Seven Iconic Princess Diana Outfits That Didn’t Make It Into The Crown
Hint: They’re even better than the “revenge dress.”
Just over three weeks ago, I plopped down on my couch and devoured the first two episodes of The Crown’s sixth season. One evening later, and I’d finished all four. At that point, there was nothing left to do but wait for Part 2 to come out—and scroll through images of Princess Diana’s iconic outfits.
The sweater with the black sheep. The puff-sleeved wedding gown. The “Fly Atlantic” sweatshirt. The black “revenge dress.” These are the specific images we remember and recirculate time and time again, but there’s so much more to Diana’s fashion. In fact, I’d go out on a limb to say that, collectively, her less obsessed-over looks better embody why her style remains universally appealing to this day.
Just like all of us, Princess Diana contained multitudes—and so did her clothing. Oftentimes, she relied on timeless tailoring, but she also wasn’t afraid to experiment with trends. She’d don a ladylike suit one day and pull off laidback athleisure the next. She was sophisticated. She was sexy. She was formal. She was fun.
In an effort to embrace every aspect of our identities, I think we can all take notes from Diana’s widely varied wardrobe: Below, a snapshot of Princess Diana’s diverse sense of style—featuring seven of her most underrated outfits.
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7 Princess Diana Outfits
1. The Formal Suit
While most of us aren’t attending royal engagements or carrying around Dior bags, we can still enjoy luxuries like gorgeously tailored suiting. For your own version of this demure, all-black ensemble, layer the wool-twill Yiyan blazer over the square-neck Cynthia dress—a style that evokes ‘90s minimalism. The built-in belt, plus your glamorous pavé hoops, kitten-heel pumps, and black tights, complete this streamlined, sophisticated look.
2. The Button-Down and Blue Jeans
Diana’s off-royal-duty style was the very epitome of Power Casual—equal parts polished and practical. To recreate this particular combination—which is peak timelessly chic—pair a crisp white button-down with light-wash blue jeans, and add neutral accessories like the now-on-sale D-ring belt, the cognac Grace loafers, and the crescent-shaped Karis earrings.
3. The Bright Evening Gown
Diana’s red carpet looks were sleek, colorful, and confident—an aesthetic you can easily translate into everyday life with a few tweaks. If you’re heading to a holiday work party, swap the gown for a knee-length style like the Jillian dress, which features a slightly relaxed bodice and an artfully gathered waist. Silver sandals and dangly earrings finish off your festive look better than the Crown Jewels ever could.
4. The Trench Dress
Diana was definitely clever enough to repurpose her trench dresses as jackets, but hers certainly weren’t made from OrigamiTech. Wrinkle-resistant, lightweight, and machine-washable, our signature OrigamiTech fabric was designed with travel in mind but works for a wide range of settings—as if the Gwynne trench dress wasn’t insanely versatile already. Round out this minimalist look with classic accessories like black pumps and vintage-inspired earrings.
5. The Red Sweater
You, too, can turn heads wherever you go—especially if you wear an eye-catching sweater like the Kiki. In addition to its juicy strawberry hue, it features a unique knitting pattern you won’t find anywhere else and acts as the perfect accessory when draped over a white button-down like the Lagarde shirt. To emulate Diana’s look, slip on the olive Colby pants and a pair of pointed-toe flats.
6. The Houndstooth Set
Houndstooth is one of those patterns that never falls out of favor. Case in point: Our Yiyan blazer and Maisie dress look a lot like this outfit—just a little less ‘80s. Made from our stretch houndstooth, each piece has a classic aesthetic and innovative flexibility. To let your suiting set steal the show, pair it with coordinating accessories like black pumps, sheer tights, and pearl earrings.
7. The Cigarette Pant
Whether you’re leaving a posh tennis club or running to the grocery store, trading your weekend sweats for slightly elevated essentials will help you feel a lot more put-together. A relaxed sweater plus a skinny pant will form a fantastic off-duty uniform; try the fine-alpaca Cathy sweater and the legging-like Curie pants, which come in two inseam lengths. If you want to go full winter-chic, add the metallic Grace loafers, a pair of gold hoops, and a roomy, Chablis-colored bag.