The Best Natural Diamond Jewelry in the History of the Oscars

Beyonce arrives the 77th Annual Academy Awards on February 27, 2005 in Hollywood, California.(Getty Images)

My favorite season is awards season, and nothing makes a better bookend to the abundance of red carpet occasions quite like the Oscars. Fan-favorite film stars step out in their equally starry natural diamond jewels and couture creations, embodying sheer and unadulterated Old Hollywood razzle-dazzle. 

Rife with sartorial and cinematic milestones, stars celebrate the best in the film industry while delivering the most glamorous and glittering natural diamond jewelry moments. In 1929, the Academy of Motion Picture Art and Sciences began awarding the most lauded artistic achievements in cinema, and ever since, guests have arrived decked out in couture gowns and heart-stopping diamond jewels. 

In the beginning, Oscars jewelry moments were significantly smaller in scale, with stars of the screen often borrowing from the set of their latest project or wearing their own baubles. One such star who loved to rely on her personal jewelry box for the prestigious ceremony is none other than Elizabeth Taylor. The actress wore an antique diamond tiara gifted by her third husband Mike Todd at the 1957 ceremony and the iconic Taylor-Burton diamond in 1970 which consequently inspired other A-listers up the ante when it came to their red carpet diamonds. 

Watched by millions, the Academy Awards allow jewelry houses to get the maximum amount of eyes on their most astounding diamond creations, with many now ingrained into pop culture history. One can’t think of their favorite Oscars jewelry looks without picturing Madonna’s turn as Marilyn Monroe in 1991, drenched in Harry Winston diamonds, or recalling Julia Roberts’ Best Actress acceptance speech in 2001, while she held her head in amazement and victoriously threw her arms up, showcasing her 22-carat diamond Van Cleef & Arpels bangle. The next year, Halle Berry delivered an emotional and poignant speech when she won the Academy Award for Best Actress, picking up her golden trophy with a rare orange pumpkin diamond ring on her finger.

The perfect diamond sparkler has the ability to accelerate a young ingénue’s star power, providing an opportunity to stand out from the crowd, alongside a few bodyguard escorts, of course.

From vintage Fred Leighton diamonds and historical Asprey & Garrard jewels to Bulargi baubles, Chopard sparklers, and Tiffany & Co. creations, the Oscars knows no bounds for the most incredible diamond jewels imaginable. 

Ahead of the 96^th annual awards ceremony on Sunday, we’re looking back on the best natural diamond jewelry ever worn at the Academy Awards.

1957: Elizabeth Taylor

Elizabeth Taylor attended the 1957 Academy Awards with her third husband, producer Mike Todd. She, of course, donned large diamond chandelier earrings and an antique Victorian 1880 diamond TIARA with her romantically pleated chiffon gown. That same year, Taylor pulled out her famed tiara for the Golden Globe Awards and the 1957 Cannes Film Festival as well. In her 2002 book, My Love Affair with Jewelry, the Hollywood icon wrote, “When Mike gave me this tiara, he said, ‘You’re my queen, and I think you should have a tiara.’ I wore it for the first time when we went to the Academy Awards. It was the most perfect night, because Mike’s film Around the World in 80 Days won for Best Picture.” She continued, “It wasn’t fashionable to wear tiaras then, but I wore it anyway because he was my king.” Sadly, Todd passed away almost exactly a year later in a plane crash in New Mexico.

1970: Elizabeth Taylor

One of the most impressive Oscar jewelry moments of all time, Elizabeth Taylor adorned her 69.42-carat pear-shaped diamond, known as the Taylor-Burton or the Cartier diamond, at the 1970 Oscar Ball, wearing a periwinkle V-neck gown by Edith Head. Previously set in a ring, the massive diamond was purchased from Cartier by Taylor’s then-husband Richard Burton for $1.1 million in 1969 and transformed into a captivating necklace. During the ceremony, Taylor presented the award for Best Picture to Midnight Cowboy, dazzling the audience and viewers at home with her new bauble. 

1985: Sally Field

When Sally Field won her second Best Actress Academy Award for Places in the Heart in 1985, she wore a black strapless gown with a delicate diamond bow necklace and diamond cluster earrings, and we have to say, we like it. We really, really like it. 

