MomSkoop
Hollywood has always been more than just movies and stars. It’s a place where fashion moments are born, remembered, and talked about for decades. From billowing white dresses to daring meat gowns, certain outfits have changed how we think about style forever. Get ready to explore the looks that made history and continue to inspire designers, celebrities, and fashion lovers around the world.
1. Marilyn Monroe’s White Halter Dress — The Seven Year Itch (1955)
Standing over a New York subway grate, Marilyn Monroe created a moment that would live forever. The white pleated halter dress by William Travilla caught the wind and became an instant symbol of beauty and Hollywood charm. This wasn’t just a dress—it was magic captured on film.
The scene from The Seven Year Itch turned a simple costume into a cultural treasure. Decades later, the dress still represents everything exciting about Old Hollywood style and remains one of the most recognized outfits in movie history.
2. Audrey Hepburn’s Black Givenchy Dress — Breakfast at Tiffany’s (1961)
Elegance found its perfect form when Audrey Hepburn stepped into that black Givenchy dress. Paired with long gloves, layered pearls, and a sparkling tiara, Holly Golightly’s look became the gold standard for sophistication. Every detail worked together to create something timeless.
Before this film, the little black dress was practical. After Breakfast at Tiffany’s, it became legendary.
3. Grace Kelly’s Powder Blue Gown — Oscars (1955)
Grace Kelly glided onto the Oscar stage in a powder blue Edith Head creation that stopped everyone in their tracks. The clean lines and luxurious silk fabric made her look like royalty, which she would later become.
The dress featured a simple silhouette that let Kelly’s natural beauty take center stage. Its soft color and flawless construction set a new standard for red carpet fashion.
Even today, stylists and celebrities reference this look when they want to achieve true elegance without going over the top.
4. Elizabeth Taylor’s White Slip Dress — Cat on a Hot Tin Roof (1958)
Elizabeth Taylor turned a simple white slip into a fashion statement that shocked audiences. Playing Maggie the Cat, she wore what looked like lingerie as everyday clothing—a bold choice for the 1950s. The dress was minimal, but the impact was massive.
This outfit blurred the line between undergarments and outerwear decades before that became trendy. Fashion designers would later embrace this concept fully, proving that sometimes the simplest pieces make the strongest statements about style and sensuality.
5. Rita Hayworth’s Black Satin Gown — Gilda (1946)
Rita Hayworth’s strapless black satin dress became the definition of postwar glamour. During the famous “Put the Blame on Mame” scene, she paired the gown with long opera gloves that added drama to every movement. The combination was pure seduction wrapped in elegance.
This outfit arrived when the world was ready to celebrate beauty and excitement again after difficult years. Hayworth’s confidence and the dress’s sleek design captured that hopeful energy perfectly.
6. Cher’s Sheer Bob Mackie Dress — Oscars (1986)
Cher arrived at the Oscars wearing a Bob Mackie creation that made everyone gasp. The sheer black two-piece outfit was covered in jewels and topped with a towering feathered headdress that reached for the sky. Nobody had ever seen anything like it on the red carpet.
This bold ensemble challenged every rule about what Oscar fashion should look like. Cher wasn’t trying to fit in—she was making her own statement about creativity and individuality.
7. Madonna’s Marilyn-Inspired Gown — Oscars (1991)
Walking the red carpet with Michael Jackson, Madonna channeled Old Hollywood in a dazzling white sequined gown. The Jean Harlow-inspired dress came with a luxurious fur stole that screamed vintage glamour. She successfully bridged two different eras of entertainment in one perfect look.
The outfit showed that Madonna understood fashion history while making it fresh for the early ’90s. Every sequin sparkled under the lights, creating a connection between classic movie stars and modern pop royalty.
8. Jennifer Lopez’s Green Versace Dress — Grammys (2000)
Jennifer Lopez stepped onto the Grammy red carpet in a green Versace dress that changed the internet forever. The jungle-print gown featured a neckline that plunged daringly low, creating a moment so viral that Google created Google Images to help people find photos of it. One dress literally changed technology.
The bold pattern and daring cut made J.Lo an instant fashion icon. Everyone talked about this look for weeks, months, and even years afterward.
9. Björk’s Swan Dress — Oscars (2001)
Björk arrived at the Oscars wearing something nobody expected: a swan. The Marjan Pejoski dress featured a white gown with an actual swan wrapped around her body, complete with the bird’s head draped over her shoulder. People either loved it or hated it, but nobody could look away.
This outfit became one of the most discussed red carpet moments ever. It challenged the idea that award shows required traditional elegance.
