The 20 Most Unforgettable Dresses of the Past Century


There are dresses, and then there are dresses. They are the ones forever etched in our collective fashion consciousness as that LBD, that wedding dress, or that cut-down-to-there evening gown. They require very little, to no introduction, but they have cemented sartorial reputations, built empires, and made red carpet dreams come true. Gorgeous in form, and sometimes ahead of their time, they are not just beautiful but have that intangible je ne sais quoi that make the true star—its wearer—shine. Here, Town and Country takes a look at some of the most memorable frocks that have in many ways, shaped fashion history.  

Most Memorable Wedding Gowns

There’s no wedding gown quite like a royal wedding gown, and through the years these ivory confections have captured the hearts of millions. The designs and the lucky fashion designers who were to make them remained closely guarded secrets until the big day. Here we reminisce on the pomp and pageantry for when royalty says ‘I Do’.

1. Princess Diana’s Wedding Gown

The wedding gown worn by Lady Diana Spencer to wed Prince Charles was one the world held its breath for, with 750 million people tuning in to the broadcast in July 1981. Made of ivory taffeta and antique lace, the gown’s 25-foot train and 153-yard tulle veil made quite an entrance as Diana walked down the aisle of St. Paul’s Cathedral. It was designed by British designers David and Elizabeth Emanuel, who even had to install a safe at their atelier just to keep the dress and any sketches related to it under wraps. It still remains one of the most iconic wedding gowns to this day, and a beautiful reminder of the pure, innocent beauty of the beloved ‘People’s Princess’.


2. Kate Middleton’s Wedding Gown

The romance between Prince William and college sweetheart Kate Middleton was one the public watched with a lot of eagerness and fascination, culminating in an absolute frenzy right before their wedding. It was obviously going to be a grand affair, but what people were really excited about was Kate’s bridal ensemble. And clad in an ivory lace ballgown by Sarah Burton for the house of Alexander McQueen, she did not disappoint. It combined royal tradition with modernity, which resulted in a classic design that paid homage to traditional English techniques and needlework, while still managing to be fresh. Oozing femininity, with subtle hints of grandeur, this was how you marry a prince. 

3. Grace Kelly’s Wedding Gown

She was the golden girl of the silver screen, while he was one of the most eligible bachelors in Europe. Needless to say, the April 1956 wedding of Grace Kelly to Prince Rainier III of Monaco was the real-life fairytale the world couldn’t get enough of. Her wedding gown, crafted by Metro-Goldwyn-Mayer’s costume designer Helen Rose, was a gift from the studio. The elegant piece featured antique rose point lace that was formed into an elegant high neckline and long sleeves. The silk cummerbund accented the actress’ 21-inch waist, and was finished off with a full peau de soie skirt. It remains as beautiful today as it did then, and has surely inspired many a bride with its timeless romance.  

4. Meghan Markle’s Wedding Gown

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Created by British designer Claire Wright Keller for the House of Givenchy, Meghan Markle’s minimalist gown was quite a departure from the traditional look associated with royal weddings. Featuring an open bateau neckline, three-quarter-length sleeves, and a relaxed shape, it gave off a very understated elegance that put the focus solely on the bride. The dress was finished off with a five-meter-long veil that took embroiderers 500 hours to make and featured the distinct flora of the 53 Commonwealth countries, of which Her Majesty The Queen is Head, as well as that of her home state of California. As a finishing touch, a piece of the blue dress the Duchess of Sussex had worn to her first date with Prince Harry was also sewn into the gown. 

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Most Memorable Red Carpet Gowns

Beautiful dresses on the world’s most beautiful people, one can’t help but be enthralled by the red carpet. It represents the pinnacle of glamour, when the world’s most famous make their grand entrances to the adulation of fans and the paparazzi. Here, Town and Country ruminates on some of the most breathtaking gowns.

5. Jennifer Lopez’s Green Versace Dress 

Before the ubiquitous naked dress, there was J.Lo and the green Versace gown that shut down the red carpet at the 2000 Grammy’s. With a ravine-deep plunge that went right past her navel, the tropical print concoction was barely held together by a brooch and a lot of double-sided tape. But the singer-slash-actress walked with so much confidence, and an almost girlish charm, that it made wearing such a daring number look absolutely easy-breezy. She didn’t win any awards that night, but her photograph did land in more publications than you can count, and became one of the most talked about dresses in recent history. In fact, it was such a popular search query, that it inspired the founders of Google to come up with Google Images, forever changing how we look for pictures online.

