May 24th, 2011
Celebrity Style, Style File
Saying Goodbye: Oprah Winfrey’s Fashion Through The Years
By The Fashion Bomb Staff

I honestly don’t know what the world will be like without The Oprah Winfrey Show. It has been a fixture in our lives for 25 years and now, sadly, Oprah is leaving her namesake on Wednesday to focus on the growth and development of her nascent Oprah Winfrey Network (OWN).

But as we pour one out for the Oprah Show, let’s take a look back at some of Oprah’s fashion choices through the years:


Before The Oprah Winfrey Show aired, 1985: A relaxed look for a woman who didn’t yet know how powerful she would come to be. Nice boots. I wonder if she still has them?


Her first Daytime Emmy, 1987: So late 80s with the geometric sequined blazer and chunky earrings!


After losing 67 pounds, 1988: On this historic show, Oprah wheels out 67 pounds of fat, representing the weight she lost on the now bogus Optifast diet. She wore a pair of size 10 Calvin Klein jeans she saved from her younger days. I love the simplicity of this outfit, and that fabulous cowboy belt buckle!


Winning her sixth Daytime Emmy award, 1994: Oprah is famous for her yo-yo dieting, and 1994 seems like a slimmer year for her. She is rockin’ the mean Michelle Obama arms her, and I love that ivory corset dress. Add a cone bra, and she’s got a Madonna- approved look!


Singing with Tina Turner, 1997: Oprah says, “I chose a jumpsuit to sing with Tina Turner in 1997. I didn’t want to show my legs. You cannot have your legs being compared with Tina Turner’s!” Fair enough, Ms. Winfrey! This sleek black catsuit was the perfect choice for shakin’ it next to the most fabulous pair of legs the world has seen!


At the 76th Annual Academy Awards, 2003: One of Oprah’s many  figure-flattering gowns. A regal look fit for the queen of daytime!


At her 50th birthday party, 2004: Oprah chose to look like a lady in an ivory tea-time suit. That lace detail on the inside sleeve is divine.


Oprah announces her final season, 2009: Oprah tells the world she would not renew her contract for 2012 in a grey frock. How appropriate that she wore the colour that results in the mix of black and white– sadness and hopefulness for the future. And that bow don’t hurt, either.


Oprah on OWN press tour, 2011: Oprah rocks her queenly robes to her press tour for her newly launched network. I love the collar on this and the deep teal jewel-toned hue. It’s a great look to kick off a great endeavor.


We will definitely miss Oprah. She’s inspired us not only as a woman and philanthropist, but as one of the most influential black people in the world. Can’t wait to see where she takes this network now that she’s going to be working on it full time!


What’s your favorite Oprah look?

Intern 2


images via: abclocal,, The Daily Beast, exposay

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22 Responses to “Saying Goodbye: Oprah Winfrey’s Fashion Through The Years”

  1. Farewell, Queen of Daytime Talk! Here’s to hoping OWN makes its way into my basic cable package (:

    Speaking on topic, I think when you’re Oprah, you can wear whatever you like–you’re still the QUEEN!

  2. Nikki says:

    Go ‘head intern 2! Sooo well written! And I can’t tell you how much I’m gonna miss Oprah.

  3. Maryse says:

    Well done intern 2! I actually like it most when she wears ‘normal’ (though not in my price range) kind of clothes. It just suits daytime television best.

  4. Di says:

    nicely written intern 2 and yes farewell to a great show from a phenomenal woman

  5. Maria says:

    I’m loving this article intern 2. Loving it! Well written, current and a lot of fashion!

  6. artsylee says:

    Love this article! Oprah looks prettier as she ages. :D I especially love that grey farewell dress.

  7. Mari says:

    I will miss mama oprah, that’s for sure!

  8. KBS says:

    Are the other interns working or just #2?
    I wasn’t a huge O fashion fan, but I liked her accessories. Her shoe game has corporate swag and she used to wear this big ole cross necklace and diamond earrings.

  9. missjoie says:

    nice article INTERN 2, i thought claire did this until i read the bottom lol GOOD JOB

  10. chika e. says:

    dear claire,
    just give the intership to intern 2. she is killing it with her well written posts. you know what, just hire her and add her to your wonderful staff. lol oprah style got better as she got older. i’m going to miss her. oh well. good things dont last forever, unfortunately.

  11. Claire says:

    @KBS Each Intern has one day to ‘show their stuff.’ On Monday, Intern 1 blogged. Tuesday, Intern 2 blogged. Today, Intern 3 is blogging. On Thursday, Intern 4 is blogging.
    On Friday, I’ll remind everyone who wrote which posts, and you guys vote on who you think should be the winner of the Fashion Bomb internship and the $1k stipend.

  12. TiP says:

    Bravo intern 2!!! You have been on your “A” game and the other two interns are going to have to bring there “A+” game to get my vote. I have loved Oprah since I was a child and this post shows that when it comes to fashion that Oprah was always on trend(with the times) but not too trendy, dressed for her body(acentuate the positive), and kept the accesories FABOLOUS but to a minimum, cause hey when your wearing 3+ carat Diamond Stud earrings you really don’t need much else. ;) She will be missed!

  13. llehsal says:

    I just love everything here!

  14. MElissa says:

    This is nice but, NY Mag The Cut and the Daily Beast posted almost exactly the same thing a day or two ago…

  15. wallflower says:

    So long Oprah *tears*

    Intern 2- I also thought Claire wrote this until I got to the bottom!

  16. Madpet says:

    I will miss u Oprah. TEARS

  17. Siobhan says:

    Would anyone happen to know the designer Oprah wore on her final show? That pink dress was sooooo beautiful

  18. esme says:

    wow, i also thought claire wrote this. very good post. anyway, i love oprah and i’m going to miss her show. her entire career is such an inspriration. that being said, i never really thought of her as stylish. she had some fashion hits and misses stylewise during her career…mostly misses, though.

  19. Rae says:

    I love her outfit in the 1988 picture!! She looks phenomenal.

  20. [...] She closed out the day with a few Memorial Day themed ‘fits, a news item on an eco-friendly Burberry trench, and a look at Oprah’s fashion throughout the years. [...]

  21. Brenda says:

    The pink dress Oprah wore for her final show is by L’ Wren Scott. I also loved that dress. Intern 2 you are the winner.

  22. [...] dreams. However the simple style does not leave the impression of attractive and luxurious. via & If you have any doubts about legality of content or you have another [...]

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