If you want to give your wardrobe a sprinkle of A-list sparkle, then Oprah Winfrey's best looks are an ideal starting point for some sartorial inspiration. The iconic businesswoman has honed a go-to style during her glittering decades-long career in the public eye - including beautiful ruffled gowns, shimmering outerwear, silky tailoring, and cool accessories.
Winfrey began her broadcasting career in radio while in high school and landed a job as a co-anchor for the local evening news at just 19. The rising star then quickly moved into daytime TV, launching a production company along with her iconic The Oprah Winfrey Show in Chicago in 1986. Around this time, she also appeared in Steven Spielberg's The Color Purple - which saw her nominated for a Best Supporting Actress award at the Oscars.
By the mid-1990s, Winfrey had solidified her status as a leading interviewer of everyone from celebrities to royalty. The presenter - who has a long-time partner, the author Stedman Graham - ended her talk show in 2011. However, by this point, she had grown to be one of the wealthiest and most influential women in the world and turned her focus to other areas of media. This included expanding her book club, publishing a magazine and acting in the likes of 2018's A Wrinkle In Time.
Throughout her time on screen, the Hollywood favourite has built up a distinct dress sense that features lashings of colour, swathes of sequins, elegant frocks and sharp power suits. She is proof that you can take your time to find your fashion feet and ultimately find the confidence to have fun with clothes and accessories - whether you are hitting the red carpet or not.
Oprah Winfrey's most unforgettable outfits
Whether you're looking for some of the best dresses for women over 50 or a glamorous way to adopt the latest fashion trends, get inspired by Winfrey's best looks.
1. The slouchy white suit
A tailored suit of some form is a capsule wardrobe must, and we love Winfrey's slouchy white number. At a screening for Maxine's Baby: The Tyler Perry Story in Los Angeles in 2023, Winfrey looked chic in relaxed tailoring. The presenter paired her white blazer jacket and wide-legged trousers with a silky white top and cream boots. She accessorised with wavy locks and silver hooped earrings.
RRP: £278 | Relaxed, comfortable and cool, this set from Reiss works as an elegant co-ord but each piece works as a standalone. The crepe fabric gives this blazer a relaxed fit but the smart tailoring ensures it cinches in at all the right places.
RRP: £178 | Complete the look with these matching wide-leg trousers for an impactful evening (or bridal) look. Swap the blazer for a sparkly top for a less formal vibe.
RRP: £29.50 | Delicate and sophisticated, these silver earrings from Oliver Bonas are a staple in any minimalist capsule wardrobe.
2. The sparkly Oscar de la Renta coat
There was no missing Winfrey as she left the Empire State Building in New York in 2023. The presenter dazzled in a sparkly yellow and purple three-quarter-length coat by Oscar de la Renta, which she paired a silky lilac jumpsuit and sparkly silver trainers.
3. The ruffled navy Met Gala gown
Winfrey exuded elegance at the Met Gala in New York in 2010. The star stepped onto the glamorous red carpet in a sweeping navy gown by Oscar de la Renta, which featured three-quarter-length sleeves, a sparkly bodice and a voluminous ruffled skirt. She accessorised with blue eye shadow and minimal silver jewellery.
4. The silver sequinned dress
All eyes were on Winfrey at the Sidney premiere during the Toronto International Film Festival in 2022. The star opted for a silver sequinned floor-length dress, complete with a shirt-style collar and long sleeves. She accessorised the frock, by Brandon Maxwell, with a high ponytail and metallic heels.
5. The peach midi dress
Winfrey wowed on the red carpet at the Annual Directors Guild Of America Honors in New York in 2004. The presenter looked pretty in a long-sleeved peach-coloured midi dress, which featured a sash neckline and silky fabric detailing. She finished off the elegant ensemble with silver jewellery and a pair of open-toed heels with bow detailing.
6. The bronze sequinned suit
At the premiere of Hulu's The 1619 Project in Los Angeles in 2023, Winfrey shimmered in a bronze-coloured sequinned suit. The star paired the matching Brunello Cucinelli tuxedo-style blazer jacket and tailored trousers with a quirky white blouse and patent kitten-heeled boots.
