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Don't miss out on "bike shorts and sweatshirts" fall.
As temperates finally dip across the country, this weekend marked the official beginning of fashion’s favorite time of the year: fall. That’s right, it’s finally time to whip out those cardigans, try out a trendy blanket scarf, dust off your favorite barn jacket, and layer it on thick with the autumnal accessories in shades of burgundy and chocolate brown.
There’s a virtual treasure trove of fall fashion inspiration just waiting to be upcycled in the celebrity archives. Take your cues from Lenny Kravitz and make a scarf statement with an outrageously oversized accessory. Or dip into the Olsen twin files with a black-on-black moment paired with a beat-up It Bag and retro sunglasses. When in doubt, though, there’s no better transitional fashion icon than Princess Diana.
The People's Princess was a master at dressing for the weather, thanks to her knack for combining wardrobe staples in quirky, unexpected ways. Diana's outfits never disappointed, but her unique blend of prep and high fashion truly shone during the fall. In fact, you probably already have many of her favorites hanging in your closet. Tuck a pair of comfy sweats into a pair of cowboy boots (a stellar combo also seen in Prada's latest runway show) à la Diana for an off-duty princess moment, or go for the classic bike shorts and sweatshirt pairing for the ultimate cool-girl weekend look.
You really can't go wrong with a Princess Di-approved fall outfit formula come fall, So, this is your friendly reminder, fashion girls: It's Princess Diana Season. Read on for some fresh inspiration and a look back at the royal's best sartorial moments—for Pumpkin Spice Latte weather and beyond.
Finally, It's Bike Shorts and Sweatshirt Weather
This is perhaps Princess Diana's most iconic fall look. Wearing bike shorts with sneakers and a big, comfy sweatshirt is the dream outfit for any fall weekend while the weather allows. It's effortless, cool, and, most of all, sports an artfully calibrated silhouette that balances proportion and charm like no other.
A Regal Take On Sweatpants
Once again, this look proves no one understood proportion like Lady Diana Spencer. It's all perfect: Her elegantly tucked linen pants billow just the right amount. Her tailored blazer adds a touch of structure. And her accessories—a baseball cap and cowboy boots—are right out of 2024's TikTok fashion playbook. Princess Diana walked so Gen Z could run.
Why Not Try a Quirky Knit?
As a Brit, Princess Diana was born to bundle up in a wool sweater every fall. But it’s her singular taste and renegade style that makes her knitwear collection one for the history books. This “black sheep” number is just one of many delightfully strange designs (with plenty of personality to spare) that the late royal kept in her rotation.
Weird Prep Never Goes Out of Style
The key to many a Princess Diana look is a high-low mix that makes an outfit so much more than the sum of its parts—and this is no exception. There's a practical genius to throwing an old varsity jacket over a silk skirt and tights, and the royal's gold hoops put a chic twist on an unconventional outerwear choice.
The Ultimate Princess Diana Fall Fashion Formula
While it might be a tried-and-true combination today, Princess Diana made the blazer-and-jeans pairing a modern classic. This outfit formula will never, ever go out of style—it looks just as good today as it did more than 30 years ago—and it's part of her enduring fashion legacy. Name a more iconic duo, I'll wait.
