June 17, 2024

42 of Princess Diana’s most iconic looks from her inimitably chic wardrobe

The Dress: Valued in 1981 at £9,000, Lady Diana Spencer’s antique lace wedding dress was complete with a 25-foot train of ivory silk taffeta. It was one of the most guarded secrets in fashion history, only to be matched by the hushed privacy surrounding Kate Middleton’s stunning Alexander McQueen wedding dress.

The Occasion: The wedding of Lady Diana and Charles, Prince of Wales on 29th of July, 1981.

Why We Love It: Designed by Elizabeth Emanuel, the dress captures the very extravagance of the Eighties era. This frock was not attempting a fashion understatement.

The Dress: A respectable high-neck and long-sleeved maxi dress in silk.
The Occasion: A Royal family occasion, for the wedding of Nicholas Soames.
Why We Love It: There’s nothing quite like matching accessories and a stunning piece of millinery to set a fashion-loving nation’s hearts alight!

The Dress: At 9 months pregnant, a 20-year-old Diana rewrote the palace rules on maternity wear and opted for elegant comfort, rather than restrictive formal attire.
The Occasion: This slouchy pink number was a breezy choice for perusing the flash cars at the polo.
Why We Love It: The young princess didn’t fall afoul to the global spotlight and kept her priorities in place. Feel good. Look fabulous. Here, here!

The Dress: A V-neck, polka-dot blouse dress, paired with preppy pumps. A natural parallel can be drawn here with the spotty Jenny Packham dress that Kate Middleton wore when leaving the very same hospital with the latest Royal babe.
The Occasion: The paparazzi’s first glimpse at the new royal parents and the swaddled babe, Prince William, outside St Mary’s Hospital.
Why We Love It: It’s practical chic and that nautical neckline is still bang-on trend.

The Dress: This Bruce Oldfield midnight blue dress caused a frenzy amongst the fashion press. The Princess startled her critics by stepping out in a dramatic dress that moved around her slender frame, mere months after giving birth.
The Occasion: Diana attends a banquet in Guildhall, London in November, 1982.
Why We Love It: The drama of the asymmetric shoulder and the perfect match of accessories – what’s not to adore? !

The Dress: A white asymmetric gown covered in silver bugle beads by Hachi. This dress raised over £60,000 at a Christie’s auction.
The Occasion: Octopussy, the James Bond premiere in June, 1983.
Why We Love It: The Royal outshone all the stars on the red carpet in a contemporary cocktail number that would score style points today.

The Dress: This sparkling red evening gown was a custom-made creation by one of her long-standing favourite designers, Bruce Oldfield.
The Occasion: A black-tie dance.
Why We Love It: It’s the archetypal ‘princess’ shape – a frou frou skirt and the ever-important cinched-in waist.

The Dress: An Emanuel sparkling turquoise dress.
The Occasion: A black tie dance on the Royal tour of Australia, spring 1983.
Why We Love It: While the frock is fabulous enough, we love the dare-devil addition of diamonds and emeralds (here, her necklace is worn as a headband).

The Dress: The long hemlines of the 1983 Australia tour continue, this time in pink and complete with a rather reserved matching jacket.
The Occasion: A formal procession.
Why We Love It: The Princess looks like the epitome of an English Rose in that pastel hue. Pout not included.

The Dress: A reserved, polka-dot silk summer frock. This certainly falls under the ‘casual smart’ category, in royal terms.
The Occasion: An official visit to New Zealand, 1983.
Why We Love It: On many this midi dress could look apologetic but Diana pulled it off with her signature panache.

The Dress: The bright pink, silk evening gown that received rave reviews from the global press. ‘Pretty in pink’, they declared!
The Occasion: 1983’s official visit to Brisbane, Australia.
Why We Love It: Few can pull off such a shade of pink without looking like Barbie. Of course, for Lady Diana this is a fashion thumbs up rather than a faux pas.

The Dress: A floor-length peach sparkling dress. On paper? Terrible. On Diana? Fabulous!
The Occasion: The Starlight Express London premiere, 1984.
Why We Love It: Diana recycles her fashion accessories – note the new spin on her metallic clutch and court shoes combination.

