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Home»News»The stories behind fashion’s most famous dresses (number 4 actually changed the internet)

The stories behind fashion’s most famous dresses (number 4 actually changed the internet)

  • September 15, 2026
  • Michelle Rowley

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TV, film and celebrity fashion history is woven with unforgettable garments and iconic looks that have shaped culture for decades.
Audrey Hepburn in her iconic little black dress in Breakfast at Tiffany's

Michelle Rowley explores 12 infamous looks that have left a lasting impression.

TV, film and celebrity fashion history is woven with unforgettable dresses – garments that defined eras, symbolised cultural shifts, and left lasting impressions on the red carpet and beyond. From Audrey Hepburn’s chic black Givenchy dress in Breakfast at Tiffany’s to Jennifer Lopez’s plunging green Versace gown, these iconic pieces continue to inspire designers and makers today.

Whilst there’s some celebrity dresses you probably wouldn’t want to recreate (Lady Gaga’s meat dress anyone?), we take a look at some of the stars’ best loved looks.

Marilyn Monroe wore the ‘Happy Birthday, Mr. President’ dress in 1962
Photo: Getty/Bettmann

Marilyn Monroe (and Kim Kardashian!)

When Marilyn Monroe wore the ‘Happy Birthday, Mr. President’ dress in 1962, it became an instant sensation. Designed by Jean Louis, the sheer, form-fitting gown, embellished with 2,500 crystals, scandalised and mesmerised audiences when Monroe wore it to breathlessly serenade JFK. Its bold, sultry design symbolised Monroe’s allure and cemented her status as a cultural icon, forever linking fashion with political history. Whilst Kim Kardashian’s attention-grabbing decision to wear the dress to the 2022 Met Gala sparked controversy, it reaffirmed the dress’s legendary status in popular culture.

Audrey Hepburn in her iconic little black dress in Breakfast at Tiffany's
Photo: Getty/Donaldson Collection

Audrey Hepburn’s LBD

The long-standing collaboration between Audrey Hepburn and the designer Hubert de Givenchy is legendary, with the looks they created together leaving an impact on the world of film and fashion. They carefully crafted designs that suited Hepburn’s simple and understated look, such as that floor-length satin black dress for her character Holly Golightly in the 1961 film Breakfast at Tiffany’s. Even if you have not watched the film, you’ve certainly seen the dress. The gown defined chic sophistication and popularised the little black dress (LBD) as an essential wardrobe staple for generations to come.

Kate Middleton wearing a blue wrap dress at her engagement announcement to HRH Prince William in 2010
Photo: Getty/Chris Jackson Collection

Kate Middleton blue wrap dress

When Kate Middleton (HRH Princess of Wales) wore a blue wrap dress by Issa to announce her engagement to Prince William in 2010, it sparked a fashion frenzy. With the elegant silk jersey dress beautifully matching her sapphire engagement ring, the iconic dress cemented the beginning of her long-standing influence on fashion.

Jennifer Lopez wearing her iconic revealing green chiffon dress worn at the 2000 Grammys
Photo: Getty/Scott Gries

Jennifer Lopez at the 2000 Grammys

Jennifer Lopez’s iconic revealing green chiffon dress worn at the 2000 Grammys, was a daring, tropical-inspired piece with a deep, plunging neckline and flowing sheer fabric. Designed by Donatella Versace, it revolutionised red-carpet fashion and Lopez called it “my biggest fashion moment ever.” Incredibly, the massive public interest in the dress was the motivation for Google’s president Eric Schmidt to create Google Images!

Princess Diana arriving at a Vanity Fair party in a slinky black off-the-shoulder Christina Stambolian dress
Photo: Getty/Anwar Hussein

Princess Diana’s ‘revenge dress’

On the very night Prince Charles, now King Charles III, admitted to adultery in a televised documentary, Diana arrived at a Vanity Fair party in a slinky black off-the-shoulder Christina Stambolian dress. It was a bold departure from the modest silhouettes typically expected of royal women and instantly dominated newspaper front pages the next day, coined since as the ‘revenge dress’. The look signalled a new chapter for Diana: confident, independent and firmly in control of her own narrative.

