Almost 30 years have passed since the death of Diana, Princess of Wales, but her way of dressing remains surprisingly current. Just by revisiting some of her most spontaneous photographs, you can discover outfits that could perfectly belong in the wardrobe of any woman this autumn. High-waisted jeans, knit sweaters, sporty-inspired jackets, and cowboy boots are some of the garments the princess wore decades ago and that still work today.
Although her gala dresses and her most elegant looks have gone down in history, it is probably her way of dressing off the official engagements that has best withstood the test of time. Diana had a special knack for combining classic pieces with other more casual items, mixing different styles and making outfits that seemed simple carry a lot of personality.
It is precisely that facet that proves interesting again in Fall 2026. In a season in which we are bringing back suede jackets, bomber jackets, cardigans and the western-inspired footwear, her wardrobe offers numerous ideas that we can adapt without having to copy every detail. These five style formulas show that some of the best autumn combinations were already worn by Diana, Princess of Wales, more than three decades ago.
1. Cardigan, White Skirt, and Two-Tone Shoes
One of the most elegant combinations we find in Diana’s wardrobe is also one of the simplest. On this occasion, the princess chose a white skirt that she paired with a thick-knit cardigan. She completed the look with a black bag, sunglasses, and black-toed shoes that contrasted with the rest of the design.
Diana, Princess of Wales, with a knit cardigan, skirt and two-tone flats.
The interesting thing about this ensemble is the mix of garments we typically associate with different seasons. The skirt, light and flowing, takes on an autumnal feel when paired with a dark cardigan, while the two-tone shoes provide a particularly sophisticated touch.
To recapture this formula in 2026 we can opt for a white midi skirt or a simple-cut dress and pair it with a black cardigan with jewel buttons. A pair of low-heeled pumps or two-tone flats complete a look that works both for the office and for a special meal.
2. Bomber Jacket, Jeans, and Cowboy Boots
Long before university-inspired jackets became headlines again, Diana was already incorporating them into her more informal looks. One of her most recognizable combinations features a red and black bomber with leather-like sleeves, high-waisted blue jeans, and brown cowboy-inspired boots.
The result has a very 90s aesthetic, but precisely for that reason it remains easy to move into the present. The bomber adds volume on top, while the straight-cut jeans balance the proportions and the boots add a relaxed touch.
Diana, Princess of Wales, with cowboy boots and a bomber jacket.
This autumn we can recreate it with a university-inspired bomber, classic blue jeans, and brown leather boots. It isn’t necessary to reproduce the exact colors of the original look: a burgundy jacket, bottle-green, or navy blue can work just as well. The secret lies in pairing a sporty piece with others that have a more classic character.
3. Knit Sweater, Light-Wash Jeans, and Tall Boots
If there is one formula that proves we don’t need overly special pieces to dress well in autumn, it is the combination of a knit sweater, jeans, and tall boots. Diana used this pairing on numerous occasions, opting for comfortable pieces that managed to convey a relaxed image without looking careless.
In one of her most memorable photographs she appears with a light-blue turtleneck sweater with floral details, light-wash jeans, and brown knee-high boots. The blend of soft colors with the leather of the boots achieves an especially interesting balance.
Diana, Princess of Wales, with light-blue jeans, cowboy boots and chunky knit sweater.
One of the keys lies in the silhouette. The sweater has some volume, but sits slightly fitted at the waist, while the jeans keep a simple line. The boots, on the other hand, add personality to the outfit and make it look more polished.
4. Burgundy Puffer, Green Sweater, and Black Trousers
Diana also knew how to make practical garments interesting. In another of her everyday style photographs she appears wearing a short burgundy puffer, a green sweater, dark trousers, and brown cowboy boots.
Diana, Princess of Wales, with a burgundy puffer.
Although it is an outfit designed for comfort, it has several details that make it a good reference for autumn and winter. The first is the combination of burgundy with green, two colors that work especially well together and allow escaping from the usual all-black outfits.
5. Brown Suede Jacket and Printed Midi Dress
The last formula demonstrates another of Diana’s great talents: pairing romantic pieces with other more casual-inspired ones. In this photograph she appears with a multicolored printed midi dress and a belt that cinches the waist, accompanied by a brown suede-looking jacket and light-colored low-heeled shoes.
The combination is especially interesting due to the contrast between the different textures. The dress has movement and a striking print, while the jacket provides a more relaxed structure and ensures the outfit loses its formality.
Diana, Princess of Wales, with a printed dress and suede jacket.
Brown suede jackets are one of those garments that resurface every autumn and that work especially well with printed dresses, midi skirts, and denim jeans. Their warm color allows pairing them with creams, greens, burgundies and even blues.