1991: Madonna

Channeling her inner Marilyn Monroe, the ultimate “Material Girl,” Madonna performed at the 1991 Oscars wearing a white bejeweled Bob Mackie gown and $20 million worth of Harry Winston natural diamonds, including chandelier earrings, thick stacks of diamond bracelets over her white opera gloves, and a mind-boggling diamond necklace. “Talk to me, Harry Winston. Tell me all about it!” Diamonds really are a girl’s best friend.

1996: Angela Bassett

Angela Bassett wore a 273-carat diamond star-burst style Harry Winston necklace, valued at $9 million at the 1996 Academy Awards. Thanks to the jewelry’s high price point, the actress was attended by extra security and was reportedly so anxious about being left alone with the valuable necklace that she asked guards to accompany her to the ladies’ room. 

1997: Salma Hayek

At the 1997 Oscars, Salma Hayek wore a vintage diamond tiara from Fred Leighton, with the help of Rebecca Selva. At the time, Hayek said, “Where else is a girl going to wear a tiara if it’s not to the Oscars?” The actress told Vogue about how her team felt about her decision to wear the diamond headpiece. “Everyone told me I was crazy and that it would be ridiculous, it would be pretentious, and everyone tried to convince me, like my manager, my stylist, and my publicist,” she said. “I wore the tiara anyways, and you know what happened? Everybody started wearing a tiara after that.”

1997: Claire Danes

Solidifying her status as a style icon, Claire Danes subverted black-tie expectations on the 1997 Academy Awards red carpet, wearing a baby blue cashmere t-shirt with a matching Narciso Rodriguez bias-cut silk skirt. While many found the ensemble to be unexpectedly casual, the Romeo + Juliet actress amped up the glamour with an Asprey Daisy Heritage jewelry suite, including a floral necklace with marquise-cut aquamarine petals and pavé fine white round brilliant-cut diamond centers with matching earrings.

1997: Courtney Love

Presenting at the 1997 Oscars during her press junket for The People vs Larry Flynt, Courtney Love wore an angelic white silk Versace gown that she decided to wear at the last minute. The Hole rockstar reportedly spent a lot of time with Buddhist monks ahead of the ceremony to help her choose which colors to incorporate into her look. While they advised her to feature gold, Love went a different route, wearing a platinum and natural diamond lariat necklace from Martin Katz, selected from Beverly Hills jeweler Arianne Phillips. “The necklace was sassy and she’s sassy,” said Katz. “She loved it.”

1997: Celine Dion

Legendary songstress Celine Dion attended the 1997 Academy Awards to perform “I’ve Finally Found Someone” for the A-list crowd, donning a star-worthy look. Dion adorned a glimmering ombré gown and debuted Chanel’s relaunched high jewelry collection. In 1995, Chanel recreated a collection inspired by the only diamond jewelry collection Coco Chanel ever designed in 1932. The Chanel Comète shooting star diamond necklace was made in the exact size and scale as the original. The singer paired the masterpiece with new diamond star studs and was accompanied by four bodyguards. At the time, she joked, “No body looked me in the eye that day. That was the necklace. But I was the lucky one wearing it and I had a great time. I went to bed very late, I just wanted to make sure I was wearing it for as long as I could.”

1998: Gloria Stuart

Gloria Stuart set an Oscars jewelry record at the 1998 ceremony. As the oldest person to ever be nominated for Best Supporting Actress at 87 years old, the Titanic actress wore a 15-carat blue diamond necklace from Harry Winston, paying homage to the “Heart of the Ocean” necklace featured in the film. Reminiscent of the iconic Hope Diamond, the piece remains one of the most expensive pieces of jewelry to take a trip down the red carpet, valued at an incredible $20 million. 

1999: Gwyneth Paltrow

At the 1999 Oscars, Gwyneth Paltrow went home with her new golden trophy and her Harry Winston diamond jewels. Paltrow walked the red carpet in a cotton-candy pink Ralph Lauren gown, teamed with a 40-carat Harry Winston Diamond Princess choker necklace and matching diamond cluster earrings. After winning the Academy Award for Best Actress thanks to her role in Shakespeare in Love, her father, Bruce Paltrow decided to commemorate her win, and purchase the sentimental necklace, despite its $160,000 price tag and the jeweler added in the $25,000 earrings at no charge. She told Vogue, “After I won, my dad, as a present, surprised me with them. Now I’m gonna cry. So, that was very sweet. And, I wore the earrings and necklace when I got married to Brad [Falchuk] in homage to my dad as a way of keeping him there with us.

