Playing Princess Di | Recreate 12 Of Diana’s Most Iconic Looks

Imagine today with the late Princess Diana to guide our way? “The People’s Princess,” Diana’s legacy will forever be synonymous with divinity, encapsulating all the good this world has to offer. Not the least of which the fashion world.

I remember being young and idolizing Princess Diana, not for her royal status, but for her charisma. She was everything you’d want in a role model: kind, good, beautiful, loving, philanthropic, and independent. Diana was as close to a living deity as this world has ever known. And for that reason, the world went dark on the night of her tragic passing in Paris over twenty years ago. Diana’s death dimmed not only the UK and The City of Lights; the entire planet has been little less bright without her. That being so, Diana’s legacy lives on: in her sons, in her charities, in her spirit, and yes, even in her fashion.

Mother. Humanitarian. Friend. Princess. Rebel. The least of Diana’s titles might be Fashion Icon, but that’s a testament to the woman she was, not her taste level. From a fashion standpoint, I would say Diana was infallible. She made choices that pushed boundaries and proved time and time again she played by her own set of rules.

From THE wedding dress to THE little black revenge dress, Diana’s influence on the world of fashion is unmatched. For context, I wanted to do this post because as a child Diana was IT for me. I wanted to be “like Princess Diana” when I grew up, then eventually I realized the closest I would get to “Playing Princess Di” would be her attire. As I tried to recreate her most memorable looks I kept uncovering more inspiring options so I assure you, I know the following list is not comprehensive. Finally I landed on the 12 looks below, but I’ve taken some liberties. While reimagining these styles I’ve broken some fashion rules, just as Diana did on many occasions, but I think you’ll find the essence of the Princess in each of these options.

“I don’t go by the rule book; I lead from the heart,
not the head.” – Princess Diana


DECEMBER, 1981 – LONDON
V&A Museum attending the ‘Splendours of the Gonzagas’ exhibition
Designed by Bellville Sassoon
REIMAGINED
Giambattista Valli Puff-sleeved floral-print georgette gown
Cost: $3,206

JUNE, 1983 – LONDON
UK premiere of James Bond film Octopussy at Odeon Leicester Square
REIMAGINED
Option 1. Marchesa Notte one shoulder beaded long dress
Cost: $477
Option 2. Rachel Zoe Arielle One Shoulder Metallic Pleated Maxi Dress
Cost: $595

AUGUST, 1983 – UK
Polo Match
REIMAGINED
REISS March Printed Wrap Blouse
Cost: $120
Frame Denim Mini Skirt
Cost: $195
Isabel Marant Lecce leather belt
Cost: $160

(Off-White has a GREAT iteration of the original blouse so if you can find it on a resale site you might be able to nail this exact look.)

DECEMBER, 1984 – LONDON
Wearing a shimmering sequin maxi dress for an evening event in London
REIMAGINED
Le Kasha Silk-satin midi skirt
Cost: $392
Vince Ribbed cashmere sweater
Cost: $177
BHLDN Simply Silk Sash
Cost: $60

NOVEMBER, 1985 – WASHINGTON, DC
White House dinner held by President Reagan
Designed by Victor Edelstein

REIMAGINED
Talbot RunhofStretch-Velvet Off-Shoulder Short-Sleeve Mermaid Gown
Cost: $1,109.40
Angara 18″ Graduated Freshwater Pearl Triple Strand
Cost: $899

APRIL, 1989 – LONDON
REIMAGINED
18000 Gildan Heavy Blend™ Adult Crewneck Sweatshirt
Cost: Varies
Gildan Ladies’ Open Bottom Pocketed Sweatpant
Cost: Varies
Polo Ralph Lauren Men’s Nautical Chino Ball Cap
Cost: $55
RE/DONE 70s double-breasted pinstriped wool blazer
Cost: $525
Off-White For Walking cowboy boots
Cost: $1,005

JUNE, 1994 – LONDON
“Revenge Dress”- Vanity Fair Party at the Serpentine Gallery
Designed by Christina Stambolian
REMINAGED
Cushnie Asymmetrical-Neck Slip Dress with Cascading Skirt
Cost: $1,017

(Reimagined it may not be THE little black dress, but it’s a midnight blue dress that has a sexy revenge vibe and pulls in the necklace without her trademark, hard to pull off pearls.)

SEPTEMBER, 1995 – MODENA
Children of Bosnia charity concert
Designed by Versace
REIMAGINED
Option 1. Paco Rabanne Fringed-paillette chainmail mini dress
Cost: $2,304
Option 2. Paco Rabanne embellished mini dress
Cost: $1,991

(I’m not sure why I went the Paco Rabanne route but something about the shape reminded me of this Versace classic, just with a rebellious spin.)

JUNE, 1995 – LONDON
Vanity Fair Party at the Serpentine Gallery
Designed by Catherine Walker
REIMAGINED
Jacquemus Cortese Dress
Cost: $766.50

1995 – LONDON
REIMAGINED
Fly Virgin Atlantic Pinup Sweatshirt
Cost: $29.99
ban.do High Rise Bike Short – Sherbet
Cost: $48

1996 – AUSTRALIA
Opening the Victor Chang Cardiac Research Institute
REIMAGINED
Bec & Bridge Frederic Asymmetrical Midi Dress
Cost: $250

It’s only fitting the final look is immortalized as one of the most memorable and photographed trips of the 20th century

1997 – ANGOLA
Humanitarian work with The Halo Trust
REIMAGINED
Eddie Bauer Girl On The Go Sleeveless Shirt
Cost: $42
Eddie Bauer Aspire Ankle Pants
Cost: $27.50
TOMS Alpargata Slip-On
Cost: $55.99
Saint Laurent Square-frame acetate sunglasses
Cost: $270

“I think the biggest disease the world suffers from in this day and age is the disease of people feeling unloved. I know that I can give love for a minute, for half an hour, for a day, for a month, but I can give. I am very happy to do that, I want to do that.” – Princess Diana

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