7. The ruffled orange organza dress
We love a bright colour for the red carpet, and Winfrey stunned in an eye-catching citrus shade at the NAACP Image Awards in Pasadena, California in 2014. She accessorised the orange long-sleeved full-length frock - which featured button-through detailing and ruffles - with dewy make-up and gold drop-down earrings.
8. The chic purple midi dress
Winfrey looked stylish at an Academy Awards Nominee Luncheon in Beverly Hills in 2015. Her magenta long-sleeved midi-dress featured a form-fitting silhouette and square neckline. She accessorised with a metallic clutch and sparkly purple open-toed heels.
9. The casual-but-cool Stella McCartney look
We loved Winfrey's cosy outfit for the Stella McCartney show during Paris Fashion Week in 2019. The star stepped out in a navy long-sleeved floor-length jumper dress, which she cinched in at the waist with a black belt. She accessorised with a black handbag, featuring silver chain detailing.
10. The black velvet trouser suit
Winfrey looked chic at the David Foster Foundation Gala in Vancouver, Canada in 2017. The presenter wore a black velvet suit, featuring a blazer jacket and wide-legged trousers. She paired the ensemble with a white ruffled blouse and a bright pink lip.
11. The floor-length body con dress
The focus was all on Winfrey as she attended the Lawmen: Bass Reeve party in Los Angeles in 2021. For the A-list event, the star wore a long-sleeved dark body con dress, featuring a turtleneck, elegant ruching and a side split. She accessorised the frock with Brunello Cucinelli kitten-heeled boots.
12. The sparkly Ralph Lauren suit
Winfrey dazzled at ELLE's 2023 Women in Hollywood Celebration in Los Angeles in 2023. The star wore a sequinned black suit by Ralph Lauren, which she paired with a silky black top. She finished off the head-turning look with a statement purple handbag - proving the power of a good evening bag - as well as matching heels.
13. The purple SAG Awards gown
Looking every bit the showbiz star, Winfrey stepped out onto the red carpet at the Annual Screen Actors Guild Awards in Los Angeles in 2014 in a slinky purple gown. Her long-sleeved Badgley Mischka design featured a scoop neckline and an eye-catching metallic brooch.
14. The red Vera Wang gown
Winfrey was the epitome of Hollywood glamour at the Legends Ball in Santa Barbara, California in 2005. The star stunned in a sweeping red off-shoulder gown by Vera Wang, featuring elegant draping and a voluminous skirt. She finished off the ensemble with a red lip and silver diamond earrings.
15. The sparkly purple Dolce & Gabbana gown
Winfrey dazzled at the Los Angeles premiere of The Color Purple wearing head-to-toe sequins in her signature hue. The presenter wore a stunning sequinned purple long-sleeved gown, by Dolce & Gabbana, featuring a turtleneck and a small train. She accessorised with glowy make-up and silver drop-down earrings.
16. The patterned monochrome midi dress
Winfrey looked chic in monochrome at The Museum of Modern Arts 2018 David Rockefeller Award Luncheon in New York. The star opted for a black and white patterned midi dress, featuring three-quarter-length sleeves. She kept her accessories simple and completed the look with a pair of black heels.
17. The purple Dolce & Gabanna gown
Winfrey wowed at the Los Angeles premiere of The Color Purple in 2023. The star stepped out in a purple long-sleeved Dolce & Gabanna gown, which featured a side split and a small train. She completed the glam look with a bouncy blow-dry, as well as a matching sparkly purple clutch bag and heels.
18. The glitzy pinstripe power suit
Winfrey wore the ultimate smart casual get-up at the premiere for A Jazzman's Blues in Toronto in 2022. The star wore a black pinstriped power suit for the red carpet event, which she paired with statement red glasses, a long ponytail and leather pointed-toe boots.
19. The navy Versace midi dress
In one of her particularly dazzling looks, Winfrey stepped out in Versace at the premiere of Disney's A Wrinkle In Time in Los Angeles in 2018. The A-lister wore an elegant navy long-sleeved midi-dress, which featured a sweetheart neckline and sparkly detailing. She accessorised with a black clutch bag and sparkly black heels.
