20 Underboob Moments That Made Fashion History

There is no denying that throughout history there have been moments where fashion and the times were inextricably linked. Think about it: you look at an old photo and just by studying the clothes, you can probably pick up a lot of context around it without knowing what year it was actually from. In fact, certain styles are often defined by their period, like boho chic with the ’70s or minimalism with the ’90s.

But one sign of the times that isn’t necessarily defined by one particular decade is the amount of skin that has become socially acceptable for women to bare. Slowly, hemlines have gotten shorter, fabrics more transparent, and body parts that were once off-limits are finally free to display. Take freeing the nipple for instance: early adopters of the trend like Rita Hayworth and Marlene Dietrich were pioneers of the then-taboo statement. Nowadays, flaunting nipples on the red carpet, albeit still a bold move, is no longer as jarring. And even though it’s more popular today, it’s been going on for years.

In a similar vein, accentuating a little underboob has long been a popular trend amongst style icons, and it’s only gaining more momentum. Celebrities like Madonna, Kate Moss, Naomi Campbell, and Jennifer Aniston can be thanked for daring to rock the trend before it went fully mainstream. Some of the most revealing styles were just simply before their time and took longer to take hold. But with the rise of the digital age and changing views on gender roles, seeing some underboob is hardly a surprise.

But the underboob trend isn’t new. Just take a look back on the most iconic underboob moments that shifted the culture from 1966 until today.

Raquel Welch: 1966

In 1966 actress, Raquel Welch AKA the it-girl of the 1960s and ’70s, appeared in the film The Biggest Bundle of Them All. In it, she posed on a boat wearing a bikini with her underboob peeking out from underneath her top. Welch was known to be a sex symbol at the time but redefined the term by playing strong female characters.

Jane Birkin: 1969

Model and actress Jane Birkin was one of the most photographed women of the 20th century. In an outing with her collaborator and lover Serge Gainsbourg, Birkin attended the Artists Union’s Gala in Paris on April 25th, 1969 wearing a plunging crochet dress without a bra. During a time where it was less socially acceptable, Birkin pushed the envelope for showing her underboob with this before-its-time dress.

Madonna: 1985

Back in the mid-’80s, Madonna had just embarked on her very first tour and was often seen wearing cropped tops that bared her bra. While she didn’t actually show her breasts, it was still a racy move at the time. The singer would go on to wear even more revealing and sometimes nude looks throughout her career.

Naomi Campbell: 1988

English supermodel Naomi Campbell put on a show-stopping display when she walked in Yves Saint Laurent’s Fall/Winter ready-to-wear 1988 show in Paris. Her YSL look consisted of a sheer transparent top with pink sequin embroidery over her breasts. You could see a hint of Campbell’s underboob under the see-through design.

Helena Christensen: 1991

Speaking of the original supermodels, Helena Christensen has also always been a force to be reckoned with inside of the fashion industry. In 1991, Christensen modeled a fishnet Chanel bodysuit designed by Karl Lagerfeld on the Parisian catwalk. Under layers of beaded necklaces, her underboob made a very clear and intentional appearance. It was a show for the books.

Elizabeth Hurley: 1994

There aren’t many dresses in history more iconic than the one worn by Elizabeth Hurley in 1994 — often referred to as that dress. Hurley wore a black safety pin Versace dress with a plunging neckline to attend the premiere of her boyfriend Hugh Grant’s film Four Wedding and a Funeral. Hurley would wear many more cleavage baring looks throughout her time — and even to this day.

Kate Moss: 1996

Kate Moss is no stranger to a controversial trend. In 1996 she walked the Versace Spring 1997 ready-to-wear runway show wearing a little black dress that had a completely sheer bodice — revealing her underboob. Moss would go on to wear even skimpier and more transparent looks throughout her career.

Thierry Mugler: 1998

Thierry Mugler is one of the designers known for really embracing the underboob movement. For his Spring 1998 couture show, he sent a model down the runway wearing a dramatic cutout gown that left little to the imagination. The same dress was later worn by Kim Kardashian in 2019.

Jennifer Lopez: 2000

Jennifer Lopez shocked the world with her infamous plunging green gown at the 2000 Grammy Awards. The dress debuted at Versace during the house’s Spring 2000 ready-to-wear runway show, but it wasn’t until Lopez wore it that it became fashion history. It was such a defining red carpet moment for Lopez that she even modeled an updated version of the gown in 2019 for Versace’s Milan runway show.

Christina Aguilera: 2002

Christina Aguilera stepped onto the stage at the 2002 MTV Video Music Awards to present Eminem with his award for best male music video. For her spotlight moment, she opted for a micro mini denim skirt and a chest-baring crossover halter. Aguilera was known to wear provocative looks at the time as she proudly embraced her sexuality.

Jennifer Aniston: 2003

In 2003, Jennifer Aniston was at the height of her career. Friends was about to begin its 10th and final season, she was married to Hollywood A-lister Brad Pitt, and she had just starred alongside Jim Carrey in a huge commercial hit, Bruce Almighty. Oh, and she was also a style icon. On March 9, she attended the SAG Awards in Los Angeles wearing a sleek minimalist Georgio Armani gown with keyhole cutouts that subtly showed her underboob.

Paris Hilton: 2004

In 2004, Paris Hilton attended the MTV Video Music Awards wearing a silk turquoise cutout gown by Esteban Cortàzar. The Y2K socialite was arguably one of the OG influencers of the digital age and her underboob cutout dress definitely lived up to her trendsetting expectations.

Karlie Kloss: 2013

Fast forward to 2013, when new model on the scene Karlie Kloss attended the Victoria’s Secret after-party following the brand’s annual televised fashion show in New York. Kloss wore an off the shoulder white midi dress with a cutout right along her bust for the affair.

Miley Cyrus: 2014

In 2014 Miley Cyrus was working on shedding her teenage Disney alter ego, Hannah Montana. In an effort to explore her sexuality, the singer wore a provocative strappy Tom Ford gown to an LA charity event. The majority of Cyrus’ torso was left uncovered in the daring black ensemble.

Lady Gaga: 2017

Lady Gaga had jaws dropping when she attended the Grammy Awards in 2017. The Joanne singer performed with Metallica that evening, and definitely dressed for the collab. She served major underboob for her heavy metal night in a two piece set by designer Alex Ulichny.

Emily Ratajkowski: 2019

Emily Ratajkowski has worn her fair share of naked dresses throughout her career. The My Body author attended the 2019 Met Gala wearing one of her most ethereal looks to date. The model wore a custom halter gown by Dundas for the camp-themed night.

Kendall Jenner: 2021

Kendall Jenner walked the 2021 Jacquemus runway in France wearing a short-sleeved cardigan with nothing underneath. The 818 founder is comfortable wearing naked looks that reveal her chest, and this underboob runway moment was no exception.

Zoë Kravitz: 2022

Zoë Kravitz is one of the most stylish actors in Hollywood. For a screening of The Batman in 2022, the actor wore a chic Saint Laurent gown with a scalloped neckline. The main focal point of the dress? Cutouts along her chest revealing the actor’s underboob.

Sydney Sweeney: 2023

Sydney Sweeney’s Alexander McQueen embellished blazer made headlines when she wore the cutout tailored look in early 2023. When the Anyone But You actor posed for a photocall during Berlin’s International Film Festival, her hips and her underboob were completely exposed.

Zendaya: 2024

Zendaya wore some truly iconic looks while promoting her film Dune: Part Two at the start of 2024. One of the standouts was the brown matching set custom designed by Bottega Veneta. The cropped turtleneck top was short enough to graze her boobs making a stunning underboob moment for the books.