1999: Jennifer Lopez

Jennifer Lopez attended the 1999 Academy Awards to present the Oscar for Best Original Song in a timeless black silk Badgley Mischka strapless ballgown, paired perfectly with a 100-carat diamond Harry Winston floral wreath necklace and matching diamond earrings. Lopez also adorned an Art Deco-inspired diamond bracelet and a 9.6-carat diamond ring from Fred Leighton. 

1999: Sophia Loren

To present the Academy Award for Best Actor to Roberto Benigni in 1999, Old Hollywood icon Sophia Loren wore two rows of diamonds on her neck, courtesy of jeweler Fred Leighton. The Italian superstar teamed the resplendent necklace with diamond drop earrings.

2000: Queen Latifah

Queen Latifah attended the 2000 Academy Awards wearing a shimmering lavender dress and $5 million worth of Harry Winston diamonds. The star teamed diamond hoop earrings and an impressive sparkler worn on her pinky finger with a breathtaking diamond necklace, featuring a huge pear-shaped diamond. At the time, the New York Times reported that on her way into the famed Vanity Fair after-party, she was told she could not be accompanied by her bodyguard inside the event. To be safe, “She stripped off the several million dollars’ worth of borrowed Harry Winston jewels she had on and handed them to the bodyguard, right on the curb. Like they’re loose change or something.” Ahh, stars – they’re just like us. 

2000: Hilary Swank

Hilary Swank brought home her first Oscar in 2000 for her role in the film, Boys Don’t Cry. To accompany her new golden trophy, the actress wore an equally award-worthy natural diamond necklace from Asprey & Garrard. The piece was originally crafted for one of Queen Victoria’s daughters in 1890 and thanks to its royal origins, can be transformed into a tiara or a series of brooches. Worth over $250,000, the 100-carat diamond piece reportedly helped Swank decide on which dress to wear for the momentous occasion. While stars typically base their jewels on their chosen gown, the unique nature of the necklace made this an exception. Swank wore an iridescent bronze Randolph Duke gown with her regal diamond jewels. 

2000: Chloë Sevigny

Swank’s Boys Don’t Cry co-star Chloë Sevigny also wore impressive (and historic) diamonds from Asprey. Nominated for Best Supporting Actress in 2000, Sevigny adorned a classic black Yves Saint Laurent gown designed by the late Alber Elbaz with a plunging neckline to perfectly showcase her $113,000 natural diamond Maltese cross, originally crafted in 1810.

2001: Julia Roberts

Julia Roberts received the Academy Award for Best Actress thanks to her role in Erin Brockovich in 2001, wearing a black-and-white vintage Valentino couture gown and a 22-carat diamond bracelet on loan from Van Cleef & Arpels and dainty diamond drop earrings.

2002: Halle Berry

In 2002, Halle Berry made Academy Awards history, with a look to match the monumental occasion. The star won the Best Actress Oscar for her role in Monster’s Ball – the first and only Black woman to do so – wearing an Elie Saab gown featuring a sheer floral bodice and burgundy skirt and train, but the real kicker was her ultra-rare Harry Winston pumpkin diamond ring on her pinky finger. The 5.54-carat cushion-cut orange diamond was originally purchased by Harry Winston in 1997 at a Sotheby’s auction on Halloween Eve. Since then, an anonymous buyer purchased the ring from Winston in 2005 for reportedly over $3 Million.

2022: Nicole Kidman

Nicole Kidman wore a petal pink chiffon Chanel Haute Couture frock to the 2002 ceremony and delivered a pretty iconic Oscars jewelry moment. A noted fan of Italian jewelry house Bulgari, Kidman got herself in on the action this time, helping to design the 241-carat rough-cut layered chain choker diamond necklace. At the time, Nicola Bulgari said, “She sketched a wraparound necklace with a tail down the back.” She continued, “We wanted it to look as if it wrapped the neck casually, but the diamonds had to be separated to keep them from scratching one another.” Later valued at $4 million, the co-designed piece was reportedly purchased by an admiring client.

