We've got a theory that every denim designer right now has a Princess Diana mood board taped to a wall somewhere. This is because every trend dominating runways and stores right now [1], from mom jeans to dungarees, was first worn by the lady of denim herself. Showcasing her love for the fabric, Diana would often opt for a pair of high-waisted jeans on an off-duty day with her sons, later dressing up the style on tours with oversize blazers and boots. Along with classic jeans, her closet featured a selection of denim shirts, even styled with jeans for a full Canadian Tuxedo on occasion.
This isn't the first time we've acknowledged Diana's outfits being ahead of their time [2]. Her undeniably iconic style still reigns today, from her love of heavy aviator sunglasses [3] that suited her delicate features to her collection of Summer swimsuits [4] that we're all still shopping right now. (Oh, and hell yes she owned Superga sneakers [5], worn with jeans, of course.) Scroll to be schooled on how to wear denim now, by someone who was styling it royally well 25 years ago.
Dungarees
An appreciator of both comfort and style, Diana had a penchant for denim dungarees in a selection of colours and styles. Here, she poses gleefully against a sundial in a laid back pastel ensemble, styling white denim with loafers and a tailored pink shirt.
Playing with Prince William at a polo match, Diana donned light blue denim dungarees featuring white straps, paired with a white buttoned tee and loafers.
Dungarees were a go-to choice for Diana when attending polo matches. On this occasion, she styled a lemon-yellow pair with a floral shirt, a quilted floral day bag, and red espadrilles.
Classic Jeans Dressed Up
Diana's collection of denim jeans was undeniably classic. While attending a polo match, she styled an acid wash style with brown leather boots, a charity sweater, and an oversize blazer for a relaxed, yet chic look.
While making a speech in Angola, Diana styled a pair of light blue jeans with a double-breasted blazer and her Superga sneakers [6].
While visiting her brother Charles Althorp's newborn baby at the hospital, Diana chose dark denim mom jeans. She styled them with an oversize blazer, tie, and belt — all featuring a gold elephant print.
Denim Shirts
On her trip to Angola, Diana styled a sleeveless denim shirt with high-waisted cropped trousers and loafers for an understated look.
Diana's love of denim shirts matched her love of florals. Here, she wears a relaxed long-sleeved style with a knee-length floral skirt, finished with floral pumps.
Off-Duty Denim
In true '90s mom fashion, Diana often opted for denim when spending time with her two sons. When taking Prince William to school, she styled a star-printed tee with mom jeans and denim pumps.
Spending the day with her sons at Thorpe Park, Diana's throw-on style included dark denim jeans, a green knitted jumper, and an enviable Hard Rock cafe leather bomber jacket.
Making a case for the baseball jacket while on a school run with Prince Harry, Diana styled the look with denim jeans, featuring pocket detailing and brown boots.
Canadian Tuxedo
Proving she truly was the lady of denim, Diana styled a denim shirt with high-waisted jeans while on a skiing holiday — complete with padded boots and a black bomber jacket.