Claire Danes’ wearing an iconic white pleated angel dress in Baz Luhrmann’s 1996 adaptation of William Shakespeare's Romeo + Juliet
Photo: Getty/20th Century Fox

Clare Danes in Romeo + Juliet

Claire Danes’ white pleated angel dress in Baz Luhrmann’s 1996 adaptation of William Shakespeare’s Romeo + Juliet symbolised purity and ethereal beauty. Featuring soft pleats, a fitted bodice (and all-important wings!), it enhanced Juliet’s innocence and left a lasting influence on romantic fashion trends.

Megan Markle wearing a Stella McCartney halter neck dress for the evening reception of her wedding
Photo: Getty/WPA Pool

Meghan Markle’s wedding attire

Although Meghan Markle’s (Duchess of Sussex) Givenchy boat neck wedding dress was the epitome of simple sophistication, we’re might struggle for an occasion to wear something similar. The stunning Stella McCartney halter neck dress she wore for the evening reception, which was still seen by millions, is however something we could get on board with. The sleek silk crepe, floor-length dress complemented her minimalist bridal style and made it an instant fashion hit.

Liz Hurley wearing a black Versace gown, held together by oversized gold safety pins
Photo: Getty/Comic Relief

Liz Hurley’s safety pin dress

Before attending the premiere of Four Weddings and a Funeral with Hugh Grant, Elizabeth Hurley was relatively unknown outside fashion circles. Her black Versace gown, held together by oversized gold safety pins, instantly made her one of the most photographed women in the world. Equal parts glamorous and provocative, the dress became a defining image of the 1990s and helped establish Versace as the decade’s master of red-carpet spectacle.

love the ‘polo scene’ dress worn by Julia Roberts’ in the 1996 film Pretty Woman
Photo: Getty/Hulton Archive

Julia Roberts in Pretty Woman

Who doesn’t love the ‘polo scene’ dress worn by Julia Roberts’ in the 1996 film Pretty Woman? Designed by Marilyn Vance, the belted brown and white polka dot midi dress exuded classic elegance and cemented its status as an iconic cinematic look.

Marilyn Monroe’s white halter neck dress catching in an updraft over a subway grate in the 1955 film The Seven Year Itch
Photo: Getty/Bettmann

Marilyn Monroe’s halter neck

An unforgettable cinematic moment was born when Marilyn Monroe’s white halter neck dress was caught in an updraft over a subway grate in the 1955 film The Seven Year Itch. Designed by William Travilla, the dress – with its billowing pleated skirt – symbolised Hollywood glamour and cemented Monroe’s bombshell image. The scene became legendary, influencing fashion, pop culture, and advertising, making the dress one of history’s most recognisable garments.

Cher arriving at the Academy Awards in a barely-there black Bob Mackie creation complete with a dramatic feathered headdress
Photo: Getty/Bettmann

Cher’s Bob Mackie Oscar dress

Arriving at the Academy Awards in a barely-there black Bob Mackie creation complete with a dramatic feathered headdress, Cher turned the red carpet into theatre. The look challenged Hollywood’s unwritten rules about how leading ladies should dress and cemented her reputation as fashion’s ultimate risk-taker. While some critics were scandalised at the time, the outfit is now regarded as one of the most influential red-carpet looks ever worn.

Emma Stone, Writer/Director Damien Chazelle and Ryan Gosling at Summit Entertainment for the premiere of La La Land
Credit: Getty/Eric Charbonneau

Emma Stone in La La Land

Emma Stone’s Mary Zophres’ bright yellow dress in La La Land captivated audiences, becoming an instant icon of cinematic fashion. Its vintage-inspired silhouette, delicate floral pattern, and twirling movement enhanced Mia’s dreamy, hopeful character, whilst the bold yellow left a luminous presence in the film’s nostalgic aesthetic.

Michelle Rowley

Michelle Rowley

Michelle Rowley is a content writer and dressmaking tutor with a love of fashion history who regularly writes for Simply Sewing. Follow her on social media via @stitchywhitney.

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