Once upon a time, cleavage was the only way to show a little skin. You either hoisted your boobs up for a classic plunge or you didn’t. Sideboob? Underboob? Not even in our vocabulary. Then came the early 2000s — and with it, the rise of the rebellious, subtle, and strangely elegant sideboob.
At first, it felt like a wardrobe malfunction. Tank tops with gaping armholes, slip dresses that clung just right (or wrong). Sideboobing often happened by accident — a threadbare top, a gust of wind, and suddenly you’re showing skin you didn’t intend to. “Oops” became “on purpose,” and soon, sideboob evolved from fashion faux pas to red carpet staple.
Unlike cleavage, which loudly announces itself, sideboob whispers. It’s more fashion statement than seduction tactic — a balancing act of confidence, body contour, and just the right cut of fabric. Women choose to show sideboob for different reasons: to feel sexy, powerful, confident — or simply because the outfit looks amazing and they can pull it off. As Mila Kunis once said, “I showed sideboob. I don’t need to show ass. You get one or the other. You don’t get both.”
The trend quickly caught fire in Hollywood. Stylists embraced it for its sleek sophistication, and celebs like Jennifer Lawrence, Nicole Kidman, and Miley Cyrus brought it to the mainstream — each adding their own twist.
Here, we celebrate 17 memorable red carpet moments that prove sideboob isn’t a mistake — it’s a style move.
1. Amanda Seyfried Stuns in a Shimmering Gucci Mini Dress
Amanda Seyfried pulled a subtle side boob revelation by donning a metallic mini by Gucci.
Amanda Seyfried hilariously reacts with a wide-eyed, awkward grin, perfectly capturing an “oops” moment on the red carpet at the Los Angeles premiere of ‘Lovelace’ at the Egyptian Theatre in Hollywood, Los Angeles, on August 5, 2013 (Credit: WENN)
This high-necked, low-armhole dress gave her enough material to electrify the paparazzi despite a rather conservative-looking dress.
Amanda Seyfried stuns in a shimmering metallic mini dress by Gucci, confidently flaunting subtle side-boob details on the red carpet (Credit: WENN)
2. Carmen Electra Turns Heads in a Bold Saint Laurent Backless Gown
Carmen Electra is not one to make her womanly bits shy away from the cameras, and she certainly didn’t do that at the Latin Grammy Awards 2013 either.
Carmen Electra confidently wows in a daring, backless Saint Laurent gown with a bold side-boob cutout and thigh-high slit, turning heads at the 2013 Latin Grammy Awards on November 22, 2013 (Credit: WENN)
The blonde bombshell proudly showed off her infamous ‘Baywatch’ side boobs in a backless keyhole dress by Saint Laurent. We must say she wore it much better than the model did.
Saint Laurent Embellished Evening Gown, $3,890
3. Jennifer Lawrence Embraces Boldness in a Revealing Dior Dress
The outspoken Jennifer Lawrence once expressed her disgust over young sex selling in Hollywood, but the actress herself put on a Dior dress that was a bit too suggestive to make her claims stand.
The dress, which is probably her most revealing look to date, strategically showed a lot of her side boobs through careful cuts and mesh.
Jennifer Lawrence stuns in a striking black Dior gown with sheer panels and a bold side-boob reveal at the Paris premiere of The Hunger Games: Catching Fire on November 15, 2013 (Credit: WENN)
4. Jessica Biel Radiates Elegance in a Flowing Ruffled Gucci Gown
Mrs. Timberlake doesn’t have many great moments off the red carpet, but we have to admit that she cleans up pretty well on it.
Jessica Biel was spotted wearing a ruffled full-length dress by Gucci that showed a healthy amount of her side bosom and covered up pretty much everything else.
Jessica Biel effortlessly flaunts a chic side-boob moment in a ruffled, full-length Gucci gown at the Hitchcock premiere in Los Angeles on November 20, 2012 (Credit: WENN)
5. Kirsten Dunst Charms in a Chic Louis Vuitton Ensemble
From her pivotal vampire role between two Hollywood big shots Brad Pitt and Tom Cruise, this adorable child actress has indeed come into her own as a woman.
Kirsten Dunst radiates confidence in a backless Louis Vuitton gown, giving a subtle side-boob reveal (Credit: WENN)
Kirsten Dunst revealed how beautifully she has grown up in a Louis Vuitton dress that didn’t do much for her upper half. The then 31-year-old looked absolutely stunning, though.
Kirsten Dunst stuns in a deep-plunge Louis Vuitton gown with an ombré feathered skirt at the PUNK: Chaos to Couture Costume Institute Gala at the Metropolitan Museum of Art in New York on May 6, 2013 (Credit: WENN)
6. Miley Cyrus Pushes Boundaries in a Daring Emilio Pucci Dress
Before Miley Cyrus exploded onto the Hollywood scene as a highly sexualized former Disney kid, the “Wrecking Ball” star had already been showing signs of her sexual outbreak (which only needed a very public breakup to push her over the edge).