2003: Jennifer Lopez

Lopez arrived at the 2003 Academy Awards arm-in-arm with her now-husband, Ben Affleck not long after their first engagement announcement. That night, the Enough actress debuted one of her best looks to date and one of the most iconic red carpet style moments in all of Oscar’s history. Wearing a one-shoulder embroidered mint green Valentino gown inspired by a dress worn by Jackie Kennedy in 1967. Bringing a touch of bohemian modernity to the ensemble, Fred Leighton whipped up shoulder-scraping chandelier earrings for Lopez to complete her look with 31 carats of diamond briolettes. As a specialty of Fred Leighton at the time, Indian Mughal jewelry inspired the silhouette of the earrings.

2004: Angelina Jolie

Angelina Jolie presented the Oscar for art direction at the 2004 ceremony, wearing a Grecian ivory silk Marc Bouwer gown, but what really stole the show was Jolie’s jewels. The Academy Award-winning actress wore the waterfall Athena necklace from H. Stern, featuring $10 million in D-flawless important diamonds and diamond stud earrings.

2005: Beyoncé

In the early days of their exemplary designer- muse relationship, Beyoncé debuted Lorraine Schwartz’s now trademark handkerchief mesh diamond schoulder-scraping earrings with her sculpted strapless black velvet Versace gown. The earrings featured a fluid setting with languid movement and major impact.

2005: Scarlett Johansson

Scarlett Johansson attended the 2005 Academy Awards wearing a black form-fitting Roland Mouret gown with three vintage diamond star brooches perched in her platinum blonde curly updo on a tiara frame, thanks to Rebecca Selva from Fred Leighton.“[Johansson’s] stylist at the time, Annabel Tollman, said she was thinking about stars for the jewelry,” remembers Selva. “And it all just came together.”

2006: Jennifer Aniston

In her signature effrotless fashion, Jennifer Aniston sported a black Rochas gown with a 137-carat Art Deco diamond necklace from the Bulgari archival Heritage collection at the 2006 Oscars ceremony. A popular bauble among A-listers, the treasure was later worn by Jessica Chastain at the 2014 Golden Globe Awards and Ashley Judd at the 2018 Oscars. It’s been displayed in exhibitions, such as the 2011 Bulgari: 125 Years of Italian Magnificence exhibit at the Grand Palais in Paris as well.

2006: Michelle Williams

Nominated for Best Supporting Actress for her role in Brokeback Mountain in 2006, Michelle Williams’ marigold Vera Wang pleated frock has become a notable fan favorite, along with her stunning vintage Fred Leighton Victorian fringed diamond necklace.

2008: Nicole Kidman

With a knack for exemplary Oscars jewelry, Nicole Kidman wore a black Balenciaga gown at the 2008 ceremony, that acted as a canvas for her mind-blowing diamonds. The actress was covered in a dramatic piece, created L’Wren Scott, with 1,399 carats of rough diamonds in various cuts, shapes, and sizes – 7,645 individual diamonds to be exact.

2009: Penélope Cruz

Winning the Academy Award for Best Supporting Actress in 2009 for her role in Vicky Cristina Barcelona, Penélope Cruz wore a white vintage Balmain dress with a stellar 69-carat cushion-cut graduated diamond necklace by Chopard, along with two diamond bracelets, diamond stud earrings, and a yellow diamond ring from the jeweler. 

2009: Taraji P. Henson

Solidifying her status as a style star, Taraji P. Henson wore a cream-colored Roberto Cavalli gown to the 2009 Academy Awards with a 19th-century diamond floral Fred Leighton necklace, alongside a diamond-laden cocktail ring and diamond drop earrings. Creative director of Fred Leighton, Rebecca Selva told OND, “We have so many memorable moments. The jewelry comes to life when it’s on people. One that stands out is when Taraji P. Henson walked the red carpet for her first major event wearing a Roberto Cavalli dress and a 19^th century diamond flower necklace at the 2009 Oscars. Here was this beautiful young, new star who made the 19^th century part of her story. And walked that red carpet like she owned it.”

