Awards season is Hollywood’s busiest and most glamorous time in the social calendar. The Academy Awards, better known to most as the Oscars, is one of the biggest Hollywood events.
It brings together class and style to an event that honors acting greats. From Julianne Moore in 1995 to Raquel Welch in 1979, these are the vintage Oscar photos we’ll never forget.
Daryl Hannah
There’s no doubting Daryl Hannah’s beauty as she walked the red carpet at the Academy Awards in 1988.
A young actress with a bright future, she was known for her roles in hit movies like Splash, Roxanne, and the 1989 movie Steel Magnolias.
While Daryl has never won an Oscar, she has appeared in Academy Award-nominated films, making her a red-carpet regular with her impressive looks.
This look from 1988, however, is one of our favorites.
Richard Gere and Cindy Crawford
The relationship between Richard Gere and Cindy Crawford was very much a life-imitating-art scenario that saw the couple fall in love in nearly the same way that Gere and Julia Roberts’ character did in his hit movie Pretty Woman.
Their red carpet appearance in 1991 marked their union as man and wife, and saw the couple very much in love as they smiled and waved to their fans.
Cindy’s red dress was also a nod to the movie, making this a special and noteworthy appearance.
Candice Bergen
Did you know that actress Candice Bergen was a popular model before she started her impressive film career in the ’60s?
Her appearance at the 1973 Academy Awards was unsurprising as she strutted her stuff, looking flawless.
Presenting the award for Best Cinematography, Bergen looked regal in a floor-length taupe-colored dress that highlighted her best features and made her look nothing short of confident and glamorous, earning her a spot on our list of the best vintage looks from the Oscars over the years.
Anne Heche and Ellen DeGeneres
Anne and Ellen were the “it couple” of the ’90s, making them both regulars at big Hollywood red-carpet events like the Oscars.
Snapped at the Academy Awards in 1999, the couple looked gorgeous as they entered the venue.
We may question why they chose to wear matching shades on the red carpet. Regardless, their fashionable outfits more than make up for their strange choice of glasses.
It makes them worthy of a spot on our coveted list of Oscar looks from the past.
Madonna
Madonna channeled goddess Marilyn Monroe as she walked the red carpet at the 1991 Academy Awards sporting a blonde coiffe, a fur stole, and pop star Michael Jackson as her date to the coveted award ceremony.
Bagging the coveted Oscar for Best Original Song, the singer later performed her hit “Sooner or Later”.
Billy Porter
Billy Porter makes it onto our list of classic Oscar looks for the brave outfit he wore to the 2019 Academy Awards.
While his choice of a ball gown received mixed reviews, we applaud his courage as he walked down the red carpet at the Academy’s 91st event.
It takes guts to wear something like this, and we think Billy did it with as much flair and grace as possible – donning this outfit and rocking it as only he could.
This ball gown will go down in history and has opened the doors for a new Oscar look.
Lauren Hutton
Lauren Hutton’s Halstead dress was the talking point of the 1975 Academy Awards. Causing quite a stir on the red carpet, the young actress wore a simple pastel dress with a plunging neckline highlighting her delicate features.
Hutton was in attendance to present the award for Best Feature Length Documentary but stole the show with her classic look that has inspired many a red carpet look since her appearance in 1975.
We think her outfit is a winner. Do you?
Julia Roberts and Kiefer Sutherland
A blonde Julia Roberts and her then-beau Kiefer Sutherland were the epitome of Hollywood glam as they rocked the red carpet at the Academy Awards in 1991.
With the paparazzi begging for photos of the two, Julia and Kiefer were all smiles as they attended the event.
Attending for her nomination for her role in Pretty Woman, the actress ditched her red locks in favor of a short blonde hairdo, and the press loved it!
It just goes to show that change can be a good thing, and in Julia’s case, it was a great choice.
Lily Collins
Now a famous actress in her own right, Lily Collins attended the Oscars in 2000 at the tender age of 11 on her father’s arm, singer Phil Collins.
It would be a good few years before Lily made her acting debut, but this look remains a classic.
Phil won Best Song that year for his hit “You’ll Be in My Heart”, a song he wrote and dedicated to his beloved daughter.
He took her along to the event to show her off and celebrate his nomination and win that year.