6. Liz Hurley’s Safety Pin Versace Dress

She came as Hugh Grant’s plus one but left a style star all on her own. It was 1994 in London and English actress and model Elizabeth Hurley accompanied her then-boyfriend Grant to the premiere of his hit movie Four Weddings and a Funeral. Clad in a silk crepe Versace dress, with its many slits precariously held together by oversized gold safety pins, she quite literally stole the show. The next day, the press was all over THAT dress, helping make both Liz Hurley and Gianni Versace household names.


7. Gwyneth Paltrow’s Pink Ralph Lauren Dress

She was Hollywood’s darling and she knew it. Fresh her performance in the critically acclaimed film Shakespeare in Love, for which she would win Best Actress, Gwyneth Paltrow owned the 1999 Oscars red carpet in a bubblegum pink taffeta ballgown custom made by Ralph Lauren. It was altogether young and sweet with a ‘pretty in pink’ feel, but exuded a timeless allure that was likened by many to the sophistication of Grace Kelly. Despite its relative simplicity, it is one of those dresses that when worn by the right woman at just the right time make it impossible to forget.

8. Nicole Kidman’s John Galliano Chinoiserie Gown

Nicole had yet to be the legend that she is today, but the then Mrs. Tom Cruise accompanied her husband to the 1997 Academy Awards clad in a slinky chartreuse number, turning heads wherever she went. Designed by John Galliano for the House of Dior, the silk haute couture gown featured intricate floral embroideries and a slit lined with mink. It was a daring choice for the red carpet, but one that worked in everyone’s favor. Galliano was a relative newcomer to the scene and this dress helped validate his new position at Dior, whilst establishing Nicole as a style darling willing to take calculated risks in the name of fashion

9. Halle Berry’s Sheer Floral Elie Saab Gown

Who could forget Halle Berry and her burgundy Elie Saab gown, its sheer illusion bodice decorated with cascading lilies that showed off one of Hollywood’s most enviable figures? Everything about it was just perfect, from the graceful floral embroidery that left just enough to the imagination, to the dramatically draped skirt that complemented the sexy bodice. And of course, there was Halle, whose exuberant sensuality carried off the daring, and artistic gown with aplomb. She would win the Oscar for Best Actress for her performance in Monster’s Ball that night and remains the only African American actress to win that distinction to this day.

10. Julia Roberts’ vintage Valentino Gown

She has worn many beautiful gowns but one many acknowledge as a clear favorite was the vintage Valentino frock she wore to the 2001 Oscars, from the designer’s 1982 Fall Haute Couture collection. The velvet gown, with its white satin lines gracefully flowing through Julia’s figure, created such a striking picture and was gorgeous from all angles. The Erin Brockovich star finished off the look with the best accessory of all, an Academy Award for Best Actress, further adding to legend of this singular moment.

11. Grace Kelly’s Edith Head Gown

Widely regarded as one of the most beautiful Oscars gowns of all time, Grace Kelly’s aquamarine dress continues to captivate with its timeless sophistication. The icy blue sheath had a fitted bodice and a skirt draped with an almost bustle-like finish, and was expertly crafted by legendary costume designer Edith Head. The Hitchcock heroine first wore the gown to the premiere of Country Girl, but also deigned it the perfect outfit to accept her Academy Award for Best Actress in 1955. And to top it all off, she also appeared on the cover of Life magazine, further immortalizing this duchesse satin confection.  


12. Rita Moreno’s Pitoy Moreno Dress

So beautiful, she had to wear it twice! Rita Moreno first wore this gown by National Artist Pitoy Moreno to the Oscars in 1962, in which she won Best Supporting Actress as Anita in West Side Story. Rita had been filming in Manila at around that time, and had asked the designer to make something for her when she had found out that she was nominated. For the 90th Academy Awards, the Puerto Rican actress returned to the red carpet in the same gown (albeit with slight modifications), looking just as fabulous 56 years later. Which just goes to show, great design is truly timeless.

13. Bjork’s Marjan Pejoski Swan Dress

There was a collective gasp of horror heard around the world when Bjork wore her swan dress to the Oscars in 2001, and while wearing it, even pretended to lay a few eggs. The outfit by Marjan Pejoski was basically a full body stocking with a swan draped around the neck, and was widely considered the fashion faux pas of the century. It’s been criticized to no end, and parodied on TV and film more times than we can count. But in a surprising twist of fate, it’s now exhibited at the Met as part of the Costume Institute’s ongoing exhibition as one of the most enduring examples of ‘camp’ in fashion. It did ruffle a few feathers for sure, but in the end, created a pop culture moment we can’t get enough of.