10. Lady Gaga’s Meat Dress — MTV VMAs (2010)
Lady Gaga walked onto the VMA stage wearing an outfit made entirely of raw meat. The dress, constructed from actual flank steak, became an instant sensation that sparked conversations everywhere. Was it fashion? Was it art? Was it activism? The answer was yes to all three.
This shocking look challenged people to think about what clothing could mean beyond just looking pretty.
Gaga used fashion as a statement about rights, identity, and expression. The meat dress became a pop culture phenomenon that proved fashion’s power to start important conversations while making jaws drop across the entire world.
11. Lupita Nyong’o’s Prada Gown — Oscars (2014)
Lupita Nyong’o floated onto the Oscar red carpet in a powder blue Prada gown that everyone immediately called “Nairobi blue.” The Grecian-style dress featured a flowing skirt and a deep V-neckline that created a look both regal and refreshingly modern. She looked like a goddess come to life.
The color was so stunning that it became associated with Lupita herself.
12. Rihanna’s Yellow Guo Pei Gown — Met Gala (2015)
Rihanna arrived at the Met Gala wearing a yellow Guo Pei creation that weighed 55 pounds and featured a train so massive it needed its own team of handlers. The fur-trimmed gown was elaborate, extravagant, and absolutely unforgettable. She understood the assignment and then exceeded every expectation.
The dress immediately inspired countless memes comparing it to pizza, omelets, and Belle’s yellow gown from Beauty and the Beast. But those jokes only proved how much impact the look had.
13. Zendaya’s Joan of Arc Versace Armor — Met Gala (2018)
Zendaya transformed into a modern Joan of Arc at the Met Gala, wearing metallic silver Versace armor paired with a striking auburn bob wig. The gown combined medieval inspiration with high fashion in a way that felt both historical and completely fresh.
This look cemented Zendaya’s reputation as someone willing to take creative fashion risks. The armor-inspired design was bold, the styling was flawless, and the overall effect was breathtaking.
14. Halle Berry’s Sheer Elie Saab Gown — Oscars (2002)
Halle Berry made history as the first Black woman to win Best Actress, wearing a burgundy Elie Saab gown that was equally historic. The sheer dress featured delicate floral embroidery and a design that balanced elegance with modern sensuality.
This gown launched Elie Saab into international fame and became one of the most referenced Oscar dresses ever. The color, the fit, and the moment all came together perfectly.
15. Angelina Jolie’s Black Velvet Versace Gown — Oscars (2012)
Angelina Jolie’s black velvet Versace gown became famous for one reason: the leg. The dress featured a sky-high slit that Jolie posed with repeatedly, creating a meme-worthy moment that dominated social media.
The simple elegance of the black velvet provided the perfect backdrop for that dramatic leg reveal. Jolie knew exactly what she was doing with each pose.
This look demonstrated that confidence and knowing your angles can turn even a classic dress into a viral sensation. The “Jolie leg” became its own pop culture phenomenon overnight.
16. Gwyneth Paltrow’s Pink Ralph Lauren Gown — Oscars (1999)
Gwyneth Paltrow accepted her Best Actress Oscar wearing a pale pink Ralph Lauren ball gown that looked like something from a fairy tale. The romantic dress featured a full skirt and delicate color that divided fashion critics. Some loved it, others thought it was too princess-like, but everyone remembered it.
The gown represented a softer, more romantic approach to red carpet style during the late ’90s. Paltrow’s choice showed that not every Oscar dress needs to be bold or daring—sometimes sweet and dreamy works perfectly.
17. Celine Dion’s Backwards White Suit — Oscars (1999)
Celine Dion walked the Oscar red carpet wearing a white Dior suit—backwards. The tuxedo jacket faced the wrong direction, paired with a matching hat that completed the quirky look. Fashion critics didn’t know what to think, but Dion wore it with complete confidence and a smile.
This outfit became one of the most talked-about Oscar fashion moments, though not always for positive reasons. Years later, Dion defended her choice, saying she was having fun with fashion.
18. Michelle Williams’s Louis Vuitton Gown — Oscars (2012)
Michelle Williams chose a coral red gown that proved simple silhouettes can steal the show. The dress featured delicate detailing and a color that popped beautifully against the red carpet. Williams’s pixie haircut and minimal jewelry let the gown be the star of her look.
The coral shade was unexpected and refreshing among the usual blacks, whites, and metallics of award season. Williams showed that choosing the right color can make a classic dress feel completely fresh and modern.