Miley Cyrus confidently rocks a daring side-boob look in a strappy black dress paired with her signature edgy blonde hairstyle (Credit: WENN)
The then-21-year-old wore a daring Emilio Pucci dress that almost revealed her nipples. Liam Hemsworth was probably not too happy about this.
Miley Cyrus showcases her bold fashion sense in a revealing black Emilio Pucci dress (Credit: WENN)
We bet Miley was wearing quite a bit of double-sided breast tape!
Miley Cyrus turns heads at Clive Davis’ Pre-Grammy Gala in a dramatic black Emilio Pucci gown with bold cutouts in Beverly Hills on February 9, 2013 (Credit: WENN)
7. Nicole Kidman Exudes Grace in a Stunning Giorgio Armani White Gown
When a true lady such as Nicole Kidman decides to jump on the side boob bandwagon, she makes sure to do it gracefully.
Nicole Kidman exudes elegance as she gracefully shows off the back of her strapless white gown (Credit: WENN)
The then 46-year-old easily gave her younger colleagues a run for their money in a gorgeous white Giorgio Armani gown that revealed quite a bit of her chest.
Nicole Kidman radiates timeless beauty in a plunging white gown, with her classic red lip and soft curls complementing her graceful presence at the Cannes Film Festival (Credit: WENN)
Despite the insanely low neckline (if you can still call it that), Nicole pulled it off with much class.
Nicole Kidman captivates the red carpet at the Cannes Film Festival in a stunning strapless white gown with an elegant plunging neckline and intricate detailing at the waist on May 26, 2013 (Credit: WENN)
8. Rosie Huntington-Whiteley Dazzles in a Ruffled Green Gucci Dress
Rosie Huntington-Whiteley certainly has a penchant for showing off her London fashion.
Rosie Huntington-Whiteley mesmerizes in a flawless beauty look, accentuated by her sleek hairstyle and radiant complexion (Credit: WENN)
This English beauty showed off her couture styling skills by putting on a ruffled green dress by Gucci, which could have easily transformed anyone else into a dinosaur.
Rosie Huntington-Whiteley dazzles in a bold emerald green gown with dramatic ruffles and a daring side-boob reveal (Credit: WENN)
The Victoria’s Secret model put her hair up in a classic bun and slipped her feet into trendy ankle-cuff white heels.
Rosie Huntington-Whiteley stuns in a vibrant emerald green gown with ruffled detailing and a daring thigh-high slit, paired with elegant white heels, making a statement at the LACMA Art + Film Gala (Credit: WENN)
Oh, and we’ll let the pictures do the talking for her side boobs.
Rosie Huntington-Whiteley exudes sophistication in a sleek emerald green gown with delicate ruffle accents at the LACMA 2012 Art + Film Gala honoring Ed Ruscha and Stanley Kubrick presented by Gucci in Los Angeles, California, on October 27, 2012 (Credit: WENN)
9. Sharon Stone Sizzles in a Red Roberto Cavalli Gown
If Nicole Kidman blew us away, the then 55-year-old Sharon Stone was not one to go down without a fight. Despite nearing her senior years, the Hollywood actress revealed a lot of legs and sides in a gorgeous red Roberto Cavalli gown.
Whether that semi-side boob was an intentional reveal or not, we don’t really care. We only care about looking at least half as good as she does when we hit our mid-fifties.
Sharon Stone commands attention in a bold, one-shoulder red gown with daring cutouts and a thigh-high slit, showcasing her ageless beauty and confidence at the de Grisogono party during the Cannes Film Festival on May 21, 2013 (Credit: WENN)
10. Shanina Shaik Shines in a Dazzling Silver Slit Gown
The Australian model did not leave much to the imagination at the 2017 amfAR Gala held during the 2017 Cannes Film Festival at Hotel du Cap-Eden-Roc in Cap d’Antibes, France.
Shanina Shaik dazzles in a metallic silver gown with daring side cutouts and a high slit, effortlessly exuding glamour at the 2017 amfAR Gala during the Cannes Film Festival on May 25, 2017 (Credit: WENN)
11. Selena Gomez Flaunts Confidence in a Sultry Black Dress
While she loves flashing her cleavage, Selena also showed a bit of sideboob at a Flaunt Magazine party at Hakkasan in Beverly Hills, California.
Selena Gomez stuns with a deep berry lip and sultry smoky eye paired with a plunging black dress at a Flaunt Magazine party at Hakkasan in Beverly Hills, California, on November 7, 2013 (Credit: WENN)
12. Maisie Williams Embraces Elegance in a Vibrant Green Dress
The Game of Thrones actress was a vision in green at the Season 7 premiere in Los Angeles.
Maisie Williams radiates elegance in a green dress with a daring side cutout complemented by matching eyeshadow at the Game of Thrones Season 7 premiere at Walt Disney Concert Hall on July 12, 2017, in Los Angeles, California (Credit: WENN)
13. Emma Watson Rocks a Bold Look in a Graphic-Print Brood Dress
The English Harry Potter actress revealed side boob in an edgy Brood Fall 2012 top and skirt at the 2012 MTV Movie Awards.
