Princess Diana bestowed the world with many gifts. A lifetime of activism and kindness, for one thing; her sons, Princes William and Harry, another. For those with a love of fashion, however, the late royal left behind something else entirely: a sartorial legacy the likes of which the world had never seen.
With a storied penchant for tailored designs with sharp angles, unexpected shapes, and bold, often contrasting colors and prints, the people's princess made her mark on the industry, championing young designers in Britain, like Catherine Walker and Bruce Oldfield, all the while. While's it's a nearly Herculean task to try and declare any one outfit as the most iconic Princess Diana fashion moment of all time, we've narrowed it down to 32, scouring the photo archives for her very best looks.
From her preppy chic pedal pushers and low-top sneakers to the drama-filled, puff-sleeved wedding gown she wore down the aisle, here are Lady Di's biggest style wins.
At just 19 years old, the teen was already two steps ahead of the fads—her purple sweater vest would fit right in as a trending look for 2022!
Fair Isle Fantasy
The public really started to get a feel for Diana's campy sense of style in May 1981, when she accompanied her then-fiancé, Prince Charles, to Balmoral Castle in Scotland. Lady Di wore a neon fair isle sweater, green corduroy trousers, and tall Hunter boots—all of which made quite the sartorial splash.
Prim and Proper
Trading in her wellies for a pair of dainty heels and her bold jumper for a printed mockneck frock, Lady Diana Spencer proved she had plenty of range when it came to fashion in this patterned dress and matching oversized hat at a wedding in London.
A Gown for the Ages
On July 29, 1981, Princess Diana walked down the aisle of St. Paul's Cathedral to marry Prince Charles in a custom design by David and Elizabeth Emanuel, which she paired with her own family Spencer tiara. Made of silk and taffeta with hand-sewn mother-of-pearl sequins and roughly 10,000 pearls, its pièce de résistance was the 25-foot train featuring Queen Mary's lace.
As David would later tell British Vogue, "It was all about drama and making Diana a fairytale princess. The gown was typical of early '80s style—overblown, romantic, flouncy—but we had to get it right because we knew it would go down in history." Mission, accomplished!
The newly married pair returned to Balmoral Castle for their honeymoon, and the royal was dressed for the occasion in a chic loose-fitting jacket and skirt set by Bill Pashley that draped gorgeously against her lithe frame.
The princess showed off her sartorial prowess in this artsy frock by Bruce Oldfield. Between its off-the-shoulder neckline, head-turning print, and floor-skimming silhouette, it was plenty avant-garde, unlocking a new level in Diana's style journey.
Fit for a Princess
Talk about a Cinderella moment! The newly crowned princess wasted no time slipping into her new fairytale digs, including the full-skirted, iridescent Bellville Sassoon she wore to the Victoria & Albert Museum in November 1981.
Donald Campbell was behind the hot pink masterpiece the royal stepped out in April 1983 during a visit to Perth, Australia. The bright number seemed to match her sunny outlook as she waved to the public.
Pretty in Pink
The royal stole the show in the saccharine Victor Edelstein gown she wore for a state reception in Brisbane, Australia. The pink dress created the perfect backdrop to the sparkling sapphire jewels she received as a gift from the Crown Prince of Saudi Arabia.
Princess Diana busted out the family jewels once more at a dinner in New Brunswick, Canada. This time, she paired them with a ruffled Bruce Oldfield frock that came complete with a tiered bottom and ruffled sleeves.
Diana had us seeing spots in April 1983 when she attended the opening of Bourke Street Mall in Melbourne, Australia, in a kitschy suit dress by London transplant Catherine Walker.
The princess looked every bit the lady while attending a match at the Guards Polo Club in 1983, but her Muir and Osborne sweater featuring a "black sheep" still hinted at her cheeky personality.
It's All in the Details
The princess had some fun with the puff sleeves of this striking top at a polo match in Cirencester that August.
Going for Bold
Never one to shy away from a fashion risk, Diana went for the gusto in May 1985 when she hit the streets of Venice, Italy, in this oversized getup by the Emanuels.
The boxy square shoulder pads of this Bruce Oldfield gown served to create a unique, architectural shape that proved Diana was no one trick style pony.
Work of Art
Princess Diana never met an oversized lapel she didn't like, and the stylish masterpiece she donned for a visit to the National Gallery of Art on November 10, 1985 was picture proof. She paired the exquisite outfit, designed by Catherine Walker and Frederick Fox, with a matching hat from her iconic headpiece collection.
There was plenty of fanfare surrounding the Catherine Walker creation the mother of two stepped out in in December 1985, and it's not hard to figure out why. The strapless black-and-white gown was positively stunning!
The activist epitomized après-ski chic in her Head skisuit and accompanying headband while hitting the trails in Switzerland in February 1986.
Diana let down her hair in the Highgrove countryside in July of 1986, embracing a more wholesome aesthetic in a pair of gingham pedal pushers, white low-top sneakers, and a bright pink jumper.
Sure, this purple creation is a dead giveaway of the era with its dropped, ruffle skirt and crushed velvet bodice, but Diana milked it for all it was worth at the Munich Opera House in Germany, adding in long gloves and a simple choker.
Blue Jean Queen
Leave it to the people's princess to make blue jeans high fashion! With a little help from some mid-calf boots, a smart blazer, and a slouchy sweatshirt, Diana was able to take denim to new heights while hitting up the Guards Polo Club in May 1988.
The Look of Love
Diana opted for the color of passion while dining in the city of love on November 10, 1988, in a one-shouldered floral Catherine Walker gown with a voluminous ballgown skirt.
Diana had a knack for expertly tailored suits, and this pink-and-red Catherine Walker number was a prime example.
Also from Catherine Walker was this color-blocked power suit in unexpected hues, which Diana effortlessly put on full display in Hong Kong on November 7, 1989.
Popping Her Collar
Known as the "Elvis dress" for its standing collar, the Catherine Walker two-piece that Lady Di wore in Hong Kong featured sequin and pearl embroidery, and helped her to cement her growing status as fashion royalty. She accessorized it with the Cambridge Lover's Knot tiara.
They say revenge is a dish best served cold, and if anyone ever doubted that statement, they only need to take one glimpse at this Christina Stambolian LBD. Diana absolutely slayed in the sexy dress on June 29, 1994, following her estranged husband's confessions of adultery in a tell-all interview that same night.
Diana was a vision in her signature royal blue hue and a slicked-back 'do while attending the Council of Fashion Designers of America Gala Ball in New York in 1995.
Back to Basics
This black-and-white Tomasz Starsewski number and Philip Somerville hat was reminiscent of the fashions Diana wore in her earlier days on the style scene—only elevated.
While Diana's gowns were undoubtedly iconic, she also knew how to serve up a sporty chic street style moment, as evidenced by her Virgin Atlantic sweatshirt and neon orange bike short combo in London in 1995.
Lady in Red
One of our favorite looks of the bunch was this Catherine Walker halter-style getup, which the blonde beauty dined in while overseas in Argentina.
If the striking hue of this body-skimming piece Diana debuted at the Victor Chang Cardiac Research Institute dinner dance in October 1996 didn't reel you in, the fashion-forward neckline was sure to.
Short and Sweet
The people's princess stunned in an icy blue mini dress that showed off her toned physique for one of her last public appearances at the English National Ballet's rendition of "Swan Lake" in June 1997. Designed by Jacques Azaguy, the piece paired perfectly with her diamond-and-pearl jewels, on loan from Garrard the Jewellers.