River Phoenix and Martha Plimpton
A nomination for Best Supporting Actor for the role of Danny Pope in 1988’s Running on Empty saw River Phoenix walk the red carpet of the Academy Awards in 1989.
He was joined by his then-girlfriend Martha Plimpton.
A fairly young actor at the time, River was most known for his role in the 1986 movie Stand by Me, considered a cult classic.
River tragically passed away in 1993, making pictures like this of him suited up even more rare and timeless.
Grace Kelly
Before becoming Princess of Monaco, Grace Kelly was a young actress who turned heads for her beauty and fashion choices.
Donning the now-legendery Edith Head creation, the actress walked the red carpet of the 1955 Academy Awards in style.
This appearance would be one of her last major red-carpet events as she married Monaco’s Prince Rainier only a year later, ending her brilliant film career.
The actress passed away in 1982.
Anthony Hopkins and Charlotte Rampling
Better known to younger fans as the terrifying Hannibal Lecter, Anthony Hopkins was quite handsome in his younger years, as seen in this picture of the actor with Charlotte Rampling at the 1976 Oscars.
Mariah Carey and Whitney Houston
Fans and attendees of the 1999 Oscars were in for a treat! Divas Mariah Carey and Whitney Houston teamed up for a performance at the Dorothy Chandler Pavilion at Los Angeles’s Music Center.
Both were snapped wearing classic white satin gowns. It’s difficult to choose who wore the best dress, making them both worthy of the title of the best-dressed star at the event.
We wish we could have attended the Oscars to see this duo perform together.
Penelope Cruz
Spanish actress Penelope Cruz chose a silky blue Ralph Lauren dress for her red carpet walk during the 2000 Academy Awards in Los Angeles.
The actress, wearing blue eyeshadow to match her dress, looked almost ethereal as she was photographed at the event.
There to receive the award for Best Supporting Actress for her role in Vicky Cristina Barcelona, the actress looked the part of a Hollywood legend.
During her walk on the red carpet, she smiled at the cameras and posed with her coveted figurine.
Cicely Tyson
Cicely Tyson was the epitome of a strong African-American woman throughout her many roles. Her 1977 Honorary Academy Award win would put her on the map as an actress, leading to many more roles in some of showbiz’s hottest movies.
Her outfit choice for the 1977 awards ceremony was iconic! She walked the red carpet wearing a breathtaking white lace dress.
It made her look like the classic actress she was. Sadly Cicely passed away in 2021, leaving behind an impressive legacy.
Diana Ross
Diana Ross took to the stage at the 1985 Academy Awards to perform Stevie Wonder’s hit song “I Just Called to Say I Love You”.
She wore a sparkly gown and the big hairdo she’s most known for.
Ever the glamorous diva, Diana wowed the audience as she sang her unique and now-iconic cover of Stevie’s song, adding a spin to the performance that had people dancing along in the aisles.
And she looked great doing it!
Naomi Campbell
Supermodel Naomi Campbell proved herself worthy of her title when she attended the 1996 Academy Awards.
She wore a draped white satin dress that made her look nothing short of ethereal. While her career has always been successful, much has been said about the model’s mood and temperament.
But, we could almost forgive her for her wrongdoings as we take in the beauty and grace of one of the world’s most beautiful women.
She rocked the red carpet like a pro. Campbell’s outfit is one of the more iconic Oscar looks.
Miyoshi Umeki
Miyoshi Umeki stood out at the 1957 Academy Awards for two reasons. The first was her courage to wear traditional Japanese clothes to a Hollywood event.
To be honest, she absolutely dominated the red carpet that year.
The second came when she became the first Asian actor to win an Oscar. She bagged the award for her hit movie Sayonara.
Miyoshi wowed the audience, and the history books, as she walked the red carpet without a care in the world.
Cher
Cher has been known to wear some pretty crazy ensembles, but the outfit she wore to the Oscars in 1988 takes the cake.
Sporting a barely-there dress that just covered her body, the singer and actress turned heads as she walked the red carpet.
Winning the award for Best Actress for her role in 1988’s Moonstruck, the star made quite a name for herself as she attended the lavish ceremony at the Shrine Auditorium in Los Angeles, making her the perfect candidate for our list of vintage Oscar looks that will always be remembered.