The Dress: Another Bruce Oldfield power dress – in red and complete with a slash-neck and in-built shoulder pads.
The Occasion: A Royal visit to Melbourne, Australia in 1985.
Why We Love It: This silhouette is style perfection.

The Dress: More polka-dots for the Princess but this time, worn with a loose coat and accessories that hark to Julia Roberts in Pretty Woman.
The Occasion: A Youth Rally visit in Wales, 1985.
Why We Love It: As she was prompted by the palace to wear a selection of British designers, Diana enjoyed collaborating and making her outfits lively.

The Dress: The stunning midnight blue Victor Edelstein evening gown.
The Occasion: The White House State dinner, given by President and Mrs Reagan in November 1985, in which the Princess memorably danced with John Travolta.
Why We Love It: This dress is still making headlines! In March 2013, at the Kerry Taylor Auction in London a man who wanted to ‘cheer up’ his wife bought it for £240,000.

The Dress: The gold lame Bruce Oldfield dress that wowed the world.
The Occasion: A View To A Kill, James Bond premiere in 1985.
Why We Love It: This is what an iconic fashion moment looks like. Marilyn who?

The Dress: The Catherine Walker green sequin dress that was auctioned in 2013 for over £170,000.
The Occasion: Arriving at The Royal Lancaster Hotel in London for a charity benefit.
Why We Love It: It’s one of the Princess’ most talked about outfits thanks to the thigh-baring split and swooping neckline.

The Dress: Another Bruce Oldfield fashion DO worn by the Princess.
The Occasion: America’s Cup Ball, 1986.
Why We Love It: Rather than buckle under the pressure of what to wear on another royal outing, the Princess upped the ante with a bare décolletage, demure long evening gloves and a tulle skirt that would have made any Eighties power dresser nervous!

The Dress: Formal and chic rolled into one frock, Catherine Walker custom-made this dress for Diana.
The Occasion: The royal tour of the Gulf states in Saudi Arabi, 1986.
Why We Love It: The monochrome sash relates to the classic heritage of the British monarchy. P. S. All salute the impressive shoulder padding.

The Dress: No, it’s not a wedding dress but rather a stately gown for a black-tie ball. Lace, silk and a tiara make this a ubiquitous style moment.
The Occasion: A formal dinner at the British Embassy in America, 1986.
Why We Love It: This number stays on the right side of the Eighties.

The Dress: Famously inspired by Grace Kelly, this Catherine Walker dress lit up the Cannes red carpet.
The Occasion: The Cannes Film Festival, 1987.
Why We Love It: In a recent auction it raised over $70,000, proving its status as a museum-worthy gown to be remembered.

The Dress: Diana swapped polka-dot for stripes, and relaxed in this look.
The Occasion: A trip to Australia, 1988.
Why We Love It: This rather worn phrase springs to mind: a smile is the world’s greatest accessory. Fact.

The Dress: Dubbed the ‘Elvis Dress’ by harsher members of the British press, the Princess’ Catherine Walker dress set tongues wagging.
The Occasion: A tour in Hong Kong, 1989.
Why We Love It: We DO adore a frock that whips up some controversy.

The Dress: Who else but Bruce Oldfield could dress Lady Diana in head-to-toe sparkly red and make it look good?
The Occasion: A banquet held in Claridges, London in 1989.
Why We Love It: Full marks for fashion bravery. We can’t think of a current celeb who could pull off this number.

The Dress: The bois de rose taffeta strapless dress by Catherine Walker. It raised $50,000 in an auction.
The Occasion: When The Whales Came, film premiere in 1989.
Why We Love It: A pretty print doesn’t always offset a sassy fitted look. This frock may have pushed the parameters of what the Buckingham Palace style guide allowed.

The Dress: Another favourite from Catherine Walker. Yes, it’s modest but oh-so stunning.
The Occasion: A royal visit to Kuwait, 1989.
Why We Love It: This dress is like a Mary Katrantzou creation, on ice.

The Dress: Well guessed, yet another creation by Catherine Walker. Naturally, for a public figure such as Diana, many of her outfits needed to be planned ahead and custom-made to hug each curve.
The Occasion: A concert at the Royal Albert Hall, 1990.
Why We Love It: This look proves that formal can also be fun.