2010: Kate Winslet

Kate Winslet looked radiant at the Oscars in 2010, wearing strapless silver Atelier Yves Saint Laurent gown with a $2.5 million Tiffany & Co. Art Deco-inspired necklace featuring a triple-drop pendant with a 13.09-carat rare canary Fancy yellow diamond with matching $975,000 worth of diamond 10-carat Fancy yellow diamond earrings and bracelets. 

2011: Jennifer Hudson

The Dream Girl herself, Miss Jennifer Hudson wowed the crowd at the 2011 Oscars in a tangerine Atelier Versace gown and over 100 carats of Neil Lane diamonds. The actress and songstress wore shoulder-dusting diamond earrings, two captivating cocktail rings, and stacks and stacks of diamond bangles. One wrist featured a diamond and platinum leaf bracelet that weighed in at 35 carats, teamed with a sparkling diamond tennis bracelet. The other adorned two wide Art Deco-inspired diamond and platinum bangles, valued at over $300,000. 

2012: Natalie Portman

Natalie Portman channeled Old Hollywood glamour at the 2012 Oscars, wearing vintage Dior Haute Couture while covered in natural diamonds from Harry Winston. The star adorned a 100-carat diamond necklace, appropriately dating back to 1954 in keeping with her archival frock. The necklace’s cluster design was still considered new at the time of its creation. Now, its one of the jeweler’s most memorable trademark styles. Portman added a pair of stunning 11-carat diamond drop earrings and showed off what was then her brand-new diamond wedding ring.

2013: Jennifer Lawrence

Winning Best Actress for Silver Linings Playbook, Jennifer Lawrence famously tripped over her voluminous Christian Dior Couture ivory number while climbing the ceremony steps to receive her Academy Award in 2013. The actress took her memorable a few steps further with loads of Chopard natural diamonds. Lawrence wore 12-carat diamond drop earrings and a captivating ring, but what really completed the ensemble was her thin, traipsing necklace with 74 carats worth of diamonds, draped along her clavicle. With 150 diamond stones, the long necklace cascaded down her back.

2013: Anne Hathaway

Anne Hathaway won the Best Supporting Actress Oscar in 2013 for her turn as Fantine in Les Misérables, wearing a soft pink Prada gown, diamond stud earrings, and a victory-worthy Tiffany & Co. floral diamond necklace that elegantly dangled down her back. The jewel looked just perfect with the crisscross strap detailing of her gown.

2014: Lupita Nyong’o

Then-breakout star Lupita Nyong’o took home the coveted golden statue for her role in 12 Years a Slave at the 2014 Academy Awards wearing an ethereal sky-blue pleated Prada gown and Fred Leighton diamond jewels, including a diamond-encrusted gold headband and matching cluster diamond earrings. The collective craze over her headband was so intense, there was even a Twitter page (@lupitasheadband) created in honor of the gorgeous piece.

2015: Margot Robbie

At the 2015 Oscars ceremony, Margot Robbie let her diamonds do the talking. The Barbie star wore the famous Van Cleef & Arpels Zip Antique Columbine necklace. 150 natural brilliant-cut diamonds and 300 sapphires are attached to the golden zipper. The piece popped against her black plunging Saint Laurent dress, leading to the jewel to saturate headlines. Dating back to 1950, the idiosyncratic design was created at the suggestion of the Duchess of Windsor and can be worn unzipped as a necklace or zipped up, as a bracelet. Worth $1.5 million dollars, Robbie joked that night, “This necklace is worth more than my life!”

2017: Jessica Biel

Jessica Biel opted for an almost $2 million necklace for an electric Oscars jewlery moment in 2017. The Tiffany & Co. piece was chosen from the house’s rainforest-inspired Art of the Wild collection. The necklace reportedly took nearly a year to create. Featuring a collar of 200 baguette-cut natural diamonds, weighing in at around 60 carats, the jewel frays out with 350 gold fronds with diamonds scattered throughout.

2017:  Taraji P. Henson

Taraji P. Henson looked every bit the bombshell at the 2017 ceremony, wearing a navy velvet off-the-shoulder Alberta Ferretti gown and over 103 carats of diamonds from Nirav Modi. The Hidden Figures star wore the designer’s Luminance necklace – with natural diamonds in varied cuts and shapes, the three-dimensional show-stopping piece took over 700 hours to handcraft.