Emma Watson exudes effortless charm in a bold graphic-print dress with a daring side cutout at the 2012 MTV Movie Awards on June 3, 2012, in Universal City, California (Credit: WENN)
14. Amandla Stenberg Stuns in a Dramatic Black Valentino Gown
The then-19-year-old actress looked stunning with unshaven armpit hair in a dramatic black Valentino gown with a deep neckline.
Amandla Stenberg stuns in a daring black gown with a deep plunge and bold side cutouts, confidently making a statement at the BFI London Film Festival (Credit: WENN)
Accessorizing with Hermes jewelry, she confirmed the decision to go unshaven on her Instagram, captioning a selfie with “#drama #armpit.”
Amandla Stenberg in a revealing black dress at the premiere of her new movie The Hate U Give in London, England, on October 20, 2018 (Credit: WENN)
15. Amanda Holden Impresses in a Lilac Gown with a Flirty Side Cutout
The beautiful Britain’s Got Talent judge dazzled in a lilac one-shoulder dress while attending ITV Palooza at London’s Royal Festival Hall. She completed her look with silver stiletto heels.
Amanda Holden dazzles in a sleek lilac gown with a daring side cutout at the ITV Palooza! at The Royal Festival Hall on October 16, 2018, in London, England (Credit: WENN)
16. Emma Rigby Smolders in a Lace Givenchy Gown
The then 28-year-old actress rocked the same Givenchy lace-paneled wool-crepe gown Jessica Chastain wore to the 2018 Palm Springs International Film Festival Awards Gala.
Emma Rigby flashes sideboob in a lace gown at the World Premiere of ‘The Festival’ at Cineworld Leicester Square on August 13, 2018, in London, England (Credit: WENN)
17. Laura Crane Channels Retro Vibes in an 80s Style Floral Pinafore Dress
The professional surfer/model left her fans speechless in black strappy sandals paired with a floral 80s-style pinafore dress from Topshop.
Laura Crane showed off her incredible boobs at the European Premiere of Disney’s ‘Christopher Robin’ at BFI Southbank on August 4, 2018, in London, England (Credit: WENN)
From daring designer gowns to edgy jumpsuits, these celebrities prove that the sideboob trend is more than just a fleeting fashion moment — it’s a confident style choice that blends elegance with allure. And as always, it’s the right pair of shoes that completes the look, grounding even the boldest outfit in red carpet sophistication.
Whether subtle or striking, these looks remind us that fashion is about expression — and there’s no wrong way to show a little skin when you’re stepping out in style.
Stepping Out in Style: Celebrities Flaunting Sideboob With Stunning Footwear
The sideboob trend has become a daring yet elegant fashion statement on red carpets. Let’s explore how various celebrities have embraced this trend, pairing revealing outfits with remarkable footwear.
Joey King Turns Heads in a Cutout David Koma Dress
- Event: 49th AFI Life Achievement Award
- Outfit: Joey King donned a provocative black cutout dress by David Koma, featuring a halter neckline and significant midriff and chest cutouts, showcasing her inner sideboob.
- Footwear: She accessorized with Andrea Wazen heels, adding a touch of elegance to her edgy ensemble.
- More Details: Joey King’s daring David Koma look
Saoirse Ronan Dazzles in a Slinky Celine Gown
- Event: 77th Annual Golden Globe Awards
- Outfit: Saoirse Ronan stepped out in a sequin-embellished floor-length gown by Celine, featuring a plunging cowl neck and open back, offering a hint of sideboob.
- Footwear: She completed her look with strappy gold sandals from Celine, perfectly complementing her shimmering dress.
- More Details: Saoirse Ronan’s glamorous Celine ensemble
Miley Cyrus Sparkles in a Low-Cut Saint Laurent Dress
- Event: 2019 Vanity Fair Oscar Party
- Outfit: Miley Cyrus flashed sideboob in a sparkling black dress from Saint Laurent by Anthony Vaccarello, featuring a daring low-cut design.
- Footwear: She paired the dress with black ankle-strap sandals, adding a classic touch to her bold look.
- More Details: Miley Cyrus’s shimmering Saint Laurent appearance
Zendaya Stuns in a Spiderweb Valentino Haute Couture Dress
- Event: ‘Spider-Man: No Way Home’ Premiere
- Outfit: Zendaya bared some sideboob in a custom Valentino Haute Couture spiderweb dress with a plunging neckline and thigh-high slit.
- Footwear: She complemented her ensemble with black Christian Louboutin So Kate crystal heels, enhancing the glamour of her outfit.
- More Details: Zendaya’s captivating Valentino look
Julianne Hough Radiates Elegance in a White Georges Hobeika Jumpsuit
- Event: International Day of the Girl Celebration
- Outfit: Julianne Hough showcased sideboob in a short-sleeved white jumpsuit from Georges Hobeika’s Spring 2014 Couture collection, featuring a pearl-embellished bodice and illusion plunging neckline.
- Footwear: She paired the jumpsuit with white satin “Popp” sandals by Jerome C. Rousseau, adding a sophisticated finish.
- More Details: Julianne Hough’s chic Georges Hobeika ensemble
These instances highlight how celebrities confidently embrace the sideboob trend, pairing daring outfits with stylish footwear to make memorable fashion statements.