Close Menu
    Sunday, January 19
    Fashion

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    6 Mins Read

    In Oprah we trust!

    Stars and TV personalities may come and go, but Oprah Winfrey has been a comforting and inspiring presence in the lives of Americans for four impressive decades. Over the years, audiences have also watched her style evolve with the eras, from her quintessentially 1980s daytime TV outfits to red carpet hits during the 1990s and beyond.   

    Kelly Hurliman has been Winfrey’s go-to stylist for the last 10 years, ensuring she is reliably turned out in elegant and classic silhouettes. Just like her multi-faceted career, which has seen her host the nation’s most popular talk shows, produce, act, author books, and everything in between, so too is her penchant for fashion always keeping her fans guessing. 

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence.  Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now. 

    In Louis Vuitton at the Golden Globes in 2024

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    To present the final award of the evening at the 81st annual Golden Globes, Winfrey made sure her stage arrival was worth the wait. The multi-hyphenate opted for a custom Louis Vuitton beaded gown, a fitting hat tip to The Color Purple, the film that Winfrey co-produced that had been nominated in various categories that evening. 

    In Dolce & Gabbana at the LA premiere of The Color Purple in 2023

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Winfrey has always been a fan of the hue, but at no time was her love for purple more apparent than during the press run for the remake of The Color Purple. For the Los Angeles premiere, the mogul stepped out in a fitted long-sleeve gown by Dolce & Gabbana with lace shoes, jewels, and even eye makeup all in a matching shade.

    In Versace at the Golden Globes in 2018

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    In January 2018, Winfrey was honored with the Cecil B. DeMille Award in recognition of her outstanding contributions to the entertainment industry. For the milestone achievement, she pulled out all the stops in a striking off-the-shoulder black gown by Versace, which featured ornate embellishments and lace detailing on the neckline. 

    In Vera Wang at the Academy Awards in 2015

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Winfrey was a vision in a frothy frock by Vera Wang on Oscars night in 2015. The dreamy draped light peach dress was only slightly upstaged during the ceremony when someone handed Winfrey a Lego Oscar statuette, which she proceeded to jokingly carry around all night. 

    READ
    Demi Moore attended the closing ceremony of the 2024 Cannes Film Festival while repping the coquette trend in a black gown with a huge bow.

    In Badgley Mischka at the Screen Actors Guild Awards in 2014

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Winfrey’s commitment to a regal purple moment is unmatched. Case in point: the slinky asymmetrical neckline gown by design duo Badgley Mischka that she wore to the SAG Awards in 2014, made all the more eye-catching thanks to the addition of an oversized brooch. 

    At the NAACP Image Awards in 2014

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Never one to shy away from a bold color, Winfrey sported a joyful shade of orange at the NAACP Image Awards in California. She accessorized her belted shirt dress with her signature accessories: drop-down earrings and a gobstopper-size cocktail ring. 

    In Ralph Lauren in 2011

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    To host a sit down with Ralph Lauren, Oprah Winfrey joined the legendary designer on stage at Lincoln Center in a glamorous scarlet gown with a 1950s-style off-the-shoulder neckline that looked fit for royalty.

    In Oscar de la Renta at the Met Gala in 2010

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Winfrey arrived on the arm of designer Oscar de la Renta for the 2010 Met Gala, kitted out in an embellished and ruched navy ball gown by the man himself.  

    At the Vanity Fair Oscar Party in 2007

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Oprah goes boho! Winfrey made a departure from her usual glamorous red carpet moments at the Vanity Fair Oscars bash in 2007. Instead, Winfrey opted for a more bohemian paisley-patterned number. 

    In Vera Wang at the Legends Ball in 2005

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Winfrey stole the show in a draped pillar box red dress by Vera Wang, accompanied by diamonds and a red lip, while attending the Legends Ball in Santa Barbara in 2005. 

    At the Opening Night of ‘The Color Purple’ in 2005

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    While attending the premiere evening of The Color Purple on Broadway, Winfrey, one of the famed musical’s co-producers, opted for a chocolate brown tea-length taffeta dress, adorned with a purple ribbon waistbelt and trim. 

    At the Academy Awards in 2004

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    For the warmest woman on TV? A cool-toned dove grey dress, as seen here on the talk show icon at the Oscars in 2004. 

    At the Broadcasting and Cable Magazine Hall of Fame Gala in 2002

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Proving that head-to-toe black can be the most effective of all, Winfrey wowed in a sleek long-sleeved turtleneck gown at the Broadcasting and Cable Magazine Hall of Fame Gala.

    At the Daytime Emmys in 1994

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    At the Daytime Emmys in New York City, Winfrey ensured all eyes were on her in a corseted gown with a slightly sheer floral skirt. A fitting choice as she was about to win not one, but two awards for The Oprah Winfrey Show. 

    On ‘America’s All-Star Tribute to Oprah Winfrey’ in 1990

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    Bringing sequins to TV screens all over the country, Winfrey went glam in black sparkles while accepting an award from Bob Hope on the televised special, America's All-Star Tribute to Oprah Winfrey.

    At the 9th Annual National Conference for Women in 1989

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    As the saying goes, go big or go home. Winfrey doubled down on clashing prints and extra teased hair, as well as large gold earrings typical of the time, while at a networking event in New York in 1989.

    At the Daytime Emmys in 1987

    From Versace to Vera Wang, you never know what she will step out in next, but you can be sure it’s fitting of her regal red carpet presence. Read on for a walk down memory lane through some of Oprah Winfrey’s most unforgettable style hits from the 1980s through now.

    It doesn’t get more eighties than a padded shoulder sequin trophy jacket. Winfrey shows us how it was done in the ‘80s, posing with her first-ever Daytime Emmy award in a standout red number. (Fun fact: she has gone on to win 19 additional Daytime Emmys in the decades since.) 

    Share.

    Related Posts