2019: Lady Gaga

A legendary Oscars jewelry moment, Lady Gaga walked the red carpet in 2019 in a dramatic black Alexander McQueen gown and later changing into a Brandon Maxwell creation, all the while sporting the 128.54-carat diamond Tiffany & Co. necklace. Last worn by Breakfast at Tiffany’s star Audrey Hepburn during the film’s press tour, the massive yellow diamond had only been publically worn three times (ever.) A socialite wore the historic jewel for a fundraiser during the 1950s, then Hepburn, then Gaga. Nominated for Best Actress for A Star Is Born, and Best Original Song for “Shallow,” Lady Gaga grabbed the gold for the latter and make an impact with her diamonds.

2020: Zazie Beetz

Zazie Beetz layered two outstanding Bulgari necklaces on top of one another at the 2020 Oscars. The Joker actress wore a black sequined custom Thom Browne ensemble with a white gold choker including emeralds and white diamonds above a high Divas’ Dream necklace with 78 carats of round-cut diamonds, brilliant-cut and pavé diamonds. She teamed the sparklers with matching earrings and two diamond cocktail rings. Her look in total weighed in at over 120 carats of natural diamonds.

2020: Timothée Chalamet

Timothée Chalamet added some exquisite vintage diamonds on the chest pocket of his navy blue Prada zip-up jacket at the 2020 Academy Awards, which he attended to celebrate Little Women’s nomination for Best Picture. The Dune actor opted for a vintage Cartier London brooch with natural diamonds and Burmese rubies set in platinum and white gold, created in 1955.

2020: Salma Hayek

Reviving her Oscars diamond tiara moment from over 20 years ago, Salma Hayek arrived at the 2020 Academy Awards wearing a pavé-set diamond and South Sea pearl laurel wreath necklace by Boucheron in her hair so it resembled a pearl and diamond tiara. The star topped off her regal look with matching pearl and pavé diamond earrings. Like she said in 1997 – “Where else is a girl going to wear a tiara if it’s not to the Oscars?”

2021: Zendaya

Always one to make an entrance, Zendaya’s bright neon yellow cutout Valentino gown hardly took attention from her Bulgari diamond jewels — totaling over $6 million. Styled by Law Roach, Zendaya’s layered necklaces and rings were plucked from the “Magnifica” high jewelry collection, with over 183 carats of natural diamonds. 

2022: Timothée Chalamet

Sans shirt, Timothée Chalamet walked the 2022 Oscars red carpet wearing an open bedazzled lace black Louis Vuitton blazer, showing off his diamond Cartier tennis necklace and the jeweler’s Panthere de Cartier necklace, set with 374 diamonds and two emeralds for the panter’s eyes. The actor further accessorized with several Cartier pavé diamond rings including the Juste un Clou.

2022: Zoë Kravitz

Zoë Kravitz evoked timeless elegance at the 2022 awards show, channeling Old Hollywood icon Audrey Hepburn. The Big Little Lies actress wore a baby-pink strapless column Yves Saint Laurent dress with a 36-carat graduated oval-cut diamond collar necklace from Kwiat and 10-carat diamond stud earrings.

2023: Florence Pugh

Florence Pugh attended the 2023 Academy Awards ceremony wearing a Valentino ensemble and a standout Tiffany & Co. structural natural diamond necklace from the house’s Botanica Orchid Curve high jewelry collection, pink tourmaline drop earrings, and an assortment of dazzling Tiffany Soleste rings.

2023: Cara Delevingne

Cara Delevingne wore a crimson red Elie Saab gown to the 2023 Oscars ceremony, while decked out in Bulgari diamond jewels. The model and actress adorned over 80 carats of natural diamonds, with a stunning three-strand Serpenti snake necklace wrapped around her neck and matching diamond earrings for the occasion.

2023: Michael B. Jordan

Michael B. Jordan arrived on the red carpet in 2023 looking incredibly dapper in a Louis Vuitton tuxedo with not one, but two massive Tiffany & Co. diamond “Bird on a Rock” brooches, designed by Jean Schlumberger. Along with diamond stud earrings, a diamond tennis bracelet, and a diamond ring, the actor’s iconic bird brooches are what caught our eye. While one pavé diamond bird sits atop a pink morganite gemstone, the other is perched above a 58-carat green tourmaline stone.