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Home · Hair

Hairstyle File: Oprah's Tress Transformation

She may be known as the queen of all media, but Oprah Winfrey is just as famous for her ever-changing hairstyles. From curls to short bobs, here are over two decades of dazzling 'dos from our Black Women In Hollywood honoree.
By · Updated October 28, 2020
01
1986: Cool Crop

At the 43rd Annual Golden Globe Awards, Oprah rocked a cool short cut with fluffy bangs.

Hairstyle File: Oprah’s Tress Transformation
02
1987: Tease, Please

Teasing the hair out was a popular trend in the 80’s, and at 14th Annual Daytime Emmy Awards, Oprah’s voluminous style was right on trend.

Hairstyle File: Oprah’s Tress Transformation
Getty
03
1988: Eighties Elegance

At the Emmy Awards, Oprah sported a teased-and-sprayed ’do with loads of bouncy layers and shine.

Hairstyle File: Oprah’s Tress Transformation
04
1990: Pretty Fancy

It was a formal affair at the American All-Star Tribute to Oprah Winfrey where the honoree of the night glammed it up with a French twist and layered bangs.

Hairstyle File: Oprah’s Tress Transformation
Getty
05
1995: Casual Chic

At the ‘Get Movin’ With Oprah’ Spring Training Mother’s Day Walk, Oprah looked casually cool in this breezy short style.

Hairstyle File: Oprah’s Tress Transformation
06
1997: Mix It Up

Occasionally, Oprah has worn a wig or hairpiece to create a new look. Here, she goes for short layered pixie at the premiere of Before Women Had Wings.

Hairstyle File: Oprah’s Tress Transformation
Getty
07
1998: Sultry Upsweep

Oprah sported an elegant bouffant upsweep at the 25th Annual Daytime Emmy Awards.

Hairstyle File: Oprah’s Tress Transformation
08
1999: Tress Trendsetter

At the National Book Awards in New York City, Oprah sported a voluminious haircut that started a new trend in hair salons across the country.

Hairstyle File: Oprah’s Tress Transformation
Getty
09
2002: Face-Framing Layers

Oprah was all smiles in soft, face-framing layers and a chic, eyebrow-grazing bang.  A bold red lip adds extra wow-factor to this look.

Hairstyle File: Oprah’s Tress Transformation
10
2002: Turning Heads

Oprah sported a flipped-out short shag packed with body when she arrived onstage at the 54th Annual Primetime Emmy Awards.

Hairstyle File: Oprah’s Tress Transformation
Getty
11
2004: Messy Curls

Oprah attended a charity event in soft spiral curls and peek-a-boo face-framing ringlets.

Hairstyle File: Oprah’s Tress Transformation
12
2004: Star Quality

Oprah looked radiant in these soft, flowing curls at the Sesame Workshop’s Second Annual Benefit Gala.

Hairstyle File: Oprah’s Tress Transformation
Getty
13
2004: Short & Sweet

Oprah stepped out at the Academy Awards in a short layered shag, which became one of her most memorable haircuts during her career.

Hairstyle File: Oprah’s Tress Transformation
14
2005: All Out Glam

Oprah rocked voluminous spiral curls when she got dolled up for the Broadway opening of The Color Purple.

Hairstyle File: Oprah’s Tress Transformation
Getty
15
2005: Golden Goddess

Oprah was a bronze beauty in these sassy short curls and glowing skin at the Academy Awards.

Hairstyle File: Oprah’s Tress Transformation
16
2006: Curly Updo

Oprah wore her curls pulled back in a classy updo at the inauguration of the Hearst Tower.

Hairstyle File: Oprah’s Tress Transformation
17
2006: Stylish Flip

The media mogul wore her hair with the ends flipped and lots of volume when she arrived at her much-talked-about Legend’s Ball.

Hairstyle File: Oprah’s Tress Transformation
18
2007: Va-Va-Volume

Oprah added golden, honey blonde highlights to her lush tresses when she attended the CDFA Fashion Awards.

Hairstyle File: Oprah’s Tress Transformation
19
2007: Sweet Curls

For the premiere of The Great Debaters, Oprah opted for her signature chunky spirals.

Hairstyle File: Oprah’s Tress Transformation
20
2008: Full Spirals

At a charity fundraiser, all eyes were on Oprah as she walked the red carpet in a halo of cascading curls.

Hairstyle File: Oprah’s Tress Transformation
21
2011: Pretty Pony

At an OWN cocktail party, Oprah turned heads in this sophisticated and sleek ponytail with a hint of volume in the crown.

Hairstyle File: Oprah’s Tress Transformation
22
2012: 50s Flair

Oprah looked breathtaking on stage at the O You! event presented by O, The Oprah Magazine. The curvy queen flaunted loads of lovely layers with a slightly flipped curl.

Hairstyle File: Oprah’s Tress Transformation
Ben Rose/WireImage
23
2013: Special Honoree
Oprah Winfrey
Hairstyle File: Oprah’s Tress Transformation
Dave Kotinsky/Getty Images

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