The Dress: A fitted bodice dress complete in a classic floral print. This gown was placed up for auction in March 2013 and raised tens of thousands for its iconic status as a feminine Diana dress.
The Occasion: At a banquet in Brazil, 1991.
Why We Love It: Oh, this reignites the fashion desk’s love of a one-shouldered look.

The Dress: The two little princes may steal the show style-wise but it’s a close contest thanks to Diana’s baroque red and pink cocktail outfit.
The Occasion: The Joy Of The World, Christmas Spectacle at the Royal Albert Hall, 1991.
Why We Love It: Diana certainly knew how to accentuate her assets and often opted for clever necklines and fitted, bespoke tailoring.

The Dress: We hereby mark the beginning of Diana’s mini dress era with this sexy navy blue dress.
The Occasion: A concert at the Royal Albert Hall, 1991.
Why We Love It: The hemline may rest above her knee but this was the beginning of her wardrobe rebellion against her allegedly restrictive style guide.

The Dress: As the Princess dabbled in more off-the-shoulder styles, her hemlines started to climb higher.
The Occasion: Attending a production at the Sadlers Wells theatre, London in 1991.
Why We Love It: Fashion aficionados, meet the perfect black and pink cocktail dress. Sigh.

The Dress: The Spencer family tiara was deftly teamed with this Catherine Walker dress.
The Occasion: The 1991 tour of India.
Why We Love It: This outfit captured the very essence of modern royalty.

The Dress: Still on duty to promote the British fashion industry, the Princess entrusted her favourite designer, Catherine Walker to conjure up another dress that balanced playfulness with a reserved touch.
The Occasion: A film premiere, London 1993.
Why We Love It: A well-appointed off-the-shoulder dress will always win our hearts.

The Dress: Known by press as the ‘revenge’ dress, designed by Christina Stambolian. At this stage various scandalous books and tapes had been published. And so, the fashion rebellion truly began…
The Occasion: At the Serpentine Gallery in summer 1994.
Why We Love It: This is the LBD that speaks a thousand words. It has since been auctioned for $74,000.

The Dress: As the pressure to wear mainly British deisgners lifted off of Diana’s shoulders, she dabbled with new names such as Jacques Azagury.
The Occasion: On a trip to Venice, 1995.
Why We Love It: A little red dress is the ultimate ‘freedom’ statement.

The Dress: An ice blue, beaded Catherine Walker cocktail dress. It served to prove that she didn’t totally abandon her style roots.
The Occasion: A Vanity Fair party in 1995.
Why We Love It: Her new fashion agenda had been set – the smart micro mini dress overtook her penchant for long and dramatic gowns. This dress has also been auctioned and raised $77,300.

The Dress: The Versace LWD.
The Occasion Children of Bosnia charity concert, Milan 1995.
Why We Love It: Diana was fashion’s darling from the start but outfits like this had her topping Best Dressed lists.

The Dress: A simple Catherine Walker mini dress in classic black.
The Occasion: Apollo 13 premiere in 1995.
Why We Love It: Diana worked the all-time classic combination of pearls, LBD and red nail varnish to perfection.

The Dress: Wearing Ralph Lauren with Ralph Lauren.
The Occasion: A White House dinner in Washington, 1996.
Why We Love It: It was a high society moment, darlings.

The Dress: Taking a fashion vacation from mini dresses, Diana wore a striking purple evening dress by Versace with pearls and her iconic sapphire ring.
The Occasion: Field Museum in Chicago, 1996.
Why We Love It: It was a timeless Gianni Versace creation worn by a national treasure. Plus, there’s some seriously good accessorising going on here.

The Dress: A Dior evening gown.
The Occasion: Dior’s 50th Anniversary in New York, 1996.
Why We Love It: It was such a nonchalant look and an early contender for the underwear-as-outerwear trend.

The Dress: An effortless orange shift dress.
The Occasion: On a visit to Northwick Park Hospital, 1997.
Why We Love It: Bright, chic and sexy rolled into one.

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