14. Michelle Obama’s Jason Wu Inaugural Dress

“First of all, how good looking is my wife?’ asked the newly minted President of the United States, Barack Obama at the 2009 Inaugural Ball. The man of the hour only had eyes for Michelle Obama, clad in an ivory evening gown embellished with handmade chiffon flowers and Swarovski crystals by emerging designer Jason Wu. This was the first of many times Michelle would use her position to great effect, favoring American brands and young talent for her public appearances. To encapsulate her purpose, FLOTUS’ wardrobe adviser Meredith Koop remarked in an interview with Harper’s Bazaar, "When [the first lady] wears an up-and-coming designer, it creates this feeling that anything is possible.”

Most Memorable Movie Ensembles

Costumes have always been an integral part of the narrative of film and television. They define a character, shape a story, and immortalize a moment. They are the stuff of dreams and when all the elements come together, they become an indelible part of film history.

15. Audrey Hepburn’s Givenchy LBD

When you think of Audrey Hepburn, you think of her as Holly Golightly, in an elegant black dress with a bateau neck, hair perfectly coiffed, holding a croissant and a coffee. She looks impossibly chic and also somehow a bit naïve and lost, as was her persona in the 1961 classic Breakfast at Tiffany’s. That now-iconic dress was a creation of relative newbie Hubert de Givenchy, with whom Hepburn had developed a deep friendship that would span almost four decades. At first, Paramount Pictures was a bit hesitant to have the young Frenchman make Hepburn’s costumes, but she had felt such a connection with the designer that she even agreed to pay for the dresses herself. In the end, that move paid off, and Givenchy’s costumes and dresses for Hepburn have helped define the inimitable style of that era.  


16. Carrie Bradshaw’s Wedding Gown in Sex and the City

We had followed the love story of Carrie, played by Sarah Jessica Parker, and her emotionally unavailable lover Big for many seasons, and we couldn’t wait to see what she’d wear to the wedding. For a woman whose obsession with shoes and idiosyncratic style defined a generation, this was a moment for the books. She wore a satin Vivienne Westwood ballgown accessorized with turquoise feathers in her hair and walked up the hallowed steps of the New York Public Library. With its dramatic draping, the voluminous ballgown was showstopping, eclectic, theatrical and very Carrie. It is unfortunately not the dress to be found in when one is to be stood up at the altar. Eventually, she did find her happily ever after, but that is another dress and another tale for another time.

17. Julia Roberts Red Dress in Pretty Woman

We all love a good romcom, and one with Julia Roberts, Richard Gere, and the magic of the ‘90s is nothing short of incomparable. Roberts who plays Hollywood working girl Vivian Ward, meets wealthy businessman Edward Lewis, played by Gere in the classic film Pretty Woman. The two fall madly in love, and in one crucial scene, Roberts appears in the most elegant scarlet gown by designer Marilyn Vance-Straker. Part of its allure is that the dress hints at an inward change in Roberts. When we first met her, she had on a blonde wig and the most street-wise mini dress one can imagine. Seeing her swathed in elegance, perhaps marks the beginning of Ward wanting more for her life and knowing that she deserves it. We all know how the story ends, but can we just say, how’s that for a makeover?

18. Marilyn Monroe’s White Dress


A gust of wind, a little white dress, and America’s goddess, all came together to create one of the most unforgettable moments in film history. It was in 1954 while filming The Seven Year Itch when Marilyn Monroe giggled atop one of New York’s subway grates, deftly holding down her pleated frock as the subway whizzed by underneath. It was a dress and a moment emblematic of the Hollywood star, evoking equal parts sensuality and innocence. Concocted by costume designer William Travilla, who also worked on Monroe’s dresses for Gentlemen Prefer Blondes, the white halter was sold at auction in 2011 for 5.6 million dollars.

19. Cinderella’s Blue Ballgown


This was the princess dress to rival all princess dresses, with generations of young girls growing up to this image of Cinderella in the blue gown she wore to the ball. For Disney’s live-action remake, her fairy godmother was none other than Oscar-winning costume designer Sandy Powell. In an interview with Daily Mail, Powell called it a ‘feat of structural engineering’ with its dramatic silhouette achieved via a corset and a crinoline made of steel under the dress. Over 250 meters of silk crepeline, and yumissima (a very light, and expensive, material that floats when thrown in air), in varying shades of blue were used and decorated with thousands of Swarovski crystals. Finished off with glass slippers, it was a proper fairytale.


20. Keira Knightley’s Green Dress in Atonement

If there’s one thing fans of Atonement remember, it is the green bias-cut evening gown worn by the film’s female protagonist Cecelia, played by Keira Knightley. In the richest emerald silk, it had the glamorous decadence of the ‘30s, and somehow looked both romantic and risqué as it floated by. Conceived by costume designer Jacqueline Durran, the slinky backless number was worn by Knightley’s character Cecilia Tallis in most of the film’s most pivotal scenes. The dramatic energy of the period piece, coupled with the gown’s inimitable elegance, has made it a favorite many times over.

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