This list may be proof that not only are men from Mars and women are from Venus, they are even more distant from each other, like from Mercury and the outer Moons of Jupiter. Perhaps it’s evidence the female mind is more highly evolved. There is not a male neuron on the planet that understands the joy that apparently comes with spending a decade’s income on an elaborate piece of clothing that A) requires a starvation diet to get into and that B) is worn only once for a few hours. Yet most would be forced to admit they can make for heavenly sights. Even in Greek legends of long ago, the colour red was denied mere mortals because the dye was the most difficult and expensive to make.
Some dresses are true works of art. For those readers without advanced economics degrees, the crack research unit here at The Richest has converted the prices into current U.S. dollars to make comparisons easier and more accurate. Ten grand in the 1950s was still a whole bunch of money. Another major factor in putting a price on a dress is who wore it. Let’s face it, that killer frock your Aunt Agatha wore to the Bowling Awards in Cleveland is going to be worth less than the one in which a real royal married in. If you were to go to an auction to spend more for a dress than normal people spend on a house, which one would you buy?
20 Charlize Theron, $107,000
Some smokin’ white heat from the South African Oscar-winning actress. Technically it's a white silk bustier dress from Dior Haute Couture with, according to Red Carpet Fashion Awards, an embroidered peplum. Theron is worth over $100 million, so the hundred grand she shelled out at the time for her fancy frock was a drop in the fashion/marketing budget for her. The minimal makeup, understated diamond stud earrings, and short hair that beautifully accentuate her looks probably cost a bundle, but the flawless skin, amazing cheekbones, and killer figure, on the other hand, are priceless.
19 Anne Hathaway, $110,000
She may not have made the best co-host that year. The term “cringe-tastic” was used. But she owned the red-carpet entrance ceremony in a striking red silk Valentino gown. She barely makes the cut since it cost a mere 80 grand at the time. But that’s over a hundred grand today. Plus, that little bauble of a necklace she borrowed from Tiffany’s that night was worth a few millions.
That same year she made both the British Vogue’s best dressed as well as Maxim’s hot women list. Two years later, she would win the Best Supporting Actress Oscar for her portrayal of the star-crossed factory girl, Fantine, in the film adaptation of the musical play adaptation of the classic French novel, Les Miserables. Her touching rendition of "Life has killed the dream I dreamed" was, according to Rolling Stones, "volcanic…and has Oscar written all over it.” It catapulted her into a rarified circle of women who won Oscars for a musical role, namely Barbara Streisand, Liza Minelli, and Julie Andrews.
18 Kate Winslet, $122,000
The British actress has been rocking the red carpet for more than a decade. She was still 2 years away from her own Best Actress Oscar (for The Reader) on the night she wore this mint green, form-fitting creation. While Valentino was the one who designed it, it was her daughter who picked it out. It won rave reviews from the red-carpet fashion police. One said she looked like a Greek goddess. No less than Vanity Fair applauded both her choice of the “unlikely” colour and her “old-school elegance and classic lines” reminiscent of Grace Kelly. It reportedly cost $100,000 at the time. The same dress today would cost $122,000. Inflation takes no prisoners. Even for the gods.
17 Princess Diana, $137,000
Lady Diana called it her Mermaid dress, designed by her favourite British designer Catherine Walker, sparkling with sequins and embroidered by the legendary Jakob Schlaepfer, it displayed Diana’s considerable assets in a very un-Royal way. It has been said that no one understood the power of fashion statements than she. While she first wore it on an official visit to Austria, Royal watchers later ascribed a hint of illicit romance in its message. It coincided with the beginning of her affair with her riding instructor James Hewitt as her husband took up with Camilla Bowles. The Daily Mail said, “it was designed to show her off as a dazzlingly desirable woman…s*xuality oozed from every pore.” It sold at auction in 2013 for 90,000 British pounds, the equivalent of about $137,000 today.
16 Audrey Hepburn, $142,750
There are many more elaborate and expensive dresses here but this one has been called the most influential. It was this dress that established Oscar night as the prime publicity venue for actresses and fashion designers. Hepburn won the Oscar for her captivating performance as the unhappy Royal in Roman Holiday. The high neckline and full skirt are modest compared to most others on this list. But modest beauty and on-screen charm were Hepburn’s celebrity trademarks. The successful collaboration with the renowned Hubert de Givenchy made her the epitome of Hollywood elegance. She was so highly regarded that almost 5 decades later, a fan bought it at auction for over $130,000, which is roughly $142,750 today.