20. The black Versace gown
Winfrey stunned at the Golden Globes in Beverly Hills in 2018, where she picked up the Cecil B. deMille Award. The star looked incredible in a sweeping black off-shoulder long-sleeved gown by Versace, which featured lacy detailing around the neckline and a small train. Always one to stay afloat of the latest eyeglasses trends, she finished the look with a pair of black rim glasses which complemented her wavy locks perfectly.
21. The all-white portrait unveiling look
We loved the all-white ensemble that Winfrey wore to the unveiling of her portrait at the Smithsonian National Portrait Gallery in Washington D.C. in 2023. The presenter looked radiant in a dress featuring three-quarter-length sleeves and rosette detailing on the hips. She accessorised with a high ponytail, diamond earrings and a pair of boots.
22. The elegant drop-waist midi dress
Winfrey exuded elegance at the premiere of David Makes Man in Los Angeles in 2019. The star stunned in a white long-sleeved midi dress, featuring a scooped neckline and slouchy silhouette, which she elevated with silver jewellery and a pair of nude heels.
23. The pink royal wedding look
At Prince Harry and Meghan Markle's royal wedding in Windsor in 2018, Winfrey looked pretty in a blush pink dress by Stella McCartney. Her long-sleeved midi featured lacy detailing and an elegant v-neckline, and she accessorised with a matching handbag and buckled heels, as well as a white wide-brimmed hat complete with floral detailing.
24. The champagne-coloured Oscars gown
You can always count on Winfrey to be one of the best dressed stars on the Oscars red carpet. Winfrey looked every bit the glamorous A-lister at the Oscars in 2015. The star graced the red carpet in a floating nude Vera Wang gown, featuring a v-neckline, three-quarter-length sleeves and elegant draping. She accessorised with glossy make-up and statement gold earrings.
25. The emerald green gown
At the Annual Critics' Choice Movie Awards in Santa Monica, California in 2014, Winfrey looked chic in green. Her ribbed-effect dress featured a v-neckline, three-quarter-length sleeves and pleating on the skirt. She accessorised with a black belt complete with bow detailing, gold jewellery and a gold clutch bag.
26. The floaty white gown
Winfrey turned heads at the Los Angeles premiere of Sidney in 2022. The star wore a white long-sleeved shirt-style dress by Brunello Cucinelli, which featured sheer sleeves and a cinched-in waist. She finished off the look with a sleek high ponytail and silver jewellery.
27. The shirt and silky trouser combo
We loved Winfrey's elegant but laid-back outfit for an event at the Festival Of Culture in New Orleans in 2023. The presenter looked stylish in a grey shirt, which she paired with silky silver wide-legged trousers. She accessorised with drop-down pearl earrings and a berry-pink lip.
28. The layered Louis Vuitton look
Winfrey opted for a laid-back glam look at a photocall ahead of the Louis Vuitton Cruise Show 2024 in Stresa, Italy in 2023. She wore a cream striped tunic shirt over a pair of matching wide-legged trousers and finished off the ensemble with a black belt and one of the best Louis Vuitton handbags.
29. The perfectly preppy yellow look
There was no missing Winfrey in a stylish yellow ensemble at The Hollywood Reporter's Empowerment In Entertainment event in Los Angeles in 2019. The presenter wowed in a canary yellow v-necked lightweight knit, which she tucked into a pleated midi skirt. She accessorised with a gold belt and matching heels.
30. The red Stella McCartney gown
Winfrey stunned at the official dinner party that followed the British Academy Film Awards in London in 2014. The star wowed in a vampy burgundy gown by Stella McCartney, which comprised a lacy long-sleeved top and flowing skirt. She finished off the look with glowy make-up and silver jewellery.
31. The jumper and midi skirt combo
You can't go wrong with a fine-knit jumper and midi skirt combo for a smart casual look. Winfrey attended the Los Angeles premiere of Love Is_ in 2018 in a navy knit and a grey three-quarter-length tiered skirt. She accessorised with a sleek ponytail and black heels with silver studded detailing.
32. The fuchsia pink wrap midi dress
Winfrey was channelling Barbiecore well ahead of time. The star stood out at the premiere of Lee Daniels' The Butler in Los Angeles in 2013, in a fuchsia pink long-sleeved midi dress, featuring elegant ruching. She accessorised with silver hooped earrings and a pair of silver heels.
