left the gym" to "intentional street style." Alternatively, if you are going the biker short route, ditch the tube socks for high-quality ankle socks and a very modern, technical running shoe.
The goal isn't to cosplay as a late princess. The goal is to channel her "I have things to do and I don't care who's watching" energy.
The Lasting Legacy of the Northwestern Connection
Northwestern University itself has a complicated but proud relationship with this moment. They aren't exactly running "As Seen on Diana" ads in the student bookstore, but they are fully aware of the sweatshirt's legendary status. Every few years, when a new season of The Crown drops or a fashion house references the 90s, the school sees a spike in interest for that specific navy-and-white design.
It is rare for a piece of clothing to bridge the gap between British royalty and American collegiate life so seamlessly. It reminds us that style isn't about the price tag—it's about the context.
Diana took a $40 piece of campus merch and turned it into a symbol of independence. She took a gift from a trip to Chicago and used it to hide from the world, and in doing so, she became more visible than ever.
Actionable Steps for the Aspiring Stylist
- Audit Your Fit: If you want the Diana silhouette, buy two sizes up. The "oversized" look only works if the shoulder seams actually drop down the arm.
- Source Quality: Search for "Vintage Northwestern Crewneck" specifically on sites like Grailed or Etsy. Look for "Made in USA" labels for the most authentic 90s feel.
- Focus on the Shorts: If you're doing the biker short look, ensure the hem hits mid-thigh. Too short, and you lose the "athletic" vibe; too long, and it looks like 80s aerobics gear.
- The Shoe Factor: Stick to clean, white, chunky silhouettes. Think Reebok Club C 85s or New Balance 990s. These ground the outfit in a way that modern knit sneakers simply can't.
- Invest in a Heavyweight Blend: Avoid 100% polyester. You want a 80/20 cotton-poly blend to get that specific drape that characterizes the Princess Diana Northwestern sweatshirt era.