15 Lupita Nyong’o, $172,000
Take 6000 pearls or so, Calvin Klein, and People Magazine’s Most Beautiful Woman of 2014, and you have Lupita N’Yong’o at the 2015 Oscar Awards Ceremony. The trilingual, Mexican-born Kenyan Oscar-Award winner was quite a sight. The look on her face when she discovered her pearly frock was stolen from her hotel room must have been something too. Thank goodness there was a happy ending. She showed she’s no intellectual slouch at the 2018 Oscars with her thinly veiled criticism of President Trump’s Immigration policy. She continues her upward trajectory with her starring role in the monster box-office hit, Black Panther. In it, she plays the rebel warrior Nakia. For the Yale grad and martial arts enthusiast who shares her father’s political activism, it would seem to be a perfect fit. Now entering her mid-30s, her talent and character in the newly politicized Hollywood will make her known for a lot more than what she wears
14 Cate Blanchett, $240,000
The award-winning Aussie was a vision at the 2007 Oscars in a single-shoulder, Armani Privé crafted teal and silver gown shimmering with a very expensive fairy dust of Swarovski crystals. Cosmo called it one of the best Oscar dresses ever, extolling how the “gunmetal gown clings to her fabulous body like it was painted on.” If it were a movie, Roger Ebert would give it two thumbs up. It cost $200,000 at the time. The same dress now would be worth more like $240,000. Blanchett’s taste in clothes has long drawn rave reviews from the fashion world. Vogue approvingly noted her avoidance of plain and safe with “a penchant for directional and off-kilter designs, resulting in her status as a fashion maverick rather than a follower of trends.” Also, her tendency to keep winning Oscars and Golden Globes gives her ample opportunity to display her exquisite taste and beauty.
13 Elizabeth Taylor, $248,000
They don’t make stars like Liz Taylor anymore. Her brilliant career, timeless beauty, and tumultuous private life made her a cultural icon. One smitten fashion writer called it “a plunging periwinkle stunner.” It sold at auction in 1999 for $167,000. Today, that would be almost a quarter of a million bucks. Her later life was a train wreck with too much alcohol and too many husbands. She scandalized the world with her affairs and conspicuous consumption. The great Johnny Carson said she held an unmatched fascination for the international public. She made her first film during World War 2 but her celebrity status lasted for 50 years, long enough to be on The Simpsons and be a close friend of Michael Jackson’s. If you want to meet a true giant, check her out on YouTube
12 Paris Hilton, $270,000
She is a woman of large inheritance and meagre accomplishment but give her credit, she has a brand that sustains. She looked like a million bucks at the 2017 Hollywood Beauty Awards with lots of cleavage and skin in an August Getty fashion confection. A few hundred thousand Swarovski crystals added to a lavish effect. She won an award for her successful perfume line, Gold Rush. It’s amazing how letting tapes of yourself leak can boost your personal brand. When you wear a dress worth more than a quarter of a million dollars that took a team of 5 people several months to pull together, life must be good.
11 Princess Diana, $362,454
The British couturier Victor Edelstein was much favoured by Princess Diana. He designed this dark blue velvet gown expressly for her 1985 visit to the White House with Ronald Reagan. Though she danced with the President, it was named the "Travolta dress" because of the famous photo of her dancing with John Travolta. She wore it again posing for her last official portrait in 1997. It was auctioned off twice, the second time in 2013 to a British gentleman who bought it "as a surprise to cheer up his wife.” That’s a lot of cheering up. Hubby paid 250,000 British pounds for it. That’s $362,454 in big bad 2018 US dollars. Let's hope his wife can at least wear it.
10 Amal Clooney, $380,000
HELLO! was alive with alliteration reporting on the wedding of “the Hollywood Heartthrob and Beautiful barrister” in the most romantic of venues: Venice. The barrister showed she can glam with the biggest of celebrities in a romantic off-the-shoulder, ivory dress embroidered with pearls and lace, designed by the Dominican fashion legend Oscar de la Renta. Sadly, it turned out to be the last wedding gown he did before his death. These days, Amal is caring for their twins, donated $500,000 to the March For Our Lives anti-gun student protest in Florida, and is finishing a book on The Right to a Fair Trial in International Law.
9 Kate Middleton, $392,760
An adoring public was quickly on a first name basis with the engaging Royal superstar. Kate was ravishing in the Sarah Burton for Alexander MacQueen dress that was rife with symbolism and tradition. Kate also borrowed and accessorized with the 1936 Cartier Halo diamond Tiara from the Queen herself. Buckingham Palace never stoops to comment on anything so sordid as money, but the dress alone was widely reported t0 be worth 250,000 British pounds, just south of $400,000 today.
8 Kim Kardashian, $523,000
It is a sign of something definitely wrong with the planet when a Kardashian outranks a duchess. But this is a dress, not a character reference. Surely, most people would rather their daughters grow up to be like Kate rather than Kim. Still, it must be said that despite her gong show of a family, Kim looked lovely on her special day in Givenchy Haute Couture, with lace, pearls, and a romantic cathedral-length veil, all designed by the House Creative Director and personal friend of Kanye, Riccardo Tisci. Just the shoes cost $40,000. The entire wedding? $12 million.
7 Beyoncé, $1 Million
The Metropolitan Museum of Art Fashion has an annual event called the Met Gala by those in the know. It is a major red-carpet event with some serious gown wars. At the 2016 Gala celebrating Fashion in the Age of Technology, Beyoncé wore this jaw-dropping Givenchy that hugged her body beautifully thanks to Talalay latex. The pearls were rumoured to cost $8,000 each, too. Some enterprising fashion student claimed to have counted 37 pearls on Queen Bey's left breast alone. If true, that would mean the dress costs $392,000 just from the waist up. Counting is half the fun. We’re being conservative here, but it could easily cost a million bucks.
6 Audrey Hepburn, $1,340,000
The most famous little black dress in the history of little black dresses is by Givenchy himself for Hepburn's star-crossed but adorable character, Holly Golightly in the 1961 rom-com Breakfast at Tiffany’s. It was, in fact, the dress she wore in the opening scene having breakfast from a paper bag outside the locked-up jewellery store where she went to cheer herself up during a case of what she called a type of morning-after discomfort she called “the mean reds.” So endearing was the actress and her portrayal, the dress sold at Christie’s auction house in 2006 for $923,000 In big, bad 2018 US dollars, that’s over a million. And if you don’t tear up when she sings Moon River, you have no heart.
5 Julie Andrews, $1.3 Million
Some people wouldn't be caught dead in a frump getup like this. Someone else might pay a million and a half bucks for it — depends on the day. Could there be a starker contrast from form-fitting latex and pearls? How did such an unglamorous dress get into the top 5? It just proves that who wore it and where can trump the highest of haute couture on the sultriest of stars. Julie Andrews wore it playing a nun0-turned-governess in the hugely popular and much-loved multi-Oscar-winning musical The Sound of Music. Whoever you are, there’s a good chance that it’s your mother’s all-time favourite movie. Obviously, Andrews didn’t win for best wardrobe. But she sang an Oscar-worthy score beautifully. She wore this frumpy alpine outfit to sing her heart out, and fifty years later, it was up for auction and sold for $1.3 million.
4 Nicole Kidman, $3 Million
It’s been named one of the most daring Oscar dresses of all time, though it’s not clear what the most daring thing was — the unforgiving cling on her killer bod, the mink trim, the side slit, or the iridescent chartreuse colour. Or all of the above. The Gibraltar-born European designer John Galliano, then with Dior, pulled out all the stops and established both he and Kidman as creative and respected red-carpet forces to be reckoned with. Too bad he couldn’t do something about that creepy guy beside her. But that was before he went all Scientology on her. Joan Rivers famously yelled at Kidman that the colour made her puke and pretended to retch. Classy lady.
3 Jennifer Lawrence, $4 Million
It’s thought the House of Dior sunk $4 million into their dress for Jennifer Lawrence’s appearance at the 2013 Oscars. The youthful actress made it look like the most expensive prom dress in U.S. history. If that cost came from their marketing budget, they may have got their money’s worth. Their client and her frothy pink strapless full-skirted product got lots of airtime since she not only won her Best Actress Oscar for Silver Linings Playbook, but she also took quite a tumble on her way to get her award. Now one of the wealthiest women in Hollywood, the next time she wants to drop a fortune on a fancy frock, she can just use her debit card.
2 Marilyn Monroe, $4.8 Million
The fashion details pale in comparison to the historical significance. This was the dress worn by Marilyn Monroe at Madison Square Gardens for her legendary rendition of "Happy Birthday Mr. President" for John F. Kennedy’s 45th birthday in May of 1962. The sheer, gold-coloured dress by the Oscar-winning French designer Jean-Louis Berthault featured over 2,000 hand-stitched crystals. Just a few months later, Monroe passed away. Ripley’s Believe or Not, who bought it called it the "most iconic piece of pop culture that there is.” Look it up on YouTube if you haven’t seen the birthday bash.
1 Marilyn Monroe, $6.2 Million
So, Marilyn wins the silver and gold medals at this fashion olympics. And who better? The "Subway Dress" might be the most famous image in movie history. Only the subway grate at 6th and Lexington in New York is still there. Designer William Travilla won an Oscar and Emmy for his work and dressed Monroe in 8 movies, but will be forever remembered as the creator of her so-called "Subway Dress." It’s from an otherwise forgettable movie called The Seven Year Itch in which Marilyn’s character is actually known as "the girl upstairs." Technically, it’s a calf-length cocktail dress in pleated ivory with bodice and deep neckline. Absent Monroe and the updraft it would likely be long forgotten. But here it is, a twentieth-century icon. On the other hand, her husband at the time, baseball legend Joe DiMaggio, was appalled by the whole thing. She soon filed for divorce afterward, charging mental cruelty.